Abstract
A novel series of bis(sulfanediyl)bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) which are linked to benzene, pyridine, or thieno[4,5-d]thiophene cores were prepared to via multicomponent reaction of bis(sulfanediyl))bis(6-aminopyrimidin-4(1H)-ones) with two equivalents of both dimedone and the appropriate aromatic aldehyde. The target molecules were alternatively prepared via the bis-alkylation reactions of the appropriate 5-aryl-2-thioxohexahydropyrimido[4,5-b]quinoline-4,6-dione with the corresponding dibromo compounds.
Graphic abstract
Similar content being viewed by others
References
Candeias NR, Montalbano F, Cal PMSD, Gois PMP (2010) Chem Rev 110:6169
Isambert N, del Duque MS, Plaquevent J-C, Génisson Y, Rodriguez J, Constantieux T (2011) Chem Soc Rev 40:1347
Shiri M (2012) Chem Rev 112:3508
Dömling A, Wang W, Wang K (2012) Chem Rev 112:3083
Brauch S, van Berkel SS, Westermann B (2013) Chem Soc Rev 42:4948
Chen MN, Mo LP, Cui ZS, Zhang ZH (2019) Curr Opin Green Sustain Chem 15:27
Zhang M, Liu YH, Shang ZR, Hu HC, Zhang ZH (2017) Catal Commun 88:39
Choi SJ, Cho JH, Im I, Lee SD, Jang JY, Oh YM, Jung YK, Jeon ES, Kim YC (2010) Eur J Med Chem 45:2578
Safak C, Simsek R (2006) Mini Rev Med Chem 6:747
Wachter GA, Davis MC, Martin AR, Franzblau SG (1998) J Med Chem 41:2436
Wollmann J, Baumert C, Erlenkamp G, Sippl W, Hilgeroth A (2008) ChemBioChem 9:874
Tusell JM, Barron S, Serratosa J (1993) Brain Res 622:99
Murthy YLN, Rajack A, Ramji MT, Babu JJ, Praveen C, Lakshmic KA (2012) Bioorg Med Chem Lett 22:6016
Carosati E, Mannhold R, Wahl P, Hansen JB, Fremming T, Zamora I, Cianchetta G, Baroni M (2007) J Med Chem 50:2117
Joshi AA, Viswanathan CL (2006) Bioorg Med Chem Lett 16:2613
Muruganantham N, Sivakumar R, Anbalagan N, Gunasekaran V, Leonard JT (2004) Biol Pharm Bull 27:1683
Narender P, Srinivas U, Ravinder M, Rao BA, Ramesh C, Harakishore K, Gangadasu B, Murthy USN, Rao VJ (2006) Bioorg Med Chem 14:4600
Ridley RG (2002) Nature 415:686
Tsotinis A, Vlachou M, Zouroudis S, Jeney A, Timár F, Thurston DE, Roussakis C (2005) Lett Drug Des Discov 2:189
Kolocouris A, Dimas K, Pannecouque C, Witvrouw M, Foscolos GB, Stamatiou G, Fytas G, Zoidis G, Kolocouris N, Andrei G, Snoeck R, De Clercq E (2002) Bioorg Med Chem Lett 12:723
Quintela J, Peinador C, Botana L, Estévez M, Riguera R (1997) Bioorg Med Chem 5:1543
Girgis AS, Hosni HM, Ahmed-Farag IS (2003) Z Naturforsch B 58:678
Amr AE, Abdulla MM (2006) Bioorg Med Chem 14:4341
Son J-K, Zhao L-X, Basnet A, Thapa P, Karki R, Na Y, Jahng Y, Jeong TC, Jeong B-S, Lee C-S, Lee E-S (2008) Eur J Med Chem 43:675
Xie F, Zhao H, Zhao L, Lou L, Hu Y (2009) Bioorg Med Chem Lett 19:275
Pathak V, Maurya HK, Sharma S, Srivastava KK, Gupta A (2014) Bioorg Med Chem Lett 24:2892
Abdelgawad MA, Bakr RB, Azouz AA (2018) Bioorg Chem 77:339
Diab HM, Salem ME, Abdelhamid IA, Elwahy AHM (2021) ARKIVOC 2021:329
Cordeu L, Cubedo E, Bandrés E, Rebollo A, Sáenz X, Chozas H, Domínguez MV, Echeverría M, Mendivil B, Sanmartin C, Palop JA (2007) Bioorg Med Chem 15:1659
Alqasoumi SI, Al-Taweel AM, Alafeefy AM, Noaman E, Ghorab MM (2010) Eur J Med Chem 45:738
Insuasty B, Becerra D, Quiroga J, Abonia R, Nogueras M, Cobo J (2013) J Heterocycl Chem 50:506
Ghorab MM, Ragab F, Heiba HI, Arafa RK, El-Hossary EM (2010) Eur J Med Chem 45:3677
Selvi ST, Nadaraj V, Mohan S, Sasi R, Hema M (2006) Bioorg Med Chem 14:3896
El-Gazzar ABA, Hafez HN, Nawwar GAM (2009) Eur J Med Chem 44:1427
