Gao, Ya; Huang, Dai-Chuan; Liu, Chang; Song, Zi-Long; Liu, Jing-Rui; Guo, Shu-Ke; Tan, Jun-Yang; Qiu, Run-Ling; Jin, Bing; Zhang, Haifeng; Mulholland, Nick; Han, Xinya; Xia, Qinfei; Ali, Abdallah S.; Guo, Dale; Deng, Yun; Gu, Yu-Cheng; Zhang, Ming-Zhi published the artcile< Streptochlorin analogues as potential antifungal agents: Design, synthesis, antifungal activity and molecular docking study>, Computed Properties of 3959-07-7, the main research area is streptochlorin analog synthesis antifungal agent mol docking; Antifungal activity; Imidazole; Molecular docking; Natural products; Streptochlorin.
Streptochlorin is a small mol. of indole alkaloid isolated from marine Streptomyces sp., it is a promising lead compound due to its potent bioactivity in preventing many phytopathogens in our previous study, but further structural modifications are required to improve its antifungal activity. Our work in this paper focused on the replacement of oxazole ring in streptochlorin with the imidazole ring, to discover novel analogs. Based on this design strategy, three series of streptochlorin analogs were efficiently synthesized through sequential Vilsmeier-Haack reaction, Van Leusen imidazole synthesis and halogenation reaction. Some of the analogs displayed excellent activity in the primary assay, and this is highlighted by compounds I and II, the growth inhibition against Alternaria Leaf Spot and Rhizoctorzia solani under 50μg/mL are 97.5% and 90.3%, resp., even more active than those of streptochlorin, pimprinine and Osthole. Mol. docking models indicated that streptochlorin binds with Thermus thermophiles Leucyl-tRNA Synthetase in a similar mode to AN2690, offering a perspective on the mode of action study for antifungal activities of streptochlorin derivatives Further study is still ongoing with the aim of discovering synthetic analogs, with improved antifungal activity and clear mode of action.
Bioorganic & Medicinal Chemistry published new progress about Cyclization. 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Computed Properties of 3959-07-7.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary