Citation: Liu Jingbo, Li Fengyun, Wang Yuanhong, Zhang Haoxuan, Dong Jingyue, Sun Pengwei, Li Yuxin, Li Zhengming. Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4, 5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety[J]. Chinese Chemical Letters, ;2019, 30(3): 668-671. doi: 10.1016/j.cclet.2018.11.001 shu

Synthesis, biological activities and 3D-QSAR studies of (R)-2-phenyl-4, 5-dihydrothiazole-4-carboxamide derivatives containing a sulfur ether moiety

a.
College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, China
b.
College of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China
c.
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China

liyx128@nankai.edu.cn

nkzml@vip.163.com

Received Date: 23 September 2018
Revised Date: 28 October 2018
Accepted Date: 2 November 2018
Available Online: 1 March 2018

Figures(2)

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.
- (R)-2-Phenyl-4, 5-dihydrothiazole-4-carboxamide,
- Sulfur ether,
- Antifungal activity,
- SARs,
- CoMSIA model
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沈阳化工大学材料科学与工程学院沈阳 110142