Some New 2-Amino-4-(N-substituted-1H- indol - 3-yl) thiophene-3-carbonitriles and their Antimicrobial Properties - Egyptian Knowledge Bank

1153

Some New 2-Amino-4-(N-substituted-1H- indol - 3-yl) thiophene-3-carbonitriles and their Antimicrobial Properties

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Last updated: 01 Jan 2025

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Abstract

ANOVEL series of 2-amino-4-(N-substituted-1H-indol-3-yl) thiophene-3-carbonitriles (3a-f) were prepared via reaction of 2-(1-(N-substituted -1H-indol-3-yl) ethylidene) malononitriles (2a-f) with sulfur (Gewald reaction). Reaction of 3a-f with formic acid, formamide or malononitrile led to the formation of fused thieno [2,3-d] pyrimidin-4(3H)-ones (6a-f) thieno[2,3-d] pyrimidin-4-amines (7a-f) and thieno[2,3-d] pyridine-3-carbonitriles (8a-f), respectively. On the other hand, a series of 2-(2-(4-nitrophenyl)-4-oxothiazolidin-3-yl)-4-(N-substituted-1H-indol-3-yl) thiophene-3-carbonitriles (10a-f) and N-3- [3-cyano-4-(N-substituted-1H-indol-3-yl)- (2-thienyl) -4-oxo-2- imino thiazolidinylidenes (12a-f), were prepared via reaction of Schiff bases 9a-f with thioglycollic acid or reaction of chloroacetamids 11a-f with potassium thiocyanate, respectively. Moreover, reaction of 3a-f with ethylenediamine yielded 3-(4,5-dihydro-1H-imidazol-2-yl)-4-(N-substituted-1H-indol-3yl) thiophen-2-amines (13a-f). The antimicrobial activity of the newly synthesized compounds revealed that, 2-(2-(naphthalene-1-yl)diazenyl)-4-(N-substituted-1H-indol-3-yl)thiophene-3-carbonitriles (4a-f) showed potent inhibition of 25-33 and 18-26mm at a dose of 20 and 10 μg per disc, respectively towards Aspergillus fumigatus compared to reference drug cycloheximide.

DOI

10.21608/ejchem.2012.1153

Keywords

ndole, 2-Aminothiophene-3-carbonitriles, 3-d] pyrimidine, Thieno [2, 3-d] pyridine, Thiazolidine and Antimicrobial activity

Volume

Article Issue

Related Issue

281

Issue Date

2012-06-01

Receive Date

2012-07-03

Publish Date

2012-06-30

Page Start

239

Page End

258

Print ISSN

0449-2285

Online ISSN

2357-0245

Article File

EJCHEM_Volume 55_Issue 3_Pages 239-258.pdf

PDF . 601.9kB

Link

https://ejchem.journals.ekb.eg/article_1153.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=1153

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Type Code

292

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

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