Synthesis of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid derivatives and their antimicrobial activities
HETEROCYCLIC COMMUNICATIONS, vol.19, no.3, pp.183-187, 2013 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 19 Issue: 3
- Publication Date: 2013
- Doi Number: 10.1515/hc-2012-0167
- Journal Name: HETEROCYCLIC COMMUNICATIONS
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.183-187
- Erciyes University Affiliated: Yes
Abstract
The reaction of 1H-pyrazole-3-carboxylic acid chloride (1) with various hydrazine derivatives 2a-c yielded the corresponding N,N-disubstituted 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carbohydrazides 3a-c. These products underwent Friedel-Crafts acylations with arenes to afford compounds 4a-c. Treatment of 1 with aromatic diamines produced 1H-pyrazole-3-carboxamides 5a-c, which were allowed to react with phenylhydrazine to give hydrazone derivatives 6a-c. The structures of all new compounds were established by IR, H-1 and C-13 NMR data and elemental analyses. The new compounds were evaluated for antimicrobial activities against Gram (-), Gram (+) bacteria and two yeasts using the disc diffusion method. N,N-Dimethylhydrazide derivative 3a is the most active compound of the series.