Synthesis, Docking Study and Antifungal Activity Evaluation of Some 1,3-benzo[d]thiazole Analogs: A Promotion in Synthetic Method with Nano-γ-Al2O3/BF3-n under Solvent Free Conditions
Bi Bi Fatemah Mirjalili
Department of Chemistry, College of Science, Yazd University, Yazd, P.O.Box 89195-741, I. R., Iran.
Soghra Kabnadideh
Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Post code 7146864685, Shiraz, Iran, Shiraz, I.R., Iran.
Kamiar Zomorodian
Center of Basic Researches in Infectious Diseases and Department of Medical Mycology and Parasitology, School of Medicine, Shiraz University of Medical Sciences, Post code 71348-45794, Shiraz, Iran.
Leila Zamani *
Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Post code 7146864685, Shiraz, Iran, Shiraz, I.R., Iran.
Masoomeh Faghih
Department of Chemistry, College of Science, Yazd University, Yazd, P.O.Box 89195-741, I. R., Iran.
Zahra Haghighijoo
Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Science, Shiraz, Iran.
Samira Kananizadehgan
Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Science, Shiraz, Iran.
*Author to whom correspondence should be addressed.
Abstract
Aim: Nano-γ-Al2O3/BF3-n was applied for the synthesis of 1,3-benzo[d]thiazole derivatives as a new solid acid catalyst. Benzothiazole is used as a pharmacological agent with a wide variety of biological activities such as anticancer, antimicrobial, antitumor and antiviral properties. In the view we have synthesized a series of 1,3-benzo[d]thiazole derivatives (T1-T10) and screened for their antibacterial and antifungal abilities.
Methods: In this work, nano-γ-Al2O3/BF3-n was applied for the synthesis of 1,3-benzo[d]thiazole derivatives. Ten compounds (T1-T10) were screened for antimicrobial activity by broth micro dilution methods as recommended by CLSI.
Results: We have demonstrated a simple method for the synthesis of 1,3-benzo[d]thiazoles with using nano-γ-Al2O3/BF3-n as a new solid acid catalyst under solvent free condition at 110 °C .Also, of the tested compounds N1,N1-dimethyl-4-(1,3-benzothiazol-2-yl)aniline (T8) and 2(2-(4-nitrophenyl)-1,3-benzothiazole (T10) inhibited the growth of all examined fungi. Determination the probable binding model of compounds T8 and T10 in to Mycobacterium tuberculosis enzyme CYP51 active site was performed with docking simulation.
Conclusion: We have demonstrated a simple method for the synthesis of 1,3-benzo[d]thiazoles with using nano-γ-Al2O3/BF3-n as a new heterogeneous solid acid. Biological studies showed that some of the synthetic compounds including T8 and T10 exhibited a great activity against tested candida and dermatophytes.
Keywords: 1,3-Benzo[d]thiazole, 2-Aminothiophenol, Nano-γ-Al2O3/BF3-n, solvent free, antifungal, docking study