Synthesis and Biological Evaluation of Novel 4-Morpholino-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine Derivatives Bearing Phenylpyridine/Phenylpyrimidine-Carboxamides

被引：4
|
作者：
Liu, Huimin [1 ]
Wang, Wenhui [2 ]
Sun, Chengyu [2 ,3 ]
Wang, Caolin [2 ]
Zhu, Wufu [2 ]
Zheng, Pengwu [2 ]
机构：
[1] Shanghai Inst Technol, Sch Perfume & Aroma Technol, Shanghai 201418, Peoples R China
[2] Jiangxi Sci & Technol Normal Univ, Sch Pharm, Nanchang 330013, Peoples R China
[3] Chongqing Three Gorges Med Coll, Affiliated Hosp, Dept Pharm, Chongqing 404000, Peoples R China
来源：
MOLECULES | 2016年 / 21卷 / 11期
关键词：
thiopyrano[4,3-d]pyrimidine; phenylpyridine/phenylpyrimidine carboxamides; synthesis; cytotoxicity activity; PI3K alpha kinase; C-MET INHIBITORS; PYRIMIDINE-DERIVATIVES; ANTICANCER ACTIVITY; DOCKING; MOIETY; DESIGN;
D O I：
10.3390/molecules21111447
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Four series of novel 4-morpholino-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine derivatives 11a-j, 12a-j, 13a-g and 14a-g bearing phenylpyridine/phenylpyrimidine-carboxamide scaffolds were designed, synthesized and their IC50 values against three cancer cell lines (A549, PC-3 and MCF-7) were evaluated. Eleven of the compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure-activity relationships (SARs) and pharmacological results indicated that the introduction of phenylpyridine-carboxamide scaffold was beneficial for the activity. What's more, the oxidation of the sulfur atom in thiopyran and various types of substituents on the aryl group have different impacts on different series of compounds. Furthermore, the positions of aryl group substituents have a slight impact on the activity of the phenylpyridine-carboxamide series compounds.
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页数：12
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