In 2015,Wang, Fang; Yang, Zhuang; Liu, Yibin; Ma, Liang; Wu, Yuzhe; He, Lin; Shao, Mingfeng; Yu, Kun; Wu, Wenshuang; Pu, Yuzhi; Nie, Chunlai; Chen, Lijuan published 《Synthesis and biological evaluation of diarylthiazole derivatives as antimitotic and antivascular agents with potent antitumor activity》.Bioorganic & Medicinal Chemistry published the findings.Name: Ethyl 2-amino-2-thioxoacetate The information in the text is summarized as follows:
By switching position of the N and S atom in the thiazole ring which were similar to the previously reported agent 5-(4-ethoxyphenyl)-4-(3′,4′,5′-trimethoxyphenyl)thiazol-2-amine, a series of 4,5-diarylthiazole derivatives were synthesized using Friedel-Crafts reaction based on chem. modification of Combrestatatin A-4 (CA-4). Their antiproliferative activities were evaluated and identified as new microtubule destabilizing agents. Structure-activity relation study indicated that compound 4-(4-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)thiazol-2-amine with 3,4,5-trimethoxyphenyl group at the C-4 position and 4-ethoxyphenyl group at the C-5 position of 2-amino substituted thiazole was of the most potent inhibitory activity in this series. 4-(4-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)thiazol-2-amine exhibits the IC50 values of 8.4-26.4 nM in five human cancer cell lines, with comparable inhibition effects to CA-4. Moreover, 4-(4-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)thiazol-2-amine showed potency as a tubulin polymerization inhibitor, with colchicine site binding ability and comparable extent of inhibition against the growth of P-glycoprotein over-expressing multidrug resistant cell lines. Mechanism studies revealed that 4-(4-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)thiazol2-amine could block the progression of cell cycle in the G2/M phase and result in cellular apoptosis in cancer cells. As a new tubulin destabilizing agent, 4-(4-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)thiazol-2-amine was also found high antivascular activity as it concentration-dependently reduced the cell migration and disrupted capillary like tube formation of HUVEC cells. Furthermore, 4-(4-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)thiazol2-amine significantly suppressed the tumor growth in HCT116 and SK-OV-3 xenograft models with tumor growth inhibitory rate of 55.12% and 72.7%, resp. The authors’ studies highlighted that 4-(4-Ethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)thiazol-2-amine was a promising microtubule targeting antitumor agent. In the part of experimental materials, we found many familiar compounds, such as Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1Name: Ethyl 2-amino-2-thioxoacetate)
Ethyl 2-amino-2-thioxoacetate(cas: 16982-21-1) belongs to anime. In organic chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines).Name: Ethyl 2-amino-2-thioxoacetate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics