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Synthesis of novel triiodide ionic liquid based on quaternary ammonium cation and its use as a solvent reagent under mild and solvent-free conditions Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Mahnaz Sakhdari,Nadiya Koukabi,Mohammad Ali Zolfigol
Abstract In this article, for the first time, N,N,N-triethyl-3-iodopropan-1-aminium triiodide [N2223I] [I3] was synthesized and utilized as both a reagent and a solvent in combination with H2O2 (35%) to convert aromatic compounds into their corresponding iodo derivatives. The iodination was accomplished in the absence of organic solvents, and in most instances, water was the sole extraction solvent
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Eelectrosynthesis of benzothiazole derivatives via C–H thiolation Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Reza Ahdenov,Ali Asghar Mohammadi,Somayeh Makarem,Salman Taheri,Hoda Mollabagher
Abstract Benzothiazole derivatives are essential intermediates in synthesizing a wide variety of medical and pharmaceutical compounds, and there is a great demand for a simple and efficient method to synthesize benzothiazoles under mild reaction conditions. Organic electrosynthesis as an energy-efficient process represents an environmentally benign and safer method than traditional methods for organic
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Ionic liquid-catalyzed synthesis of (1,4-benzoxazin-3-yl) malonate derivatives via cross-dehydrogenative-coupling reactions Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Ali Sharifi,Maryam Moazami,Mohammad Saeed Abaee,Mojtaba Mirzaei
Abstract A convenient C(sp3)–C(sp3) oxidative dehydrogenative coupling reaction of 1,4-benzoxazin-2-ones with malonate esters was developed under mild conditions to obtain the respective ester malonates in high yields. Reactions take place in [omim]FeCl4, acting as both the solvent and the catalyst. Under [omim]Cl/FeCl3-DDQ conditions, derivatives of 1 coupled with malonate 2 to give the target molecules
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Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Atsushi Tarui,Erika Kamata,Koji Ebisu,Yui Kawai,Ryota Araki,Takeshi Yabe,Yukiko Karuo,Kazuyuki Sato,Kentaro Kawai,Masaaki Omote
Abstrtact A series of 2,2-difluoro-2-arylethylamines was synthesized as fluorinated analogs of octopamine and noradrenaline with the expectation of bioisosteric OH/F exchanges. The syntheses of these compounds were performed by a Suzuki–Miyaura cross-coupling reaction of 4-(bromodifluoroacetyl)morpholine with aryl boronic acids to produce the intermediate 2,2-difluoro-2-arylacetamides, followed by
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Two independent and consecutive Michael addition of 1,3-dimethylbarbituric acid to (2,6-diarylidene)cyclohexanone: Flying-bird-shaped 2D-polymeric structure Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Nader Noroozi Pesyan,Saman Mousavi,Ertan Şahin
Abstract Two independent and consecutive intermolecular Michael addition of 1,3-dimethylbarbituric acid to 2,6-diarylidenecyclohexanone as an α,β-unsaturated ketone leads to synthesis of a new type of meso form 5,5′-((2-oxocyclohexane-1,3-diyl)bis(arylmethylene))bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) in good yield. These compounds showed a 2D-polymeric structure via intermolecular H-bonds
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Cyclization of N-acetyl derivative: Novel synthesis – azoles and azines, antimicrobial activities, and computational studies Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Eman O. Hamed,Mohamed G. Assy,Nabil H. Ouf,Doaa A. Elsayed,Magda H. Abdellattif
Abstract 2-Pyridone is considered as one of the most famous efficient pharmaceutical compounds. Many approaches were discovered to synthesize 2-pyridone. In this present research, chloroacetylation of benzylamine at simple conditions, EtONa/EtCOONa produced N-benzyl-2-chloroacetamide 2. Compound 2 was allowed to react with different reagents. These reagents are acetylacetone, ethyl cyanoacetate, ethyl
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Study of the reactivity of aminocyanopyrazoles and evaluation of the mitochondrial reductive function of some products Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Soumaya Bellili, Nicholas J. Coltman, Nikolas J. Hodges, Fatma Allouche
This research investigated the general high-throughput synthetic protocol for the accelerated synthesis of functionalized trifluoromethylpyrazolopyrimidines 3 and N -(5-cyano-3-methyl-1-phenyl-1 H -pyrazol-4-yl) benzamide 4 from aminocyanopyrazole 1 precursors. The action of chlorosulfonyl isocyanate (CSI) with aminopyrazolo[3,4- d ]pyrimidines 2 was found to produce triazolopyrimidinones 5 . The MTT
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“Click” assembly of novel dual inhibitors of AChE and MAO-B from pyridoxine derivatives for the treatment of Alzheimer’s disease Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Zhao Jia, Huiyun Wen, Saipeng Huang, Yane Luo, Juanjuan Gao, Ruijie Wang, Kaikai Wan, Weiming Xue
This study fast synthesizes numerous functionalized pyridoxines using click chemistry and assayed in vitro as inhibitors of the acetylcholinesterase (AChE), butyrylcholinesterase, and two monoamine oxidase (MAO) isoforms, MAO-A and MAO-B. Most of the obtained compounds demonstrate good AChE and selective MAO-B inhibitory activities in the micromolar range, especially one compound, called 4k5 , exhibits
