The title compound 4-(5-(2,6-difluorophenyl)-1,3,4-oxadiazol-2-ylthio)-2-(trifluoromethyl)thieno[2,3-d]pyrimidine(C15H5F5N4OS2, Mr = 416.35) was designed and synthesized as antitumor agent, and its structure was deter...The title compound 4-(5-(2,6-difluorophenyl)-1,3,4-oxadiazol-2-ylthio)-2-(trifluoromethyl)thieno[2,3-d]pyrimidine(C15H5F5N4OS2, Mr = 416.35) was designed and synthesized as antitumor agent, and its structure was determined by 1H NMR, 13C NMR, MS, elemental analysis and single-crystal X-ray diffraction. The crystal belongs to monoclinic system, space group P21/c with a = 9.904(2), b = 10.057(2), c = 16.595(3) ?, β = 100.000(3)°, V = 1627.9(6) ?3, Z = 4, F(000) = 832, Dc = 1.699 g/cm3, μ = 0.395 mm-1, R = 0.0468 and wR = 0.1255 for 4726 independent reflections(Rint = 0.0336) and 2847 observed ones(I > 2σ(I)). The in vitro antitumor activity of the title compound was preliminarily evaluated by the standard MTT assay.展开更多
The physiologically active groups such as purine and pyrimidine bases are introduced to the asymmetric synthesis. The optically pure compounds bearing purine and pyrimidine bases (5a—5e) were prepared via the asymmet...The physiologically active groups such as purine and pyrimidine bases are introduced to the asymmetric synthesis. The optically pure compounds bearing purine and pyrimidine bases (5a—5e) were prepared via the asymmetric Michael addition reaction of purines and pyrimidines as Michael donators with the chiral source 5-(R)-[(lR, 2S, 5R)-menthyloxy]-2(5H)-furanone (3a), which was prepared from the natural chiral auxiliary (-)-menthol. The synthetic method was studied in detail and the new compounds were identified on the basis of their analytical data and spectroscopic data, such as [α] D 20 , IR, UV,1H NMR,13C NMR and MS. The absolute configuration of5a was established by X-ray crystallography. The results provided an efficient synthetic route to chiral purines and pyrimidine analogues, and offered chiral sources for further research on the physiologically active compounds of chiral nucleotides.展开更多
The crystal structure of the title compound has been determined by single crystal X ray diffraction analysis. C 15 H 14 N 4O 3, M r =298.30, monoclinic, space group P2 1/n, a=9.483(9), b=11.078(9), c...The crystal structure of the title compound has been determined by single crystal X ray diffraction analysis. C 15 H 14 N 4O 3, M r =298.30, monoclinic, space group P2 1/n, a=9.483(9), b=11.078(9), c=13.700(9), β=100.19(7)°, V=1417(4) 3, Z=4, D x =1.399 g.cm -3 , μ =0.0942 mm -1 ; F (000)=624, final R =0.074 and R w =0.074 for 1502 observed reflections〔 I≥3σ(I )〕. The results show that all ring atoms in the triazolopyrimidinyl moiety were coplanar with strong tensile force, which might be an important active site.展开更多
The crystal structure of the title compound has been determined bysingle crystal X-ray diffraction analysis. C14H9F3N6O4S, Mr = 414. 32, monoclinic,space group P21/n, a=8. 287(3), b= 24. 972(4), c= 8. 617(3)A, β= 108...The crystal structure of the title compound has been determined bysingle crystal X-ray diffraction analysis. C14H9F3N6O4S, Mr = 414. 32, monoclinic,space group P21/n, a=8. 287(3), b= 24. 972(4), c= 8. 617(3)A, β= 108. 36(3)°,V= 1693(2) A3, Z=4, Dx=1. 626 g. cm-3, μ=0. 2481 mm-1; F(000) =840, finalR = 0. 057 and Rw= 0. 057 for 1169 observed reflections [I≥3σ(I)]. The results showthat all ring atoms in the triazolopyrimidinyl moiety were coplanar with strong tensileforce, which might be an important active site.展开更多
基金supported by the National Natural Science Foundation of China(No.21262012)
文摘The title compound 4-(5-(2,6-difluorophenyl)-1,3,4-oxadiazol-2-ylthio)-2-(trifluoromethyl)thieno[2,3-d]pyrimidine(C15H5F5N4OS2, Mr = 416.35) was designed and synthesized as antitumor agent, and its structure was determined by 1H NMR, 13C NMR, MS, elemental analysis and single-crystal X-ray diffraction. The crystal belongs to monoclinic system, space group P21/c with a = 9.904(2), b = 10.057(2), c = 16.595(3) ?, β = 100.000(3)°, V = 1627.9(6) ?3, Z = 4, F(000) = 832, Dc = 1.699 g/cm3, μ = 0.395 mm-1, R = 0.0468 and wR = 0.1255 for 4726 independent reflections(Rint = 0.0336) and 2847 observed ones(I > 2σ(I)). The in vitro antitumor activity of the title compound was preliminarily evaluated by the standard MTT assay.
基金Project supported by the National Natural Science Foundation of China (Grant No. 29672004)
文摘The physiologically active groups such as purine and pyrimidine bases are introduced to the asymmetric synthesis. The optically pure compounds bearing purine and pyrimidine bases (5a—5e) were prepared via the asymmetric Michael addition reaction of purines and pyrimidines as Michael donators with the chiral source 5-(R)-[(lR, 2S, 5R)-menthyloxy]-2(5H)-furanone (3a), which was prepared from the natural chiral auxiliary (-)-menthol. The synthetic method was studied in detail and the new compounds were identified on the basis of their analytical data and spectroscopic data, such as [α] D 20 , IR, UV,1H NMR,13C NMR and MS. The absolute configuration of5a was established by X-ray crystallography. The results provided an efficient synthetic route to chiral purines and pyrimidine analogues, and offered chiral sources for further research on the physiologically active compounds of chiral nucleotides.
文摘The crystal structure of the title compound has been determined by single crystal X ray diffraction analysis. C 15 H 14 N 4O 3, M r =298.30, monoclinic, space group P2 1/n, a=9.483(9), b=11.078(9), c=13.700(9), β=100.19(7)°, V=1417(4) 3, Z=4, D x =1.399 g.cm -3 , μ =0.0942 mm -1 ; F (000)=624, final R =0.074 and R w =0.074 for 1502 observed reflections〔 I≥3σ(I )〕. The results show that all ring atoms in the triazolopyrimidinyl moiety were coplanar with strong tensile force, which might be an important active site.
文摘The crystal structure of the title compound has been determined bysingle crystal X-ray diffraction analysis. C14H9F3N6O4S, Mr = 414. 32, monoclinic,space group P21/n, a=8. 287(3), b= 24. 972(4), c= 8. 617(3)A, β= 108. 36(3)°,V= 1693(2) A3, Z=4, Dx=1. 626 g. cm-3, μ=0. 2481 mm-1; F(000) =840, finalR = 0. 057 and Rw= 0. 057 for 1169 observed reflections [I≥3σ(I)]. The results showthat all ring atoms in the triazolopyrimidinyl moiety were coplanar with strong tensileforce, which might be an important active site.
