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超声辅助一锅四组分合成新型含 5-咪唑并吡唑骨架的 2-氨基-3-氰基吡啶衍生物及其生物播散性。

Ultrasound-assisted one-pot four-component synthesis of novel 2-amino-3-cyanopyridine derivatives bearing 5-imidazopyrazole scaffold and their biological broadcast.

机构信息

Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120, Gujarat, India.

Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120, Gujarat, India.

出版信息

Eur J Med Chem. 2014 Aug 18;83:655-64. doi: 10.1016/j.ejmech.2014.06.071. Epub 2014 Jun 30.

Abstract

An alternative and environmentally caring way for the synthesis of novel 2-amino-3-cyanopyridine derivatives bearing 5-imidazopyrazole nucleus is reported by one-pot four-component cyclocondensation reaction of substituted 5-(1H-imidazol/4-methyl-1-yl)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3a-b), malononitrile (4), ammonium acetate (5) and aromatic (6a-f)/heterocyclic methyl ketones (7a-d) under ultrasonic irradiation. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against a panel of pathogenic stains of bacteria and fungi, in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv stain and in vitro antioxidant activity by ferric-reducing antioxidant power method. Compounds 8e, 8h, 8l, 9c, 9g and 9h exhibited excellent antibacterial activity and compounds 3a, 8k, 9a and 9bshowed moderate antituberculosis activity as compared with the first line drugs. Majority of the compounds showed excellent antioxidant activity. This approaches claimed to be an environment friendly protocol as it afforded numerous advantages i.e. excellent yields, cleaner reaction profile and shorter reaction time.

摘要

报道了一种通过一锅四组分环缩合反应,由取代的 5-(1H-咪唑/4-甲基-1-基)-3-甲基-1-苯基-1H-吡唑-4-甲酰基(3a-b)、丙二腈(4)、乙酸铵(5)和芳基(6a-f)/杂环甲基酮(7a-d)合成新型含 5-咪唑并吡唑核的 2-氨基-3-氰基吡啶衍生物的替代方法,该方法在超声辐射下进行。新合成的化合物进行了体外抗菌活性评估,针对一系列致病性细菌和真菌菌株进行了评估,对结核分枝杆菌 H37Rv 菌株进行了体外抗结核活性评估,并通过铁还原抗氧化能力法进行了体外抗氧化活性评估。化合物 8e、8h、8l、9c、9g 和 9h 表现出优异的抗菌活性,化合物 3a、8k、9a 和 9b 表现出中等的抗结核活性,与一线药物相比。大多数化合物表现出优异的抗氧化活性。该方法声称是一种环保的方案,因为它具有许多优点,即产率高、反应谱更清洁、反应时间更短。

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