The title compound 6-chloro-l-((6-chloropyridin-3-yl)methyl)-3-phenyl-lH-benzofuro[3,2-c]pyrazole(5,C21H13Cl2N3O,Mr = 394.26) was synthesized and characterized by elemental analysis,^1H NMR,^13C NMR and X-ray si...The title compound 6-chloro-l-((6-chloropyridin-3-yl)methyl)-3-phenyl-lH-benzofuro[3,2-c]pyrazole(5,C21H13Cl2N3O,Mr = 394.26) was synthesized and characterized by elemental analysis,^1H NMR,^13C NMR and X-ray single-crystal diffraction.The structure reveals that the crystal belongs to the triclinic system,space group P1 with a = 7.8829(8),b = 10.3281(10),c = 11.7615(12)A°,α = 83.5552(2),β = 79.921(2),γ = 70.189(2)°,V= 885.54(15) A°3,Z = 2,Dc =1.479 g/cm^3,μ = 0.383 mm^-1,F(000) = 404,R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I 〉 2σ(I).The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction.In addition,the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.展开更多
The title compound N-((2,6-difluorophenyl)carbamoyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide(C13H12F2N4O2) was synthesized, and its structure was confirmed by ^1H NMR,HRMS and X-ray diffraction. It crystallizes ...The title compound N-((2,6-difluorophenyl)carbamoyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide(C13H12F2N4O2) was synthesized, and its structure was confirmed by ^1H NMR,HRMS and X-ray diffraction. It crystallizes in the monoclinic system, space group P21/c with a = 9.50(2), b = 10.11(2), c = 14.07(3) A^°, β = 102.15(3)°, Dc = 1.480 g/cm^3, Z = 4, V = 1320(5) A^°3, the final R = 0.0789 and wR = 0.1860 for 1054 observed reflections with I 〉 2σ(I). The preliminary biological test shows that the title compound has weak antifungal activities.展开更多
Compounds 1 (C15H17C1F3N303, Mr = 379) and 2 (C14H14C1F3N4OS, Mr = 378) have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction. Crystal 1 belongs to the triclinic sy...Compounds 1 (C15H17C1F3N303, Mr = 379) and 2 (C14H14C1F3N4OS, Mr = 378) have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction. Crystal 1 belongs to the triclinic system, space group P1 with a = 6.0223(19), b = 9.324(3), c = 15.936(5) A, a = 80.687(5), β= 87.289(5), ), = 86.097(5)°, V= 880.4(5) A3, Z = 2, Dc = 1.433 g/cm3,μ(MoKa) = 0.266 mm^-1, F(000) = 392, R = 0.0861 and wR = 0.1999 for 2022 observed reflections with I 〉 2o(/). Crystal 2 belongs to the triclinic system, space group PI with a = 7.7029(15), b = 8.3371(16), c = 14.410(3) A, a = 100.672(3), β= 103.168(3), ? = 98.726(3)°, V = 876.1(3) A3, Z = 2, Dc= 1.451 g/cm^3,μ(MoKa) = 0.379 mm^-1, F(000) = 388, R = 0.0672 and wR = 0.2105 for 2725 observed reflections with I 〉 2σ(I). Although the two compounds are similar with the same pyrazole and pyrethroid units, X-ray analysis reveals that their structures are completely different.展开更多
Compounds 1 (C17H22N2,Mr =254.37) and 2 (C13H16N2,Mr=200.28) have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction.Crystal 1 belongs to triclinic,space group P(1)...Compounds 1 (C17H22N2,Mr =254.37) and 2 (C13H16N2,Mr=200.28) have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction.Crystal 1 belongs to triclinic,space group P(1) with a =6.524(2),b =8.987(3),c =12.746(5) A,α =95.220(7),β =90.055(6),γ =104.431(6)°,V =720.5(4) A^3,Z =2,Dc =1.173 g/cm^3,μ(MoKα) =0.069 mm1,F(000) =276,R =0.0578 and wR =0.1221 for 1487 observed reflections Ⅰ 〉 2o(Ⅰ).Crystal 2 is of tetragonal system,space group Ⅰ41/a with a =20.763(10),b =20.763(10),c =11.427(6) A,V=4926(4) A3,Z =16,Dc =1.080 g/cm^3,μ(MoKα) =0.065 mm-1,F(000) =1728,R =0.0581 and wR =0.1288 for 1408 observed reflections with Ⅰ 〉 2σ(Ⅰ).Although the two compounds are similar with the same pyrazole and benzene ring units,X-ray analysis reveals that their structures are completely different maybe caused by steric effects.展开更多
Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^(13) C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of th...Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^(13) C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani,Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC_(50) values of 0.013, 1.608 and 1.874 mg/m L, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC_(50) value of 22.21 mg/m L. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.展开更多
A series of novel pyrazole fused heterocyclic derivatives were synthesized via a two-step procedure or a one-pot two step method, and their catalytic DNA cleavage abilities and anti-BVDV activities were also evaluated...A series of novel pyrazole fused heterocyclic derivatives were synthesized via a two-step procedure or a one-pot two step method, and their catalytic DNA cleavage abilities and anti-BVDV activities were also evaluated. The results obtained indicated that compounds 3b-3c could catalyze the cleavage of supercoiled DNA (pUC 19 plasmid DNA) to nicked DNA under physiological conditions with high yields via a hydrolytic mechanism. The studies on anti-viral activities against bovine viral diarrhea virus (BVDV) demonstrated that some of the pyrazole derivatives showed pronounced anti-BVDV activity with interesting ECso values and no significant cytotoxicity. Among them, compound 31 showed the highest antiviral activity (ECso = 0.12 μmol/L) and was 10 fold more than that of the positive control ribavirin (ECso = 1.3 μmol/L), which provided a potential candidate for the development of anti-BVDV agents.展开更多
A series of novel N-(3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their...A series of novel N-(3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis (L) Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.展开更多
基金supported by the National Natural Science Foundation of China(No.21002048)the Project of Outstanding Young Teachers in Guangdong Province(No.C1032190)
文摘The title compound 6-chloro-l-((6-chloropyridin-3-yl)methyl)-3-phenyl-lH-benzofuro[3,2-c]pyrazole(5,C21H13Cl2N3O,Mr = 394.26) was synthesized and characterized by elemental analysis,^1H NMR,^13C NMR and X-ray single-crystal diffraction.The structure reveals that the crystal belongs to the triclinic system,space group P1 with a = 7.8829(8),b = 10.3281(10),c = 11.7615(12)A°,α = 83.5552(2),β = 79.921(2),γ = 70.189(2)°,V= 885.54(15) A°3,Z = 2,Dc =1.479 g/cm^3,μ = 0.383 mm^-1,F(000) = 404,R = 0.0538 and wR = 0.1335 for 2453 observed reflections with I 〉 2σ(I).The result reveals that the crystal structure of the title compound 5 is stabilized by three C-Cl…π interactions and π…π stacking interaction.In addition,the preliminary investigation showed that 5 exhibits remarkably good antitumor activity against the MCF-7 and A549 cell lines.
基金funded by Natural Science Foundation of Zhejiang Province(No.LY16C140007)National Natural Science Foundation of China(No.31401691)
文摘The title compound N-((2,6-difluorophenyl)carbamoyl)-1,3-dimethyl-1 H-pyrazole-4-carboxamide(C13H12F2N4O2) was synthesized, and its structure was confirmed by ^1H NMR,HRMS and X-ray diffraction. It crystallizes in the monoclinic system, space group P21/c with a = 9.50(2), b = 10.11(2), c = 14.07(3) A^°, β = 102.15(3)°, Dc = 1.480 g/cm^3, Z = 4, V = 1320(5) A^°3, the final R = 0.0789 and wR = 0.1860 for 1054 observed reflections with I 〉 2σ(I). The preliminary biological test shows that the title compound has weak antifungal activities.