Rajanarendar E, Reddy MN, Krishna SR, Murthy KR, Reddy YN, Rajam MV (2012) Eur J Med Chem 55:273
El-Gazzar ARBA, El-Enany MM, Mahmoud MN (2008) Bioorg Med Chem 16:3261
Muregi FW, Ishih A (2009) Drug Dev Res 71:20
Singh K, Kaur H, Smith P, De Kock C, Chibale K, Balzarini J (2014) J Med Chem 57:435
Viegas-Junior C, Barreiro EJ, Fraga CAM (2007) Curr Med Chem 14:1829
Abdella AM, Mohamed MF, Mohamed AF, Elwahy AHM, Abdelhamid IA (2018) J Heterocycl Chem 55:498
Abdelhamid IA, Darwish ES, Nasra MA, Abdel-Gallil FM, Fleita DH (2010) Synthesis 2010:1107
Elnagdi MH, Al-Awadi NA, Abdelhamid IA (2009) Adv Heterocycl Chem 97:1
Al-Awadi NA, Ibrahim MR, Abdelhamid IA, Elnagdi MH (2008) Tetrahedron 64:8202
Abdelmoniem AM, Salaheldin TA, Abdelhamid IA, Elwahy AHM (2017) J Heterocycl Chem 54:2670
Ghozlan SAS, Abdelmoniem AM, Butenschön H, Abdelhamid IA (2015) Tetrahedron 71:1413
Abdella AM, Elwahy AHM, Abdelhamid IA (2016) Curr Org Synth 13:601
Fares IMZ, Mekky AEM, Elwahy AHM, Abdelhamid IA (2020) Synth Commun 50:893
Abdella AM, Abdelmoniem AM, Ibrahim NS, El-Hallouty SM, Abdelhamid IA, Elwahy AHM (2020) Mini Rev Med Chem 20:801
Hawass MAE, Sanad SMH, Elwahy AHM, Abdelhamid IA (2021) Synth Commun 51:1899
Teleb MAM, Hassaneen HM, Abdelhamid IA, Saleh FM (2021) Synth Commun 51:553
Abdelmoniem AM, Abdelrahman MGM, Ghozlan SAS, Elwahy AHM, Abdelhamid IA (2021) Synth Commun 51:1814
Darweesh AF, Abd El-Fatah NA, Abdel-Latif SA, Abdelhamid IA, Elwahy AHM, Salem ME (2021) ARKIVOC 2021:23
Diab HM, Abdelhamid IA, Elwahy AHM (2018) Synlett 29:1627
Diab HM, Salem ME, Elwahy AHM, Abdelhamid IA (2021) Synth Commun 51:2001
Darweesh AF, Salama SK, Abdelhamid IA, Elwahy AHM (2021) J Heterocycl Chem 58:315
Darweesh AF, Salama SK, Abdelhamid IA, Elwahy AHM (2021) Synth Commun 51:471
El-Fatah NAA, Darweesh AF, Mohamed AA, Abdelhamid IA, Elwahy AHM (2017) Monatsh Chem 148:2107
Shaaban MR, Elwahy AHM (2012) J Heterocycl Chem 49:640
Crepaldi P, Cacciari B, Bonache MC, Spalluto G, Varani K, Borea PA, von Kügelgen I, Hoffmann K, Pugliano M, Razzari C, Cattaneo M (2009) Bioorg Med Chem 17:4612
Cheng CC, Lewis LR (1964) J Heterocycl Chem 1:260
Mashraqui SH, Sangvikar YS, Meetsma A (2006) Tetrahedron Lett 47:5599
Sayed OM, Mekky AEM, Farag AM, Elwahy AHM (2014) J Sulfur Chem 36:124
Mashraqui SH, Sangvikar YS, Ghadigaonkar SG, Ashraf M, Meetsma M (2008) Tetrahedron 64:8837
Mekky AEM, Elwahy AHM (2014) J Heterocycl Chem 51:E34
Abdelhamid IA (2009) Synlett 2009:625
Ghozlan SAS, Mohamed MF, Ahmed AG, Shouman SA, Attia YM, Abdelhamid IA (2015) Arch Pharm (Weinheim) 348:113
Abdelmoniem AM, Elwahy AHM, Abdelhamid IA (2016) ARKIVOC iii:304
Abdelhamid IA, Mohamed MH, Abdelmoniem AM, Ghozlan SAS (2009) Tetrahedron 65:10069
Mohamed MF, Abdelmoniem AM, Elwahy AHM, Abdelhamid IA (2018) Curr Cancer Drug Targets 18:372
Abdelmoniem AM, Hassaneen HME, Abdelhamid IA (2016) J Heterocycl Chem 53:2084
Author information
Authors and Affiliations
Corresponding authors
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Diab, H.M., Salem, M.E., Abdelhamid, I.A. et al. Hantzsch-like synthesis of bis(sulfanediyl)bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) linked to arene or heteroarene cores utilizing bis(sulfanediyl)bis(6-aminopyrimidin-4-ones) as precursors. Monatsh Chem 152, 967–976 (2021). https://doi.org/10.1007/s00706-021-02825-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-021-02825-4