取代 N-溴代酰胺基-2-氨基苯并噻唑的合成、SAR、分子对接和抗菌研究。
Synthesis, SAR, Molecular Docking and Anti-Microbial Study of Substituted N-bromoamido-2-aminobenzothiazoles.
机构信息
Department of Chemistry, Government of Maharashtra’s Ismail Yusuf College of Arts, Science and Commerce, Mumbai 60, India
Department of Chemistry, Chikitsak Samuha’s Patkar-Varde College of Arts, Science and Commerce, Goregaon (West), Mumbai 400 062, India
出版信息
Curr Comput Aided Drug Des. 2020;16(5):530-540. doi: 10.2174/1573409915666190902143648.
BACKGROUND
Benzothiazoles are reported to have bioorganic and pharmaceutical chemistry applications.
INTRODUCTION
A series of substituted N-bromoamido-2-aminobenzothiazoles was synthesized from substituted anilines via 2-aminobenzothiazoles and it was further evaluated for its antimicrobial activity.
METHODS
All the newly synthesized compounds were characterized by FT-IR, NMR and mass spectra and purity profiles were studied by HPLC analysis. The antimicrobial testing (MIC determination) was newly performed with agar micro-broth dilution method for these analogs.
RESULTS
Among the synthesized compound 3b showed the highest activity with MIC value of 3.12 μg/mL against Bacillus, E. coli, S. aureus and Klebsiella and 6.25 μg/mL against C. albicans. The ADME properties as calculated by using Qikprop were found within acceptable range. Derivatives shows a good-moderate binding affinity towards target Cytochrome P450 14 alpha-sterol demethylase (CYP51) (PDB ID: 1EA1).
CONCLUSION
Our in-silico and in-vitro studies on a series of substituted aminobenzothiazoles may be helpful for further designing of more potent antimicrobials in future.
背景
苯并噻唑据报道具有生物有机和药物化学应用。
简介
通过 2-氨基苯并噻唑，从取代苯胺合成了一系列取代的 N-溴酰胺-2-氨基苯并噻唑，并进一步评估了其抗菌活性。
方法
所有新合成的化合物均通过傅里叶变换红外光谱（FT-IR）、核磁共振（NMR）和质谱进行了表征，并通过高效液相色谱（HPLC）分析研究了其纯度曲线。采用琼脂微量肉汤稀释法对这些类似物进行了新的抗菌测试（MIC 测定）。
结果
在所合成的化合物中，3b 显示出最高的活性，对芽孢杆菌、大肠杆菌、金黄色葡萄球菌和克雷伯氏菌的 MIC 值为 3.12 μg/mL，对白色念珠菌的 MIC 值为 6.25 μg/mL。使用 Qikprop 计算的 ADME 性质在可接受范围内。衍生物对靶细胞色素 P450 14 alpha-甾醇去甲基酶（CYP51）（PDB ID：1EA1）表现出良好的中等结合亲和力。
结论
我们对一系列取代的氨基苯并噻唑的计算机和体外研究可能有助于未来进一步设计更有效的抗菌药物。
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