Synthesis and SAR studies of pyrazole-3-carboxamides and-3-carbonyl thioureides including chiral moiety: Novel candidates as antibacterial agents

Bildirici İ., Cetin A., Mengeş N., Alan Y.

JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, vol.83, no.7-8, pp.795-807, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 83 Issue: 7-8
  • Publication Date: 2018
  • Doi Number: 10.2298/jsc170313029b
  • Journal Name: JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.795-807
  • Keywords: biological activity, chiral amino alcohols, pyrazole, heterocyclic compounds, BIOLOGICAL EVALUATION, PYRAZOLE DERIVATIVES, RECEPTOR LIGANDS, ANTITUMOR, IDENTIFICATION, DESIGN, POTENT, MICE
  • Van Yüzüncü Yıl University Affiliated: Yes

Abstract

A series of tetrasubstituted pyrazole-3-carboxamides (3a-c) and pyrazole-3-carbonyl thioureides (6a-c) were synthesized and their structures characterized by IR, NMR and elemental analysis. The antibacterial potential against specific Gram-positive and Gram-negative strains and the antifungal activities of all novel compounds were investigated. Structure-activity relationships (SAR) studies and some theoretical parameters (ClogP, CMR, PSA and ESP) of the compounds were performed on these two pyrazole derivatives. Pyrazole-3-carboxylate ester 2 was used for the synthesis of the carboxamide derivatives. The reactions of pyrazole-3-carbonyl isothiocyanate 5 with appropriate chiral amino alcohols were utilized for synthesizing the thioureide derivatives. Both of these types of pyrazole derivatives including a chiral moiety exhibited pronounced antibacterial activities. According to the present in vitro study, some of the promising compounds might be new candidates for a new generation of antibacterial drugs.