Tricyclic thiazoles are a new class of angiogenesis inhibitors

Abstract

Tricyclic thiazoleamine derivatives that were identified as hits in a screen against human umbilica vein endothelial cell proliferation were subjected to a structure-activity relationship study. Two structurally superimposable scaffolds—4H-thiochromeno[4,3- d]thiazol-2-amine and 5,6-dihydro-4H-benzo[6,7]cyclohepta[1,2-d]thiazol-2-amine derivatives—yielded low-micromolar inhibitors, and two among them 37 and 43 also exhibited antiangiogenic activity in an endothelial tube formation assay Thus, 37 and 43 can serve as leads to develop a novel class of antiangiogenic agents.

Copper-mediated [3 + 2] oxidative cyclization of oxime acetate and its utility in the formal synthesis of fentiazac

“…7, 145.6, 132.8, 132.7, 132.4, 131.7, 130.1, 127.8, 107.4 6, 146.0, 129.1, 128.4, 126.7, 123.8, 123.5, 122.3, 121.4, 121.3, 121.1, 120.5, 101.3 4,thiazol-2-amine (2m). 25 Brown semi-solid; 25 mg; yield 57%; R f : 0.1 (8 : 2, EA : Pet ether); IR (ν cm −1 ): 3439 (w), 3263 (w), 1599 (w), 1529 (s), 1339 (s), 1062 (s), 763 (s), 739 (s), 1 H NMR (500 MHz, DMSO-d 6 ): δ 7.52 (d, J = 7.5 Hz, 1H), 7. 22-7.16 (m, 2H), 7.11 (td, J 1 = 7.5 Hz, J 1 = 1.2 Hz, 1H), 6.95 (s, 2H), 2.93 (t, J = 7.9 Hz, 2H), 2.76 (t, J = 7.9 Hz, 2H); 13 C NMR (126 MHz, ): δ 167.…”

Synthetic routes to benzosuberone-based fused- and spiro-heterocyclic ring systems

“…41 3.1.6 Benzosuberone fused with thiazoles. Condensation of 1-benzosuberone 2a with thiourea in the presence of iodine at 100 C yielded the seven-membered tricyclic thiazoleamine 80, which upon treatment with 2,6-diuorobenzoyl chloride 81 in dichloromethane (DCM) in the presence of triethylamine, afforded the corresponding benzamide derivative 82 49 The structures of compounds 96 were established based on their spectral data and elemental analyses. 40 3.1.10 Benzosuberone fused with selenadiazoles.…”

Insight on [1,3]thiazolo[4,5-e]isoindoles as tubulin polymerization inhibitors

“…Several examples of benzo-fused derivatives, including benzothiazoles (BTA), have been used in clinical practice to treat various diseases with high therapeutic potency, including cancer [16][17][18][19]. Tricyclic structures incorporating the thiazole nucleus of types 5-7 (Chart 2) were considered for the design of new drug-like molecules [20][21][22]. For several years, we designed a number of classes of small molecules endowed with biological activity [23][24][25][26][27][28][29][30][31][32][33][34][35].…”