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Sono and nano: A perfect synergy for eco-compatible Biginelli reaction Heterocycl. Commun. (IF 2.3) Pub Date : 2022-01-01 Marzieh Tahmasbi, Nadiya Koukabi, Ozra Armandpour
In this study, we evaluated the performance of nano-γ-Fe 2 O 3 –SO 3 H catalyst in the Biginelli reaction and synthesized 3,4-dihydropyrimidine-2-(1 H )-ones. This reaction was carried out under solvent-free and ultrasonic irradiation conditions and belonged to one-pot multicomponent reactions (MCRs) with an adopted aromatic aldehyde, ethyl acetoacetate, and urea as starting materials for the beginning
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Design, Synthesis and Biological Evaluation of N-((2-phenyloxazol-4-yl)methyl) Pyrimidine Carboxamide Derivatives as Potential Fungicidal Agents Heterocycl. Commun. (IF 2.3) Pub Date : 2021-02-16 Danling Huang, Shumin Zheng, Yong-Xian Cheng
Twelve N-((2-phenyloxazol-4-yl)methyl) pyrimidine carboxamide derivatives were designed, synthesized, and characterized by 1H NMR, 13C NMR, and HRMS. The fungicidal activities of these new compounds against Sclerotinia sclerotiorum, Botrytis cinereal, and Colletotrichum fragariae were evaluated. The results indicated that compounds 5b, 5f, and 5g displayed potential fungicidal activities against tested
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Anticancer activity of novel Schiff bases and azo dyes derived from 3-amino-4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione Heterocycl. Commun. (IF 2.3) Pub Date : 2021-02-16 Abdeltawab Mohamed Saeed, Shaikha S. AlNeyadi, Ibrahim M. Abdou
New Schiff bases and azo dyes derivatives have been synthesized via appropriate conventional methods using pyranoquinolinone as a starting material. The compounds obtained were characterized by spectral analysis and evaluated for anticancer activity in several human tumor cell lines: MCF-7 breast cancer, HepG2 liver cancer and HCT-116 colon carcinoma. 5-fluorouracil was used as a reference drug. The
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Para toluenesulfonic acid-catalyzed one-pot, three-component synthesis of benzo[5,6]chromeno[3,2-c]quinoline compounds in aqueous medium Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Naser Sadeghpour Orang,Hadi Soltani,Mehdi Ghiamirad,Mehdi Ahmadi Sabegh
Abstract A new series of benzo[5,6]chromeno[3,2-c]quinoline derivatives were successfully synthesized using various arylglyoxal monohydrates, quinoline-2,4-dione, and β-naphthol in H2O:EtOH (2:1) as a green solvent in the presence of catalytic amounts p-toluenesulfonic acid as a mild catalyst under reflux conditions with high yields (83–92%). The reaction conditions were optimized in different solvents
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Design, synthesis, and biological evaluation of phenyl-isoxazole-carboxamide derivatives as anticancer agents Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Mohammed Hawash,Nidal Jaradat,Noor Bawwab,Kamilah Salem,Hadeel Arafat,Yousef Hajyousef,Tahrir Shtayeh,Shorooq Sobuh
Abstract The present study aimed to design and synthesize a series of phenyl-isoxazole-carboxamide derivatives and investigate their antitumor and antioxidant activities. The in vitro cytotoxic evaluation was conducted using the MTS assay against four cancer cell lines: hepatocellular carcinoma (Hep3B and HepG2), cervical adenocarcinoma (HeLa), breast carcinoma (MCF-7), in addition to the normal cell
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Design and microwave-assisted synthesis of a novel Mannich base and conazole derivatives and their biological assessment Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Yıldız Uygun Cebeci,Şengül Alpay Karaoğlu
Abstract 4-Amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (1) was converted to the corresponding Schiff base (2) by treatment with salicylaldehyde. 1,2,4-Triazoles were then converted to the corresponding Mannich bases containing fluroquinolone core using a one-pot three-component procedure. Moreover, the synthesis of six compounds, which can be considered as conazole analogues, was performed starting
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Quantum chemical calculations of phenazine-based organic dyes in dye-sensitized solar cells Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Nesim Yigit,Zeynep Şilan Turhan
Abstract In this study, quantum chemical calculations of phenazine-based organic molecules applied in organic dye-sensitized solar cells (DSSCs) have been made and interpreted. Since DSSC molecules work with the electron push–pull system, the sequence of other compounds (2–8) from compound 1 is designed as a donor–π bridge (weak acceptor)–acceptor (D–π–A). Later, the studied molecules were expanded
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Quantum chemistry study on the promoted reactivity of substituted cyclooctynes in bioorthogonal cycloaddition reactions Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Tayebeh Hosseinnejad,Marzieh Omrani-Pachin
Abstract In the present research, we focus on the energetics and electronic aspects of enhanced reactivity in the regioselective bioorthogonal 1,3-dipolar cycloaddition reaction of various substituted cyclooctynes with methyl azide, applying quantum chemistry approaches. In this respect, we assessed the structural and energetic properties of regioisomeric products and their corresponded transition
