Design, Synthesis of 3-(5-Substituted Phenyl-[1,3,4]oxadiazol-2-yl)-1H-indole and Its Microbial Activity

被引：2

作者：

Suryawanshi, Manohar D. ^{[1
]}

Suryawanshi, Ganesh D. ^{[2
]}

Mhaske, Pravin C. ^{[3
]}

Karpe, Dnyaneshwar G. ^{[1
]}

Kamble, Komal R. ^{[1
]}

Rode, Sagar J. ^{[2
]}

Sudrik, Vilas A. ^{[1
]}

Lawande, Shamrao P. ^{[1
]}

机构：

[1] Shri Chhatrapati Shivaji Mahavidyalaya, Dept Chem, Ahmednagar 413701, Shrigonda, India

[2] Dept Chem, Dada Patil Mahavidyalaya, Karjat 414402, Ahmednagar, India

[3] Sir Parshurambhau Coll, Dept Chem, Pune 411030, India

来源：

CHEMISTRY & BIODIVERSITY | 2023年 / 20卷 / 03期

关键词：

indole; oxadiazole; microbial activity; Fischer indole synthesis; Vilsmeier-Haack formylation; INDOLE; INHIBITORS; NUCLEUS;

D O I：

10.1002/cbdv.202201017

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Fischer indole synthesis of indole by using phenyl-hydrazine and acetaldehyde resulted 1H-Indole while phenyl-hydrazine reacted with malonaldehyde gives 1H-Indole-3-carbaldehyde. Also Vilsmeier-Haack formylation of 1H-Indole gives 1H-Indole-3-carbaldehyde. 1H-Indole-3-carbaldehyde were oxidized to form 1H-Indole-3-carboxylic acid. 1H-Indole reacted with excess of BuLi at -78 degrees C using dry ice also gives 1H-Indole-3-carboxylic acid. Obtained 1H-Indole-3-carboxylic acid was converted to ester and ester in to acid hydrazide. Finally 1H-Indole-3-carboxylic acid hydrazide reacted with substituted carboxylic acid gives microbial active indole substituted oxadiazoles. Synthesized compounds 9a-j showing promising in vitro anti microbial activities against S. aureus bacteria compared with Streptomycin. Compound 9a, 9f and 9g showing activities against E. coli compared with standards. Compound 9a and 9f are found potent active against B. subtilis compared with reference standard while compound 9a, 9c and 9j active against S. typhi.

引用

页数：8

共 41 条

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Zhang, Wei-Hua ;

Yang, Guang-Fu ;

Gough, John .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 126 :669-674

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