Synthesis, SAR and molecular docking studies of benzo[d]thiazole-hydrazones as potential antibacterial and antifungal agents. Issue 14 (15th July 2017)

• Record Type: Journal Article
• Authors: Zha, Gao-Feng; Leng, Jing; Darshini, N.; Shubhavathi, T.; Vivek, H.K.; Asiri, Abdullah M.; Marwani, Hadi M.; Rakesh, K.P.; Mallesha, N.; Qin, Hua-Li
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 14(2017)
• Page Start: 3148
• Page End: 3155
• Publication Date: 2017-07-15
• Subjects: Benzo[d]thiaozole -- SAR -- Antimicrobial -- Docking study; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.05.032
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A series of new benzo[ d ]thiazole-hydrazones analogues were synthesized and screened for their in vitro antibacterial and antifungal activities. The results revealed that compounds13, 14, 15, 19, 20, 28 and30 exhibited superior antibacterial potency compared to the reference drug chloramphenicol and rifampicin. Compounds5, 9, 10, 11, 12, 28 and30 were found to be good antifungal activity compared to the standard drug ketoconazole. A preliminary study of the structure-activity relationship (SAR) revealed that the antimicrobial activity depended on the effect of different substituents on the phenyl ring. The electron donating (OH and OCH3 ) groups presented in the analogues, increase the antibacterial activity (except compound12 ), interestingly, while the electron withdrawing (Cl, NO2, F and Br) groups increase the antifungal activity (except compound19 and20 ). In addition, analogues containing thiophene (28 ) and indole (30 ) showed good antimicrobial activities. Whereas, aliphatic analogues (24 –26 ) shown no activities in both bacterial and fungal stains even in high concentrations (100 µg/mL). Molecular docking studies were performed for all the synthesized compounds of which compounds11, 19 and20 showed the highest glide G-score.