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Synthesis, characteristic fragmentation patterns, and antibacterial activity of new azo compounds from the coupling reaction of diazobenzothiazole ions and acetaminophen Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Joseph Tsemeugne,Pamela Kemda Nangmo,Pierre Mkounga,Jean De Dieu Tamokou,Iréne Chinda Kengne,Giles Edwards,Emmanuel Fondjo Sopbué,Augustin Ephrem Nkengfack
Abstract In this study, a series of azobenzothiazole dyes 4 were synthesized via diazotization of substituted benzothiazole derivatives followed by azo coupling with acetaminophen. The chemical structures of all synthesized compounds were confirmed using analytical data and spectroscopic techniques, including UV-visible, IR, mass spectra, and 1H- and 13C-NMR. The in situ formed diazobenzothiazole ions
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Magnetic nanoparticle-supported sulfonic acid as a green catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Mahnaz Sakhdari,Ali Amoozadeh,Eskandar Kolvari
Abstract In this work, magnetic nanoparticle-supported sulfonic acid (γ-Fe2O3-SO3H) is used as an efficient catalyst in the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in a short time (40–70 min for trisubstituted imidazoles and 30–40 min for tetrasubstituted imidazoles) and high-purity products were obtained (92–98% for trisubstituted imidazoles and 94–98%
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Quantum chemical studies on structural, spectroscopic, nonlinear optical, and thermodynamic properties of the 1,2,4-triazole compound Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Hilal Medetalibeyoğlu,Haydar Yüksek
Abstract In this study, the structure of 4-[4-(diethylamino)-benzylideneamino]-5-benzyl-2H-1,2,4-triazol-3(4H)-one (DBT) was examined through spectroscopic and theoretical analyses. In this respect, the geometrical, vibrational frequency, 1H and 13C-nuclear magnetic resonance (NMR) chemical shifts, thermodynamic, hyperpolarizability, and electronic properties including the highest occupied molecular
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Design and development of novel thiazole-sulfonamide derivatives as a protective agent against diabetic cataract in Wistar rats via inhibition of aldose reductase Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Liang Yin,Mingxue Zhang,Tiangeng He
Abstract In recent years, ALR2 (aldose reductase) inhibitors have attracted attention for their effective ability to reduce the progression of diabetes-associated cataracts. Therefore, in the present article, we intended to develop novel thiazole-sulfonamide hybrids as a potent inhibitor of ALR2. These molecules significantly inhibited the ALR2 level in the rat lenses homogenate, where the most potent
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Synergistic promoting effect of ball milling and Fe(ii) catalysis for cross-dehydrogenative-coupling of 1,4-benzoxazinones with indoles Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Ali Sharifi, Zahra Babaalian, M. Saeed Abaee, Maryam Moazami, Mojtaba Mirzaei
In this work, a novel C(sp 3 )–C(sp 2 ) cross-dehydrogenative-coupling method is developed to react benzoxazin-2-one derivatives with various indoles. As a result, combined use of ball milling and Fe( ii ) catalysis leads to rapid coupling of 1,4-benzoxazinones with derivatives of indole. Under the conditions, derivatives of 1 couple with various indoles at room temperature to produce good yields of
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Organic electrochemistry: Synthesis and functionalization of β-lactams in the twenty-first century Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Martina Bortolami, Isabella Chiarotto, Leonardo Mattiello, Rita Petrucci, Daniele Rocco, Fabrizio Vetica, Marta Feroci
Organic electrochemistry is a technique that allows for the heterogeneous redox reactions avoiding both the use of stoichiometric amounts of redox reagents and the resulting formation of stoichiometric by-products. In fact, the redox reagent in these reactions is the electron, which is naturally eco-friendly and produces no side compounds. It is therefore quite obvious that electrochemistry can be
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Some applications of deep eutectic solvents in alkylation of heterocyclic compounds: A review of the past 10 years Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Maja Molnar, Melita Lončarić, Martina Jakovljević, Mario Komar, Mirjana Lončar
This mini-review encapsulates the latest findings (past 10 years) in the field of the deep eutectic solvents (DESs) application in the alkylation/arylation of different heterocyclic compounds. These solvents have been developed to fulfill the green chemistry concept demands and have been proven excellent for the application in various fields. This review describes their application in different types
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One-pot synthesis of benzofurans via heteroannulation of benzoquinones Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Maryam Pirouz, M. Saeed Abaee, Pernille Harris, Mohammad M. Mojtahedi
Three different reactions were explored leading to the synthesis of various benzofurans. All reactions took place under AcOH catalysis in a one-pot manner. As a result, benzoquinone derivatives underwent heteroannulation with either itself or cyclohexanones to produce furanylidene-benzofuran or benzofuran structures, respectively.
