Synthesis, Characterization and Antimicrobial Evaluation with DFT Study of New Two-Amino-4-(4-Chlorophenyl) Thiazole Derivatives

  • Ammar A Mahmood Kubba
  • Nedaa A. A. Rahim

Abstract

2-amino-4-(4-chloro phenyl)-1,3-thiazole (1) was synthesized by refluxing thiourea with para-chloro phenacyl bromide in absolute methanol. The condensation of amine compound (1)  with phenylisothiocyanate in the presence of pyridine will  produce 1-(4-(4-chlorophenyl)thiazol-2-yl)-3-phenylthiourea(2), which is  upon treatment with 2,4 dinitrophenyl hydrazine by conventional method, afforded 1- ( 4 - ( 4 – chlorophenyl ) thiazol – 2 – yl ) – 3 - phenylhydrazonamide,N' - ( 2 , 4 -dinitrophenyl) ,(3).The characterization of the titled compounds were performed utilizing FTIR spectroscopy, 1HNMR and CHNS elemental analysis, and by measurements of  their  physical properties.  The synthesized compounds had been screened for their, in vitro  preliminary antimicrobial activity against three Gram-positive bacteria: (Staph. aureus, Micrococcus luteus and  Bacillus subtilis) and three Gram-negative bacteria : (Pseud.aeruginosa, E.coli and  Proteus mirabilis) ,and two fungal strains(Candida albicans and Candida glabrata ), using a minimum  inhibitory concentration (MIC) of 100 µg\ml of  test compound, by  well diffusion method.


 The derivatives showed moderate antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis & high antifungal activity against Candida glabrata and Candida albicans. Computational study was performed to calculate some of thermodynamic parameters by using density functional theory (DFT)

Published
Jun 20, 2018
How to Cite
A MAHMOOD KUBBA, Ammar; A. A. RAHIM, Nedaa. Synthesis, Characterization and Antimicrobial Evaluation with DFT Study of New Two-Amino-4-(4-Chlorophenyl) Thiazole Derivatives. Iraqi Journal of Pharmaceutical Sciences ( P-ISSN: 1683 - 3597 , E-ISSN : 2521 - 3512), [S.l.], v. 27, n. 1, p. 79-88, june 2018. ISSN 1683-3597. Available at: <http://www.bijps.com/index.php/bijps/article/view/776>. Date accessed: 23 sep. 2018. doi: http://dx.doi.org/10.31351/vol27iss1pp79-88.