作为潜在抗抑郁药和促智药的异烟碱腙的希夫碱和 2-氮杂环丁酮的合成和生物学评价,Arabian Journal of Chemistry

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作为潜在抗抑郁药和促智药的异烟碱腙的希夫碱和 2-氮杂环丁酮的合成和生物学评价
Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2016-09-01 , DOI: 10.1016/j.arabjc.2011.02.015
Asha B. Thomas , Rabindra K. Nanda , Lata P. Kothapalli , Sunil C. Hamane

摘要 N'-[(1Z)-(取代芳香族)亚甲基]吡啶-4-碳酰肼(3a-k)和N-[3-氯-2-(取代芳香族)-4-氧代氮杂环丁烷-描述了 1-yl]pyridine-4-carboxamides (5a-k)。2-氮杂环丁酮的合成是通过搅拌和超声处理的新方法进行的，包括适当的希夫碱 (3a-k) 与氯乙酰氯的环缩合，然后在分子筛的存在下加入三乙胺。研究了化合物的抗抑郁活性，化合物 N'-[(1Z)-(2,5-二甲氧基苯基)亚甲基]吡啶-4-碳酰肼 (3k) 和 N-[3-氯-2-(2,5-二甲氧基苯基)-4-氧代氮杂环丁烷-1-基]吡啶-4-甲酰胺(5k)在芳环上具有2,5-二甲氧基取代表现出最高的抗抑郁活性。在小鼠高架十字迷宫试验和被动回避试验中评估促智活性 N'-[(1Z)-(4-nitrophenyl)methylidene]pyridine-4-carbohydrazide (3d) 和 N-[3-chloro-2 -(4-硝基苯基)-4-oxoazetidin-1-yl]pyridine-4-carboxamide (5d) 与芳环上的对硝基取代表现出最高的活性。所有合成的希夫碱和氮杂环丁酮类似物均以剂量依赖性方式表现出抗抑郁和促智活性。结果证实了这样一个事实，即 2-氮杂环丁酮骨架具有作为 CNS 活性剂的潜力，可以探索开发更有效、更安全的 CNS 活性剂用于治疗用途。

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Synthesis and biological evaluation of Schiff’s bases and 2-azetidinones of isonocotinyl hydrazone as potential antidepressant and nootropic agents

Abstract The synthesis and pharmacological activity of N′-[(1Z)-(substituted aromatic) methylidene] pyridine-4-carbohydrazides (3a–k) and N-[3-chloro-2-(substituted aromatic)-4-oxoazetidin-1-yl]pyridine-4-carboxamides (5a–k) are described. Synthesis of 2-azetidinones was performed by novel methods of stirring and sonication involving the cyclocondensation of the appropriate Schiff’s bases (3a–k) with chloroacetyl chloride, followed by the addition of triethyl amine in the presence of molecular sieves. The compounds were investigated for their antidepressant activity, compounds N′-[(1Z)-(2,5-dimethoxyphenyl)methylidene]pyridine-4-carbohydrazide (3k) and N-[3-chloro-2-(2,5-dimethoxyphenyl)-4-oxoazetidin-1-yl]pyridine-4-carboxamide (5k) with 2,5-dimethoxy substitution on the aryl ring exhibited the highest antidepressant activity. In the elevated plus maze test and passive avoidance test in mice for the evaluation of nootropic activity N′-[(1Z)-(4-nitrophenyl)methylidene]pyridine-4-carbohydrazide (3d) and N-[3-chloro-2-(4-nitrophenyl)-4-oxoazetidin-1-yl]pyridine-4-carboxamide (5d) with para nitro substitution on the aryl ring exhibited the highest activity. All synthesised Schiff’s bases and azetidinone analogues exhibited antidepressant and nootropic activities in a dose dependant manner. The results confirmed the fact that the 2-azetidinone skeleton has potential as a CNS active agent and can be explored for the development of more potent and safe CNS active agents for therapeutic use.

更新日期：2016-09-01

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