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Molecular, Electronic, Nonlinear Optical and Spectroscopic Analysis of Heterocyclic 3-Substituted-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones: Experiment and DFT Calculations Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Murat Beytur, Ihsan Avinca
In the present study, 3- p -methoxybenzyl/ m -chlorobenzyl/phenyl-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1 H -1,2,4-triazol-5-ones were obtained from the reaction between 3-methylthiophene-2-carbaldehyde and three different 4-amino-(3- p -methoxybenzyl/ m -chlorobenzyl/phenyl)-4,5-dihydro-1 H -1,2,4-triazole-5-ones. In order to compare experimental and theoretical values, the geometric parameter
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Lewis acid / Base-free Strategy for the Synthesis of 2-Arylthio and Selenyl Benzothiazole / Thiazole and Imidazole Heterocycl. Commun. (IF 2.3) Pub Date : 2021-01-01 Guniganti Balakishan, Gullapalli Kumaraswamy, Vykunthapu Narayanarao, Pagilla Shankaraiah
A Cu(II)-catalyzed Csp 2 -Se and Csp 2 -Sulfur bond formation was achieved with moderate to good yields without the aid of Lewis acid and base. The reaction is compatible with a wide range of heterocycles such as benzothiazole, thiazole, and imidazole. Also, this typical protocol is found to be active in thio-selenation via S-H activation. Additionally, we proposed a plausible mechanistic pathway involving
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Synthesis and Activity of New Schiff Bases of Furocoumarin Heterocycl. Commun. (IF 2.3) Pub Date : 2020-12-31 Huijun Xie, Chao Niu, Zeyang Chao, Nuramina Mamat, Haji Akber Aisa
Abstract Furocoumarins, such as 8-MOP, are the most common medications used to relieve the symptoms of vitiligo clinically. Some furocoumarins also showed excellent performance in an anti-bacterial assay. This paper describes the synthesis of a series of novel Schiff bases (6a-6k), and their promotion in melanogenesis and anti-bacterial properties were studied in vitro. The pigment production of B16
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Visible light mediated aerobic oxidative hydroxylation of 2-oxindole-3-carboxylate esters: an alternative approach to 3-hydroxy-2-oxindoles Heterocycl. Commun. (IF 2.3) Pub Date : 2020-11-26 Jinge Wang, Siyitemer Osman, Xinjiang Lu, Junyi Chen, Xu-Dong Xia
Abstract A convenient aerobic oxidative hydroxylation of 3-substituted oxindoles under mild reaction conditions is described herein. This process was accomplished by the activation of molecular oxygen in the air in the presence of a photocatalyst under the irradiation of visible light. The desired product was delivered in up to 89% yield without the addition of base or stoichiometric oxidant.
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Synthesis and Biological Evaluation of Benzodioxole Derivatives as Potential Anticancer and Antioxidant agents Heterocycl. Commun. (IF 2.3) Pub Date : 2020-11-26 Mohammed Hawash, Ahmad M Eid, Nidal Jaradat, Murad Abualhasan, Johnny Amer, Abdel Naser Zaid, Saja Draghmeh, Donia Daraghmeh, Haifa Daraghmeh, Tahrir Shtayeh, Hadeel Sawaftah, Ahmed Mousa
Abstract a series of benzodioxole compounds were synthesized and evaluated for their cytotoxic activity against cervical (Hela), colorectal (Caco-2), and liver (Hep3B) cancer cell lines. Compounds 5a, 5b, 6a, 6b, 7a and 7b showed very weak or negligible anticancer activity with IC50 3.94-9.12 mM. On the contrary, carboxamide containing compounds 2a and 2b showed anticancer activity. Both 2a and 2b
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Synthesis and optical characterization of bipod carbazole derivatives Heterocycl. Commun. (IF 2.3) Pub Date : 2020-10-18 Baki Çiçek, Merve Çağlı, Remziye Tülek, Ali Teke
Abstract In this study, some new biscarbazole derivatives were synthesized for the purpose of being used in OLED technologies and related areas. The following compounds: {1,2-bis(2-(3,6-diphenyl-9H-carbazole-9-yl) ethoxy)ethane (C-1), bis[2-(2-(3,6- diphenyl-9H-carbazole-9-yl) ethoxy)etyl]ether (C-2), bis[2-(2-(3,6-di(naphthalene-1-yl)-9H-carbazol-9-yl)ethoxy)etyl]ether (C-3) and bis [2-(2-(3,6-di
