Microwave‐assisted synthesis of triazole derivatives conjugated with piperidine as new anti‐enzymatic agents,Journal of Heterocyclic Chemistry

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Microwave‐assisted synthesis of triazole derivatives conjugated with piperidine as new anti‐enzymatic agents
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2019-12-29 , DOI: 10.1002/jhet.3875
Naeem A. Virk ₁ , Aziz‐ur‐ Rehman ₁ , Muhammad A. Abbasi ₁ , Sabahat Z. Siddiqui ₁ , Javed Iqbal ₂ , Shahid Rasool ₁ , Shafi U. Khan ₃ , Thet T. Htar ₃ , Hira Khalid ₄ , Sabina J. Laulloo ₅ , Syed A. Ali Shah _{6,

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Affiliation

The current study was aimed for the study of piperidine‐based triazole compounds for their biological potential against various enzymes. A novel library of compounds, 9a‐r, having piperidine, 1,2,4‐triazole, and propanamides was synthesized through consecutive steps including the formation of sulfonamide, hydrazide, 1,2,4‐triazole, and thio‐ether. Initially, 4‐methoxybenzenesulfonyl chloride (1) and ethyl isonipecotate (2) were utilized to develop ethyl 1‐(4‐methoxyphenylsulfonyl)‐4‐piperidinecarboxylate (3). The product 3 was converted into respective hydrazide (4) which was further cyclized into 1,2,4‐triazole (5) nucleus. A series of propanamides, 8a‐r, were synthesized from different amines, 6a‐r. These electrophiles, 8a‐r, were reacted with compound 5 under conventional and microwave‐assisted protocols to acquire the library of hybrids, 9a‐r. The structural confirmations were availed by ¹H‐NMR, ¹³C‐NMR, and IR techniques. The whole series was evaluated for biological potential against acetylcholinesterase (AChE) and α‐glucosidase enzymes. The biological evaluation ranges low to high in potential for different compounds based on the structural variations of synthesized compounds. Almost all the compounds remained active against both the enzymes except a few ones. The bovine serum albumin (BSA) binding study demonstrated the flow of drug in the body, and the docking study explained the interactions responsible for active behavior of synthesized compounds.

中文翻译：

微波辅助合成与哌啶共轭的三唑衍生物作为新型抗酶剂

当前的研究旨在研究基于哌啶的三唑化合物对各种酶的生物学潜力。通过连续步骤（包括形成磺酰胺，酰肼，1,2,4-三唑和硫醚），合成了具有哌啶，1,2,4-三唑和丙酰胺的新型化合物9a-r。最初，使用4-甲氧基苯磺酰氯（1）和异二十二碳六烯酸乙酯（2）来开发1-（4-甲氧基苯基磺酰基）-4-哌啶甲酸乙酯（3）。产物3分别转化为酰肼（4），然后进一步环化成1,2,4-三唑（5）核。一系列的丙酰胺，8a-r是由不同的胺6a-r合成的。这些亲电子体8a-r在常规和微波辅助方案下与化合物5反应，获得了杂合体9a-r库。通过¹ H-NMR，¹³获得结构确认C-NMR和IR技术。评估了整个系列针对乙酰胆碱酯酶（AChE）和α-葡萄糖苷酶的生物潜力。根据合成化合物的结构变化，对不同化合物进行生物学评估的潜力范围从低到高。除少数几种酶外，几乎所有化合物都对两种酶保持活性。牛血清白蛋白（BSA）结合研究证明了药物在体内的流动，对接研究解释了负责合成化合物活性行为的相互作用。

更新日期：2019-12-30

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