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Synthesis and Biological Evaluation of Pyrazoline Derivatives Bearing an Indole Moiety as New Antimicrobial Agents
Author(s) -
Özdemir Ahmet,
Altintop Mehlika Dilek,
Kaplancıklı Zafer Asim,
TuranZitouni Gülhan,
Karaca Hülya,
Tunalı Yağmur
Publication year - 2013
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201200479
Subject(s) - moiety , chemistry , antimicrobial , pyrazoline , candida glabrata , acetic acid , stereochemistry , hydrochloride , brine shrimp , minimum inhibitory concentration , indole test , klebsiella pneumoniae , chemical synthesis , aryl , combinatorial chemistry , organic chemistry , escherichia coli , candida albicans , microbiology and biotechnology , in vitro , biochemistry , traditional medicine , biology , medicine , gene , alkyl
1‐( p ‐Methylphenyl)‐3,5‐diaryl‐2‐pyrazoline derivatives ( 2a–f ) were synthesized via the treatment of 1‐(1 H ‐indol‐3‐yl)‐3‐aryl‐2‐propen‐1‐ones ( 1a–f ) with p ‐methylphenylhydrazine hydrochloride in hot acetic acid. The structures of these compounds were elucidated by IR, 1 H NMR, and mass spectral data and elemental analysis. These compounds were investigated for their antimicrobial activity. Brine‐Shrimp lethality assay was carried out to determine the toxicity of the compounds. Compound 2e , which is the pyrazoline derivative bearing the 2,5‐dichlorophenyl moiety, can be identified as the most promising agent against Klebsiella pneumoniae (ATCC 13883) and Candida glabrata (ATCC 36583) due to its inhibitory effects on K. pneumoniae and C. glabrata with a MIC value of 100 µg/mL as a non‐toxic agent (LC 50 > 1000 µg/mL).