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Design, Synthesis and Study of Antibacterial and Antitubercular Activity of Quinoline Hydrazone Hybrids Heterocycl. Commun. (IF 2.3) Pub Date : 2020-10-15 Shruthi T G, Sangeetha Subramanian, Sumesh Eswaran
Abstract Emerging bacterial resistance is causing widespread problems for the treatment of various infections. Therefore, the search for antimicrobials is a never-ending task. Hydrazones and quinolines possess a wide variety of biological activities. Herewith, eleven quinoline hydrazone derivatives have been designed, synthesized, characterized and evaluated for their antibacterial activity and antitubercular
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Fluorescence properties in different solvents and synthesis of axially substituted silicon phthalocyanine bearing bis-4-tritylphenoxy units Heterocycl. Commun. (IF 2.3) Pub Date : 2020-10-15 Mehmet Salih Ağırtaş
Abstract In this present study, a new axially bis-4-tritylphenoxy substituted silicon phthalocyanine compound was synthesized and characterized using infrared, mass, electronic absorption and nuclear magnetic resonance spectroscopy. Fluorescence and absorption spectra studies of the disubstituted silicon phthalocyanine complex were conducted on the chloroform, dimethyl formamide, dimethyl sulfoxide
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Some topological indices of dendrimers determined by their Banhatti polynomials Heterocycl. Commun. (IF 2.3) Pub Date : 2020-10-02 Zheng-Qing Chu, Muhammad Salman, Asia Munir, Imran Khalid, Masood Ur Rehman, Jia-Bao Liu, Faisal Ali
Abstract Several properties of chemical compounds in a molecular structure can be determined with the aid of mathematical languages provided by various types of topological indices. In this paper, we consider eight dendrimer structures in the context of valency based topological indices. We define four Banhatti polynomials for general (molecular) graphs, and compute them for underline dendrimers. We
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Synthesis, Characterization, and Antioxidant Activity of Some 2-Methoxyphenols derivatives Heterocycl. Commun. (IF 2.3) Pub Date : 2020-09-27 Shaikha S. AlNeyadi, Naheed Amer, Tony G. Thomas, Ruba Al Ajeil, Priya Breitener, N Munawar
Abstract Oxidative stress is a causative factor in the pathophysiology of numerous diseases, such as diabetes, atherosclerosis, cancer, and neurodegenerative and cardiovascular diseases. Therapeutic antioxidants are promising candidates for preventing and treating conditions in which oxidative stress is a contributing factor. In this study, we report the design, synthesis and antioxidant activity of
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Isatin-3-thiosemicarbazone as Chromogenic Sensor for the Selective Detection of Fluoride Anion Heterocycl. Commun. (IF 2.3) Pub Date : 2020-09-22 Safia Rasheed, Mukhtiar Ahmed, Muhammad Faisal, Muhammad Moazzam Naseer
Abstract In this study, we describe the anion recognition ability of isatin-3-thiosemicarbazone 2, which contains two different anion recognition units i.e. isatin NH and the thiourea moiety. Both have the ability to act as proton donors. Most importantly, a significant colour change of 2 was observed (from light yellow to reddish orange) in organic medium only after the addition of the F– anion. No
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Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- and 5-acetoxyalkanethioamide analogues Heterocycl. Commun. (IF 2.3) Pub Date : 2020-06-18 Yasutaka Shimotori, Masayuki Hoshi, Narihito Ogawa, Tetsuo Miyakoshi, Taisei Kanamoto
Abstract 5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial
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Synthesis and biological evaluation of novel 4-oxo-5-cyano thiouracil derivatives as SecA inhibitors Heterocycl. Commun. (IF 2.3) Pub Date : 2020-05-17 Fante Bamba, Jinshan Jin, Phang C. Tai, Binghe Wang
