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Citation: NIE Yao, HUANG Dong-Hai, WANG Fa-Song, DAN You-Meng, ZHAO Jin-Shun, SONG Xin-Jian. Syntheses, Crystal Structures, and Antitumor Activities of Two 2-Trifluoromethyl-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-4-amine Derivatives[J]. Chinese Journal of Structural Chemistry, ;2014, 33(12): 1789-1795. doi: 10.14102/j.cnki.0254-5861.2011-0478 shu

Syntheses, Crystal Structures, and Antitumor Activities of Two 2-Trifluoromethyl-5,6,7,8-tetrahydrobenzo[4,5]-thieno[2,3-d]pyrimidin-4-amine Derivatives

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a. Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province, Hubei University for Nationalities, Enshi 445000, China;
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b. School of Chemical and Environmental Engineering, Hubei University for Nationalities, Enshi 445000, China

Received Date: 15 August 2014
Available Online: 14 October 2014
Fund Project: Supported by the National Natural Science Foundation of China (No. 21262012) (No. 21262012) the State Undergraduate Innovative Training Program of Hubei University for Nationalities (No. 201310517001) (No. MY2014T004) the Project of New Strategic Industries for Fostering Talents in Applied Chemistry of Higher Education of Hubei Province, and the Open Fund of Key Laboratory of Biologic Resources Protection & Utilization of Hubei Province (No. PKLHB1306) (No. 201310517001)

Two novel 2-trifluoromethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-amine derivatives were synthesized by nucleophilic substitution of two appropriate amines with 4-chloro-2-(trifluoromethyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidine, which started from 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile, trifluoroacetic acid (TFA) and phosphorous oxychloride by one-pot procedure. Their structures were determined by single-crystal X-ray diffraction. Compound 1, N-(furan-2-ylmethyl)-2-trifluoromethyl-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4-amine, crystallizes in the monoclinic system, space group C2/c with a=26.352(3), b=7.5991(8), c=17.1423(18)Å, β=114.667(2)°, V=3119.5(6)Å³ and Z=8. Compound 2, N-(3-silatranylpropyl)-2-trifluoromethyl-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4-amine, crystallizes in the monoclinic system, space group P2₁/n with a=13.4394(13), b=8.9446(9), c=18.9657(18)Å, β=101.9640(10)°, V=2230.3(4)Å³ and Z=4. The preliminary bioassay indicated that compound 2 exhibits more potent antitumor activity against BCG-823 than 5-fluorouracil (5-FU).
- thieno[2,3-d]pyrimidine,
- facile synthesis,
- trifluoromethyl,
- antitumor activity
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