Zeolite‐catalyzed synthesis of nicotinyl‐fused indolo‐pyrazoles and evaluation of their activities against Anopheles arabiensis and Lipoxygenase,Journal of Heterocyclic Chemistry

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Zeolite‐catalyzed synthesis of nicotinyl‐fused indolo‐pyrazoles and evaluation of their activities against Anopheles arabiensis and Lipoxygenase
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-11-20 , DOI: 10.1002/jhet.4190
T. R. Makhanya ₁ , R. M. Gengan ₁

Affiliation

A series of nicotyl‐fused indolo‐pyrazoles (NFIPs) were synthesized by a one‐pot multicomponent reaction of aryl aldehydes, isoniazid, and indole in the presence of zeolite as a catalyst. Structures of all the synthesized compounds were established by IR, ¹H‐NMR, ¹³C‐NMR, 2D‐NMR, TOF‐MS, and elemental analysis. The products were obtained in excellent yields and high purity. All 10 compounds were screened for larvicidal and insecticidal properties against Anopheles arabiensis and tested for their lipoxygenase inhibitory activity. Compounds (3‐(3‐hydroxy‐4‐methoxyphenyl)‐2,3‐dihydropyrazolo[4,3‐b]indol‐1(4H)‐yl)(pyridin‐4‐yl)methanone (4i) and (3‐(3‐bromo‐5‐hydroxy‐4‐methoxyphenyl)‐2,3‐dihydropyrazolo[4,3‐b]indol‐1(4H)‐yl)(pyridin‐4‐yl)methanone (4j) displayed highest larvae mortality at a 4 μg/ml dose in 24 h. Compounds (3‐(4‐methoxyphenyl)‐2,3‐dihydropyrazolo[4,3‐b]indol‐1(4H)‐yl)(pyridin‐4‐yl)methanone (4h) and (3‐(3‐hydroxy‐4‐methoxyphenyl)‐2,3‐dihydropyrazolo[4,3‐b]indol‐1(4H)‐yl)(pyridin‐4‐yl)methanone (4i) showed a significant knockdown activity after 24 h with 70% mortality. Furthermore, (3‐(4‐chlorophenyl)‐2,3‐dihydropyrazolo[4,3‐b]indol‐1(4H)‐yl)(pyridin‐4‐yl)methanone (4c) and (3‐(3‐bromo‐5‐hydroxy‐4‐methoxyphenyl)‐2,3‐dihydropyrazolo[4,3‐b]indol‐1(4H)‐yl)(pyridin‐4‐yl)methanone (4j) displayed promising lipoxygenase inhibitory activity with a mortality of 70% and 60%, respectively.

中文翻译：

沸石催化的烟酰胺基吲哚并吡唑类化合物的合成及其对阿拉伯按蚊和脂氧合酶活性的评价

在沸石作为催化剂的情况下，通过芳基醛，异烟肼和吲哚的单锅多组分反应合成了一系列烟酰胺基稠合的吲哚-吡唑（NFIP）。所有合成化合物的结构均通过IR，¹ H-NMR，¹³ C-NMR，2D-NMR，TOF-MS和元素分析确定。以优异的产率和高纯度获得产物。筛选所有10种化合物对阿拉伯按蚊的杀幼虫和杀虫特性，并测试其脂氧合酶抑制活性。化合物（3-（3-羟基-4-甲氧基苯基）-2,3-二氢吡唑并[4,3-b]吲哚-1（4H）-基）（吡啶-4-基）甲酮（4i）和（3-（3-溴-5-羟基-4-甲氧基苯基）-2-，3-二氢吡唑并[4,3-b]吲哚-1（4H）-基）（吡啶-4-基）甲酮（4j ）在24小时内以4μg/ ml的剂量显示出最高的幼虫死亡率。化合物（3-（4-甲氧基苯基）-2,3-二氢吡唑并[4,3-b]吲哚-1（4H）-基）（吡啶-4-基）甲酮（4h）和（3-（3-羟基-4-甲氧基苯基）-2,3-二氢吡唑并[4,3-b]吲哚-1（4H）-基）（吡啶-4-基）甲酮（4i）在24小时后显示出显着的敲低活性，死亡率为70％。此外，（3-（4-氯苯基）-2-，3-二氢吡唑并[4,3-b]吲哚-1（4H）-基）（吡啶-4-基）甲酮（4c）和（3-（3-3-溴-5-羟基-4-甲氧基苯基）-2,3-二氢吡唑并[4,3-b]吲哚-1（4H）-基）（吡啶-4-基）甲酮（4j）显示出有希望的脂氧合酶抑制活性，死亡率分别为70％和60％。

更新日期：2020-11-20

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