Gao, Hui, Fu
2015
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Abstract
Two enantiomeric 2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine derivatives were synthesized by nucleophilic substitution of two chiral amines with 4-chloro-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine,which started from 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile,trifluoroacetic acid(TFA) and phosphoryl trichloride via one-pot procedure.Their structures were determined by single-crystal X-ray diffraction.Enantiomer(R)-3,(R)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system,space group P43 with a = 8.6847(6),b = 8.6847(6),c = 22.419(2) A,V= 1690.9(3) A3,Z = 4,Dc =1.428 g/cm3,μ = 0.228 mm-1,F(000) = 752,the final R = 0.0463 and wR = 0.1257 for 3442 observed reflections with I > 2σ(I).Enantiomer(S)-3,(S)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system,space group P41 with a = 8.688,b = 8.688,c = 22.421 A,V = 1692.4 A3,Z = 4,Dc = 1.426 g/cm3,μ = 0.227mm-1,F(000) = 752,the final R = 0.0682 and wR = 0.1806 for 3182 observed reflections with I >2σ(I).The preliminary bioassay indicated that the R-enantiomer exhibits higher antitumor activity against MCF-7 than gefitinib.