Design, synthesis, molecular prediction and biological evaluation of pyrazole-azomethine conjugates as antimicrobial agents

Abstract

A series of Schiff bases linked with heterocyclic moiety (6a–c, 7a–c, 11a–c, 12a–c, and 13a–c) and ferrocenyl Schiff bases (15a–c) were designed, synthesized, and confirmed based on the spectral data. Also, evaluations of their in vitro antibacterial and antifungal activities were performed and some Schiff bases (7a, 13a, b, and 15b) show moderate activities. Moreover, the physicochemical, pharmacokinetic, lipophilicity properties, druglikeness, ADME prediction, and toxicity properties of the newly Schiff bases (6a–c, 7a–c, 11a–c, 12a–c, and 13a–c) were predicted in silico. The results exhibited that some Schiff bases agree with druglikeness rules, inhibition of some CYP isoenzymes, and predicted as negative values on the carcinogenicity test. Also, all the Schiff bases exhibited more than 70% on the human intestinal absorption test, moderate permeation on the in vitro Caco-2 cell permeability test, and low permeability on the in vitro MDCK cell permeability test.

Graphical Abstract

Keywords:

• Antimicrobial activities
• azomethine-pyrazole
• ferrocene-2-carboxaldehyde
• heterocyclic moiety
• molecular prediction

Disclosure statement

No potential conflict of interest was reported by the author(s).

Acknowledgments

Authors thank National Research Centre for the financial support through scientific project number 12010103.