1492891-14-1Relevant articles and documents
Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety
Liu, Jingbo,Li, Fengyun,Wang, Yuanhong,Zhang, Haoxuan,Dong, Jingyue,Sun, Pengwei,Li, Yuxin,Li, Zhengming
supporting information, p. 668 - 671 (2018/11/27)
A series of (R)-2-phenyl-4,5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety were synthesized and characterized on the basis of NMR and elemental analysis (EA). The crystal structure of (R)-N-(2-methyl-1-(methylthio)propan-2-yl)-2-(4-nitrophenyl)-4,5-dihydrothiazole-4-carboxamide (13d) was determined to show R configuration. The bioasssy results indicated that most title compounds displayed good and broad spectrum antifungal activities against several phytopathogenic fungi. The structure activity relationships were discussed. Based on the antifungal activity of title compounds against Phytophthora capsici, a CoMSIA calculation was performed to establish a 3D-QSAR model, which revealed that electrostatic and hydrophobic fields were the two most significant factors for antifungal activity. According to the established 3D-QSAR model, structure optimization was carried out to find (R)-N-((R)-1-(methylthio)propan-2-yl)-2-(p-tolyl)-4,5-dihydrothiazole-4-carboxamide (15h) with excellent activity against Phytophthora capsici, thus emerging as a new lead compound for novel antiphytopathogenic fungus agent development.
Cu(i)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates: Synthesis of 4,4′-bithiazoline derivatives
Fang, Xinxin,Zhang, Kaifan,Yao, Hequan,Huang, Yue
supporting information, p. 8030 - 8034 (2016/09/09)
Cu(i)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates with good functional group tolerance has been developed. The methodology presented an efficient method to directly construct vicinal carbon-hetero quaternary centers existing in numerous functional molecules and could be applied to the synthesis of 4,4′-bithiazoles which are difficult to prepare by direct C-H activation.
Semi-synthesis and anti-lung cancer activity evaluation of aryl dihydrothiazol acyl podophyllotoxin ester derivatives
Lin, Hong-Yan,Bai, Li-Fei,Wang, Fang,Wu, Xun,Han, Lu-Jing,Baloch, Shahla Karim,Yang, Yong-Hua,Wang, Xiao-Ming
, p. 27775 - 27784 (2015/03/31)
Lung cancer is the leading cause of cancer death worldwide, making it one of the biggest concerns for chemoprevention. In this study, we obtained seventeen potent anticancer agents through semi-synthesis based on a natural product, podophyllotoxin. Despite prior studies of podophyllotoxin derivatives being focussed on DNA-topoisomerase II, we now turn our attention to their effect on tubulin. The MTT assay screened out the most potent anticancer agent, S12 (IC50 = 0.18 μM against A549 cell line), and it showed lower cytotoxicity against normal cells. Next, the flow cytometry analysis result demonstrated that it can cause a remarkable cell cycle arrest at G2/M phase but the effect on apoptosis is not very significant. In addition, docking simulation results showed that S12 can nicely bound to the colchicine binding site of tubulin. Furthermore, we confirmed that S12 can really inhibit tubulin polymerization through confocal microscopy and protein expression determination assay.
