Synthesis of 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid derivatives and their antimicrobial activities

Şahan E., YILDIRIM I., Albayrak S.

HETEROCYCLIC COMMUNICATIONS, cilt.19, sa.3, ss.183-187, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 19 Sayı: 3
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1515/hc-2012-0167
  • Dergi Adı: HETEROCYCLIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.183-187
  • Erciyes Üniversitesi Adresli: Evet

Özet

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.