Synthesis of A New Series of N-Substituted-3-Indolyl-Heterocycles for Antimicrobial Evaluation - Egyptian Knowledge Bank

1385

Synthesis of A New Series of N-Substituted-3-Indolyl-Heterocycles for Antimicrobial Evaluation

Article

Last updated: 01 Jan 2025

Subjects

Abstract

CLAISEN-SCHMIDT reaction of N-ethyl (1a), N-benzyl (1b), N- .......benzoyl (1c), N-methylsulphonyl (1d) and N-benzenesulphonyl-3-acetylindoles (1e) with benzaldehyde gave 1-(N-substituted-1H-indol-3-yl)-3-phenyl-prop-2-ene-1-ones(2a-e). Cyclocondensation of 2a-e with urea, thiourea or guanidine led to the formation of pyrimidine derivatives 3a-e -5a-e, respectively. Base catalyzed reaction of 2a-e with ethyl acetoacetate gave cyclohexanone derivatives 6a-e, which were reacted with hydrazine hydrate to afford the indazole derivatives 7a-e. On the other hand, reaction of 2a-c with some hydrazine derivatives namely, hydrazine hydrate, acetyl hydrazine, phenyl hydrazine and benzyl hydrazine hydrochloride yielded the pyrazole derivatives 8a-c–11a-c, respectively. Moreover, reaction of 2a-c with hydroxyl amine hydrochloride gave the isoxazole derivatives 12a-c. The newly synthesized compounds were tested for their antimicrobial activity and the results revealed that, 4-(N-benzyl-1H-indol-3-yl)-6-phenyl-pyrimidin-2-amine (5b) showed potent growth inhibition activity at a concentration of 20 and 10 μg against Candida albicans (ATCC 10231) compared to reference drug cycloheximide.

DOI

10.21608/ejchem.2011.1385

Keywords

Claisen-Schmidt reaction, 3-Acetylindoles, Pyrimidine, pyrazole, Isoxazole and antimicrobial activity

Volume

Article Issue

Related Issue

303

Issue Date

2012-02-01

Receive Date

2011-05-02

Publish Date

2011-02-28

Page Start

141

Page End

154

Print ISSN

0449-2285

Online ISSN

2357-0245

Article File

EJCHEM_Volume 54_Issue 1_Pages 141-154.pdf

PDF . 536.6kB

Link

https://ejchem.journals.ekb.eg/article_1385.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=1385

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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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