A series of gem-dimethyl-bearing C-glucosides were designed and synthesized as SGLT2 inhibitors,with anhydrous aluminum chloride-mediated Friedel-Crafts alkylation to construct the gem-dimethyl functionality being the...A series of gem-dimethyl-bearing C-glucosides were designed and synthesized as SGLT2 inhibitors,with anhydrous aluminum chloride-mediated Friedel-Crafts alkylation to construct the gem-dimethyl functionality being the key step.The in vivo anti-hyperglycemic activity was evaluated with mice oral glucose tolerance test（OGTT）,and all the synthesized compounds showed significant but less potent anti-hyperglycemic activity than the positive control dapagliflozin.展开更多
Three novel gem-dimethyl C-glucosides were designed as sodium-glucose co-transporter 2 （SGLT2） inhibitors, and their syntheses started from D-glucose and three 2-substituted-5-bromobenzoic acids were achieved via a ...Three novel gem-dimethyl C-glucosides were designed as sodium-glucose co-transporter 2 （SGLT2） inhibitors, and their syntheses started from D-glucose and three 2-substituted-5-bromobenzoic acids were achieved via a facile 8-step protocol, with the key step being anhydrous aluminum chloride-catalyzed Friedel-Crafts alkylation of tertiary alcohols and phenetol. These three SGLT2 inhibitors were evaluated in vivo with a mice oral glucose tolerance test （OGTT）, and the anti-hyperglycemic activities of all these three compounds were comparable with that of the positive control Dapagliflozin.展开更多
The title compound was synthesized and its crystal structure was determined by single-crystal X-ray diffraction.The crystal is of monoclinic system（C31H37ClO10,Mr = 605.06）,space group P21 with a = 11.882（5）,b = 1...The title compound was synthesized and its crystal structure was determined by single-crystal X-ray diffraction.The crystal is of monoclinic system（C31H37ClO10,Mr = 605.06）,space group P21 with a = 11.882（5）,b = 10.106（5）,c = 13.816（6）,V = 1545.9（12）（A°）^3,Z = 2,Dc = 1.300 g/cm^3,F（000） = 640,μ = 0.179 mm^-1,the final R = 0.0430 and wR = 0.0595 for 4960 observed reflections（I 〉 2σ（I））.The title compound was confirmed to be a β-anomer by single-crystal X-ray diffraction and 1H NMR.The proximal benzene ring is nearly orthogonal to the glucopyranoside ring,and the two benzene rings are also almost orthogonal to each other.Four non-classical intermolecular hydrogen bonds observed in the crystal lattice help to stabilize the crystal.展开更多
基金Key Projects of Tianjin Science and Technology Support Plan(No. 10ZCKFSH01300) for financial support
文摘A series of gem-dimethyl-bearing C-glucosides were designed and synthesized as SGLT2 inhibitors,with anhydrous aluminum chloride-mediated Friedel-Crafts alkylation to construct the gem-dimethyl functionality being the key step.The in vivo anti-hyperglycemic activity was evaluated with mice oral glucose tolerance test（OGTT）,and all the synthesized compounds showed significant but less potent anti-hyperglycemic activity than the positive control dapagliflozin.
文摘Three novel gem-dimethyl C-glucosides were designed as sodium-glucose co-transporter 2 （SGLT2） inhibitors, and their syntheses started from D-glucose and three 2-substituted-5-bromobenzoic acids were achieved via a facile 8-step protocol, with the key step being anhydrous aluminum chloride-catalyzed Friedel-Crafts alkylation of tertiary alcohols and phenetol. These three SGLT2 inhibitors were evaluated in vivo with a mice oral glucose tolerance test （OGTT）, and the anti-hyperglycemic activities of all these three compounds were comparable with that of the positive control Dapagliflozin.
基金Supported by Key Projects of Tianjin Science and Technology Support Plan (10ZCKFSH01300)
文摘The title compound was synthesized and its crystal structure was determined by single-crystal X-ray diffraction.The crystal is of monoclinic system（C31H37ClO10,Mr = 605.06）,space group P21 with a = 11.882（5）,b = 10.106（5）,c = 13.816（6）,V = 1545.9（12）（A°）^3,Z = 2,Dc = 1.300 g/cm^3,F（000） = 640,μ = 0.179 mm^-1,the final R = 0.0430 and wR = 0.0595 for 4960 observed reflections（I 〉 2σ（I））.The title compound was confirmed to be a β-anomer by single-crystal X-ray diffraction and 1H NMR.The proximal benzene ring is nearly orthogonal to the glucopyranoside ring,and the two benzene rings are also almost orthogonal to each other.Four non-classical intermolecular hydrogen bonds observed in the crystal lattice help to stabilize the crystal.
