Safety of 4-(4-Bromophenyl)-5-methylthiazol-2-amine. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-(4-Bromophenyl)-5-methylthiazol-2-amine, is researched, Molecular C10H9BrN2S, CAS is 65705-44-4, about Unique Sulfur-Aromatic Interactions Contribute to the Binding of Potent Imidazothiazole Indoleamine 2,3-Dioxygenase Inhibitors. Author is Peng, Yi-Hui; Liao, Fang-Yu; Tseng, Chen-Tso; Kuppusamy, Ramajayam; Li, An-Siou; Chen, Chi-Han; Fan, Yu-Shiou; Wang, Sing-Yi; Wu, Mine-Hsine; Hsueh, Ching-Cheng; Chang, Jia-Yu; Lee, Lung-Chun; Shih, Chuan; Shia, Kak-Shan; Yeh, Teng-Kuang; Hung, Ming-Shiu; Kuo, Ching-Chuan; Song, Jen-Shin; Wu, Su-Ying; Ueng, Shau-Hua.
Indoleamine 2,3-dioxygenase (IDO1) inhibitors are speculated to be useful in cancer immunotherapy, but a phase III clin. trial of the most advanced IDO1 inhibitor, epacadostat, did not meet its primary endpoint and was abandoned. In previous work we identified the novel IDO1 inhibitor N-(4-chlorophenyl)-2-((5-phenylthiazolo[2,3-c][1,2,4]triazol-3-yl)thio)acetamide 1 through high-throughput screening (HTS). Herein, we report a structure-activity relationship (SAR) study of this compound, which resulted in the potent IDO1 inhibitor 1-(4-cyanophenyl)-3-(3-(cyclopropylethynyl)imidazo[2,1-b]thiazol-5-yl)thiourea 47 (hIDO IC50 = 16.4 nM). X-ray co-crystal structural anal. revealed that the basis for this high potency is a unique sulfur-aromatic interaction network formed by the thiourea moiety of 47 with the F163 and F226. This finding is expected to inspire new approaches towards the discovery of potent IDO1 inhibitors in the future.
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Reference:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics