(2S,3R,4R,5S,6R)-2-(3-((4'-chloro-[1,1'-biphenyl]-4-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-2-(3-((4'-chloro-[1,1'-biphenyl]-4-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2S,3R,4R,5S,6R)-2-[3-[[4-(4-chlorophenyl)phenyl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₆H₂₇ClO₅
• 分子量: 454.95
• InChiKey: BKHQTHQVLTYSQR-RTJMFUJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-内酯 在 正丁基锂 、 三异丙基硅烷 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 四丁基氟化铵 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 57.67h， 生成 (2S,3R,4R,5S,6R)-2-(3-((4'-chloro-[1,1'-biphenyl]-4-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  C-Aryl glucoside SGLT2 inhibitors containing a biphenyl motif as potential anti-diabetic agents

  摘要：

  A series of highly active C-aryl glucoside SGLT2 inhibitors containing a biphenyl motif were designed and synthesized for biological evaluation. Among the compounds tested, compound 16l demonstrated high inhibitory activity against SGLT2 (IC50 = 1.9 nM) with an excellent pharmacokinetic profile. Further study indicated that the in vivo efficacy of compound 16l was comparable to that of dapagliflozin, suggesting that further development would be worthwhile. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.040

文献信息

• C-Aryl glucoside SGLT2 inhibitors containing a biphenyl motif as potential anti-diabetic agents
  作者：Yuyang Ding、Liufeng Mao、Dengfeng Xu、Hui Xie、Ling Yang、Hongjiang Xu、Wenjun Geng、Yong Gao、Chunguang Xia、Xiquan Zhang、Qingyi Meng、Donghai Wu、Junling Zhao、Wenhui Hu

  DOI：10.1016/j.bmcl.2015.05.040

  日期：2015.7

  A series of highly active C-aryl glucoside SGLT2 inhibitors containing a biphenyl motif were designed and synthesized for biological evaluation. Among the compounds tested, compound 16l demonstrated high inhibitory activity against SGLT2 (IC50 = 1.9 nM) with an excellent pharmacokinetic profile. Further study indicated that the in vivo efficacy of compound 16l was comparable to that of dapagliflozin, suggesting that further development would be worthwhile. (C) 2015 Elsevier Ltd. All rights reserved.