Abstract The continuous emergence of drug-resistant strains of bacteria poses an urgent risk to human health and dictates the need for new antimicrobials. Along this line, we have been working on developing inhibitors of SecA, a key component of the bacterial Sec-dependent secretion machinery. Herein, we describe the synthesis and antimicrobial evaluation of 6-oxo-1,6-dihydropyrimidine-5-carbonitrile
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Synthesis and antiproliferative activities of polymethoxyflavones aminoalkyl and amino acid derivatives Heterocycl. Commun. (IF 2.3) Pub Date : 2020-04-28 Li-qiong Ran, Xue-li Li, Man-hui Liu, Qiu-an Wang
Abstract Twelve novel aminoalkyl derivatives 3a-3f, 4a-4f and four novel amino acid derivatives 5a, 5b, 6a and 6b of polymethoxyflavones 1 and 2 were synthesized through regioselective demethylation, etherification, amination, EDCl-mediated amide condensation and alkaline hydrolysis, using tangeretin and nobiletin as starting materials. Their antiproliferative activities against four different human
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Synthesis and characterization of novel biological tetracoumarin derivatives bearing ether moieties Heterocycl. Commun. (IF 2.3) Pub Date : 2020-04-03 Soheila Asadpour Behzadi, Enayatollah Sheikhhosseini, Sayed Ali Ahmadi, Dadkhoda Ghazanfari, Mohammadreza Akhgar
Abstract A series of novel tetracoumarin derivatives (3a-f) were prepared using the reaction of ether functionalized dibenzaldehyde with 4-hydroxycoumarin in the presence of sodium acetate. The structure of compounds was validated by IR, NMR, and CHN analyzes. Antimicrobial (antibacterial and antifungal) activity was studied on the basis of the minimum bactericidal concentration, minimum inhibitory
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Coumarin sulfonamide derivatives: An emerging class of therapeutic agents Heterocycl. Commun. (IF 2.3) Pub Date : 2020-04-03 Ali Irfan, Laila Rubab, Mishbah Ur Rehman, Rukhsana Anjum, Sami Ullah, Mahwish Marjana, Saba Qadeer, Sadia Sana
Abstract Coumarin sulfonamide is a heterocyclic pharmacophore and an important structural motif which is a core and integral part of different therapeutic scaffolds and analogues. Coumarin sulfonamides are privileged and pivotal templates which have a broad spectrum of applications in the fields of medicine, pharmacology and pharmaceutics. Coumarin sulfonamide exhibited versatile and myriad biomedical
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Ball-Type Dioxy-o-Carborane Bridged Cobaltphthalocyanine: Synthesis, Characterization and DFT Studies For Dye-Sensitized Solar Cells as Photosensitizer Heterocycl. Commun. (IF 2.3) Pub Date : 2020-03-17 Sevil Şener
Abstract The synthesis and spectroscopic characterization of an innovative ball-type cobalt metallophthalocyanine 4, bridged by four 1,2-bis(2-hydroxymethyl)-O-carborane (HMOC) 1 units, has been achieved. The synthesized compound 4 was characterized structurally and electronically using elemental analysis, UV-Vis absorption spectroscopy, FT-IR spectroscopy, MALDI-TOF mass spectrometry, EPR spectroscopy
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Isatin as a simple, highly selective and sensitive colorimetric sensor for fluoride anion Heterocycl. Commun. (IF 2.3) Pub Date : 2020-03-17 Azeem Haider, Mukhtiar Ahmed, Muhammad Faisal, Muhammad Moazzam Naseer
Abstract Herein, we report the fluoride anion sensing properties of a commercially available and inexpensive organic compound, isatin, which is found to be a highly selective and sensitive sensor. In naked-eye experiments, by addition of fluoride anions, isatin shows a dramatic color change from pale yellow to violet at room temperature, while the addition of other anions, i.e. C l − , $\mathrm{Cl}^-
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Reactivity of 1-allylsilatrane in ruthenium-catalyzed silylative coupling with olefins – mechanistic considerations Heterocycl. Commun. (IF 2.3) Pub Date : 2020-03-10 Bogna Sztorch, Dawid Frąckowiak, Bogdan Marciniec
Abstract We have developed a new effective route for obtaining (E)-vinyl-substituted silatranes via ruthenium-catalyzed silylative coupling of 1-allylsilatrane with olefins. Experimental research allowed us also to propose the mechanism of the process based on stoichiometric reactions.