基金supported by Hubei University of Technology,Science and Technology Department of Hubei Province(No.ZRY0981)National Natural Science Foundation of China(No.21272086)
文摘Compounds 1 (C15H17C1F3N303, Mr = 379) and 2 (C14H14C1F3N4OS, Mr = 378) have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction. Crystal 1 belongs to the triclinic system, space group P1 with a = 6.0223(19), b = 9.324(3), c = 15.936(5) A, a = 80.687(5), β= 87.289(5), ), = 86.097(5)°, V= 880.4(5) A3, Z = 2, Dc = 1.433 g/cm3,μ(MoKa) = 0.266 mm^-1, F(000) = 392, R = 0.0861 and wR = 0.1999 for 2022 observed reflections with I 〉 2o(/). Crystal 2 belongs to the triclinic system, space group PI with a = 7.7029(15), b = 8.3371(16), c = 14.410(3) A, a = 100.672(3), β= 103.168(3), ? = 98.726(3)°, V = 876.1(3) A3, Z = 2, Dc= 1.451 g/cm^3,μ(MoKa) = 0.379 mm^-1, F(000) = 388, R = 0.0672 and wR = 0.2105 for 2725 observed reflections with I 〉 2σ(I). Although the two compounds are similar with the same pyrazole and pyrethroid units, X-ray analysis reveals that their structures are completely different.
基金Supported by Hubei University of Technology,Science and Technology Department of Hubei Province(No.2012FFB00706)National Natural Science Foundation of China(No.21272086)
文摘Compounds 1 (C17H22N2,Mr =254.37) and 2 (C13H16N2,Mr=200.28) have been synthesized and their crystal structures were determined by single-crystal X-ray diffraction.Crystal 1 belongs to triclinic,space group P(1) with a =6.524(2),b =8.987(3),c =12.746(5) A,α =95.220(7),β =90.055(6),γ =104.431(6)°,V =720.5(4) A^3,Z =2,Dc =1.173 g/cm^3,μ(MoKα) =0.069 mm1,F(000) =276,R =0.0578 and wR =0.1221 for 1487 observed reflections Ⅰ 〉 2o(Ⅰ).Crystal 2 is of tetragonal system,space group Ⅰ41/a with a =20.763(10),b =20.763(10),c =11.427(6) A,V=4926(4) A3,Z =16,Dc =1.080 g/cm^3,μ(MoKα) =0.065 mm-1,F(000) =1728,R =0.0581 and wR =0.1288 for 1408 observed reflections with Ⅰ 〉 2σ(Ⅰ).Although the two compounds are similar with the same pyrazole and benzene ring units,X-ray analysis reveals that their structures are completely different maybe caused by steric effects.
基金supported by National Key Research and Development Program of China(No.2016YFC0502004-2)Applied Basic Research Program of Sichuan Province(No.2014JY0063)
文摘Twenty-seven novel pyrazole carboxamides with diarylamine-modified scaffold were designed,synthesized and characterized in detail via1 H NMR,^(13) C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani,Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC_(50) values of 0.013, 1.608 and 1.874 mg/m L, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC_(50) value of 22.21 mg/m L. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.
基金the National Natural Science Foundation of China (Nos.21105091 and 20772113) for the financial support
文摘A series of novel pyrazole fused heterocyclic derivatives were synthesized via a two-step procedure or a one-pot two step method, and their catalytic DNA cleavage abilities and anti-BVDV activities were also evaluated. The results obtained indicated that compounds 3b-3c could catalyze the cleavage of supercoiled DNA (pUC 19 plasmid DNA) to nicked DNA under physiological conditions with high yields via a hydrolytic mechanism. The studies on anti-viral activities against bovine viral diarrhea virus (BVDV) demonstrated that some of the pyrazole derivatives showed pronounced anti-BVDV activity with interesting ECso values and no significant cytotoxicity. Among them, compound 31 showed the highest antiviral activity (ECso = 0.12 μmol/L) and was 10 fold more than that of the positive control ribavirin (ECso = 1.3 μmol/L), which provided a potential candidate for the development of anti-BVDV agents.
基金financially supported by the National Natural Science Foundation of China (Nos.31171877,31571991,21372132)the International Science & Technology Cooperation Program of China (No.2014DFR41030)
文摘A series of novel N-(3-furan-2-yl-l-phenyl-lH-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis (L) Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.