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A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H )-dione and Octahydroacridin-10(1H )-yl)thiourea Derivatives: Inter- and Intramolecular Aza-Michael addition Heterocycl. Commun. (IF 2.3) Pub Date : 2020-03-10 Nader Noroozi Pesyan, Narmin Akhteh, Hana Batmani, Barış Anıl, Ertan Şahin
Abstract An easy and convenient technique for the one-pot synthesis of novel compounds of hexahydroacridine-1,8(2H,5H)-dione and octahydroacridin-10(1H)-yl) thiourea derivatives has been developed by the reaction of the octahydro-1H-xanthenes with hydroxylamine hydrochloride and thiosemicarbazide in ethylene glycol, which is a green solvent, under mild reaction conditions. IR, 1H NMR, 13C NMR spectrometry
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Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents Heterocycl. Commun. (IF 2.3) Pub Date : 2020-03-10 Ulviye Acar Çevik, Derya Osmaniye, Serkan Levent, Begüm Nurpelin Sağlik, Betül Kaya Çavuşoğlu, Yusuf Özkay, Zafer Asım Kaplancikl
Abstract Cancer is one of the most common causes of death in the world. Despite the importance of combating cancer in healthcare systems and research centers, toxicity in normal tissues and the low efficiency of anticancer drugs are major problems in chemotherapy. Nowadays the aim of many medical research projects is to discover new safer and more effective anticancer agents. 1,3,4-Thiadiazole compounds
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The oxidative coupling between benzaldehyde derivatives and phenylacetylene catalyzed by rhodium complexes via C-H bond activation Heterocycl. Commun. (IF 2.3) Pub Date : 2020-03-08 Xinyi Zhao, Hongge Jia, Qingji Wang, Heming Song, Yanan Tang, Liqun Ma, Yongqiang Shi, Guoxing Yang, Yazhen Wang, Yu Zang, Shuangping Xu
Abstract This paper reports the use of rhodium (Rh) catalysts for the oxidative coupling reaction between phenylacetylene and benzaldehyde derivatives via C-H bond activation. These reactions were catalyzed by Rh(l-amino acid)(cod) (the l-amino acid is l-phenylalanine, l-valine or l-proline; cod is 1,5-cyclooctadiene) to obtain chromones in 12.7–88.3% yield. These new Rh catalysts have excellent activity
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Synthesis of 2-aryl-benzothiazoles via Ni-catalyzed coupling of benzothiazoles and aryl sulfamates Heterocycl. Commun. (IF 2.3) Pub Date : 2020-02-28 Xiaofeng Yu, Zhen Zhang, Renyuan Song, Liping Gou, Guangrong Wang
Abstract 2-Aryl-benzothiazoles have been successfully synthesized via a simple coupling reaction between benzothiazoles and aryl sulfamates using a nickel catalyst. The nickel catalyst is inexpensive, reusable and commercially available. In addition, the use of highly expensive palladium catalysts and unstable raw materials has been avoided. 2-Aryl-benzothiazoles bearing various substituents on the
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Facile Synthesis of Spiro[cyclohexane-1,3’-indoline]-2,2’-diones Heterocycl. Commun. (IF 2.3) Pub Date : 2019-12-31 Shin-taro Katayama, Hiroshi Nishino
Abstract Spiro[cyclohexane-1,3’-indoline]-2,2’-diones were easily prepared in good to high yields by the oxidation of N-aryl-N-methyl-2-oxocyclohexane-1-carboxamides in one pot with a short reaction time. The spiroindolinediones could be important for the total synthesis of natural products.
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Synthesis and AChE inhibitory activity of N-glycosyl benzofuran derivatives Heterocycl. Commun. (IF 2.3) Pub Date : 2019-12-31 Yu-Ran Wu, Shu-Ting Ren, Lei Wang, Xiu-Jian Liu, You-Xian Wang, Shu-Hao Liu, Wei-Wei Liu, Da-Hua Shi, Zhi-Ling Cao
Abstract Six N-glycosyl benzofuran derivatives were synthesized by the catalysis of organic bases and condensation agents. The benzofuran derivatives were obtained by the reaction of various salicylaldehydes in acetone, and then hydrolyzed to the corresponding carboxylic acids. Finally, the target compounds were synthesized by acylation and the reaction conditions were optimized. The acetylcholinesterase
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A Green Synthesis and Antibacterial Activity of N-Arylsulfonylhydrazone Compounds Heterocycl. Commun. (IF 2.3) Pub Date : 2019-12-31 Qian Yang, Wangwang Hao, Yangqing He, Qian Zhang, Xiaojiao Yu, Yaobing Hua
Abstract A green method has been developed for the synthesis of N-arylsulfonylhydrazones via a simple grindstone procedure. By grinding mixtures of benzensulfonyl hydrazides and a series of aryl aldehydes or ketones in the mortar using L-tyrosine as catalyst, 24 N-arylsulfonylhydrazones were synthesized in a few minutes with high yield. All compounds were screened for their antibacterial activities
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Naphthalene substituted benzo[c]coumarins: Synthesis, characterization and evaluation of antibacterial activity and cytotoxicity Heterocycl. Commun. (IF 2.3) Pub Date : 2019-12-31 Mrugesh Patel, Kaushal Patel
Abstract Novel congeners of naphthalene substituted benzo[c]coumarins (2a-f) were synthesized by reaction of various 3-coumarinoyl methyl pyridinium bromide salts (1a-d) with a selected set of acetyl naphthalene in the presence of sodium acetate in refluxing glacial acetic acid. Structures of the synthesized compounds were confirmed by elemental analysis and by various spectroscopic techniques such
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[DMImd-DMP]: A highly efficient and reusable catalyst for the synthesis of 4H-benzo[b]pyran derivatives Heterocycl. Commun. (IF 2.3) Pub Date : 2019-12-31 Mohamed Abdenour Redouane, Naima Khiri-Meribout, Saida Benzerka, Abdelmadjid Debache
Abstract A series of substituted 4H-pyrans derivatives were synthesized by a one-pot, multi-component reaction of aromatic aldehydes, malononitrile, and pyrazolone derivatives or active methylene carbonyl compounds such as dimedone, in the presence of 1,3-dimethyl imidazolium dimethyl phosphate [DMImd-DMP] as a catalyst in aqueous ethanol. Recyclability of the catalyst, high yields, simple product
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Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives Heterocycl. Commun. (IF 2.3) Pub Date : 2019-12-19 Ling Lin, Xiaoguang Chen, Junhao Zhao, Suitao Lin, Guojian Ma, Xiaojian Liao, Pengju Feng
Abstract This paper discloses an efficient one-pot protocol to convert easily accessible 3-nitropyridines to 3-acetamidopyridin-2-yl 4-methylbenzenesulfonate derivatives which are core structures of many pharmaceutical molecules. The strategy successfully combined a three-step reaction in one pot via progressively adding different reactants at rt. The reaction displays good functional group tolerance
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Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents Heterocycl. Commun. (IF 2.3) Pub Date : 2019-11-28 Wei Zhou, Qingwei Xiao, Yuanyuan Chang, Qifa Liu, Xiaohao Zang, Mengmeng Hu, Xi Zeng, Zhiyun Du, Guifa Zhong
Abstract Herein is described a diastereoselective Michael addition of Grignard reagents to α, β- unsaturated diethyl malonates incorporated with a 2-oxazolidone chiral auxiliary. The catalyst-free Michael addition proceeds with good chemical efficiency and excellent stereoselectivity; and it provides new thoughts to the asymmetric synthesis of β-substituted β3 amino acid derivatives.
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Cytotoxic and antimicrobial activities of some novel heterocycles employing 6-(1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile Heterocycl. Commun. (IF 2.3) Pub Date : 2019-11-28 Sayed K. Ramadan, Eman A. E. El-Helw, Hanan A. Sallam
Abstract A pyrimidinethione derivative namely, 6-(1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile, was readily synthesized and reacted with carbon electrophiles in an attempt to synthesize selected fused heterocycles. The reactivity of 6-(1,3-diphenyl-1H-pyrazol-4-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile was investigated towards selected
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Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides Heterocycl. Commun. (IF 2.3) Pub Date : 2019-11-28 Pavlo V. Zadorozhnii, Ihor O. Pokotylo, Vadym V. Kiselev, Aleksandr V. Kharchenko, Oxana V. Okhtina
Abstract Based on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides. The reaction was carried out in boiling glacial acetic
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Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case Heterocycl. Commun. (IF 2.3) Pub Date : 2019-11-28 Daniel Canseco-González, José Luis Rodríguez de la O, José Enrique Herbert-Pucheta
Abstract Copper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) click chemistry robustness has been demonstrated over recent years to produce 1,2,3-triazoles with excellent yields at mild conditions with simple purification methods. However, the consequences of having copper paramagnetic traces in final products, which complicate spectroscopic assignments and can produce inaccurate conclusions, has been
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Synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction Heterocycl. Commun. (IF 2.3) Pub Date : 2019-11-28 Mohammad Bakherad, Ali Keivanloo, Amir H. Amin, Amir Farkhondeh
Abstract An efficient method has been developed for the synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction in ethanol at 50°C. A broad range of aromatic azides were successfully reacted with n-propynylated benzimidazole via copper-catalyzed azide-alkyne cycloaddition reactions in the absence of a ligand. This method offers many advantages including short reaction
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Synthesis and fungicidal activities of perfluoropropan-2-yl-based novel quinoline derivatives Heterocycl. Commun. (IF 2.3) Pub Date : 2019-05-31 Zai Zhang, Minhua Liu, Weidong Liu, Jun Xiang, Jianming Li, Zhong Li, Xingping Liu, Mingzhi Huang, Aiping Liu, Xingliang Zheng
Abstract A series of novel perfluoropropan-2-yl-based quinoline derivatives was designed and synthesized utilizing tebufloquin as the lead compound. The structures of all the newly synthesized compounds were confirmed by spectroscopic data 1HNMR, MS and elemental analysis. The results of bioassay indicated that these compounds exhibited potent fungicidal activities against Erysiphe graminis. Especially
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The first in situ synthesis of 1,3-dioxan-5-one derivatives and their direct use in Claisen-Schmidt reactions Heterocycl. Commun. (IF 2.3) Pub Date : 2019-05-31 M. Javad Poursharifi, Mohammad M. Mojtahedi, M. Saeed Abaee, Mohammad M. Hashemi
Abstract A method is developed for in situ generation of 1,3-dioxan-5-one derivatives 2. These compounds are simple precursors for accessing carbohydrate structures and previously had to be produced via stepwise procedures using excessive amounts of reagents. In the present work, three different derivatives of 2 were synthesized via the reaction of trialkoxyalkanes with dihydroxyacetone dimer 1 in