1-(β-D-glucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thiazolylmethyl)benzene | 1240649-43-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-glucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thiazolylmethyl)benzene
• 英文别名: (2S,3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiazol-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4R,5S,6R)-2-[3-[[5-(4-fluorophenyl)-1,3-thiazol-2-yl]methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1240649-43-7
• 化学式: C₂₃H₂₄FNO₅S
• 分子量: 445.512
• InChiKey: JBNBSNDURSYDIY-PHNZBSFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(1-methoxyglucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thiazolylmethyl)benzene 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 1-(β-D-glucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thiazolylmethyl)benzene
  参考文献：
  名称：

  Discovery of Canagliflozin, a Novel C-Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Cotransporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus

  摘要：

  We discovered that C-glucosides 4 bearing a heteroaromatic ring formed metabolically more stable inhibitors for sodium-dependent glucose cotransporter 2 (SGLT2) than the O-glucoside, 2 (T-1095). A novel thiophene derivative 4b-3 (canagliflozin) was a highly potent and selective SGLT2 inhibitor and showed pronounced anti-hyperglycemic effects in high-fat diet fed KK (HF-KK) mice.

  DOI：

  10.1021/jm100332n

文献信息

• Thiazole Derivatives as SGLT2 Inhibitors and Pharmaceutical Composition Comprising Same
  申请人：Lee Jinhwa

  公开号：US20130090298A1

  公开（公告）日：2013-04-11

  The present invention relates to a novel compound with thiazole ring having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney, and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly diabetes.

  本发明涉及一种新型含有噻唑环的化合物，具有对存在于肠和肾中的钠依赖性葡萄糖共转运体2（SGLT2）的抑制活性，以及包含该化合物作为活性成分的制药组合物，用于预防或治疗代谢性疾病，特别是糖尿病。
• US8586550B2
  申请人：——

  公开号：US8586550B2

  公开（公告）日：2013-11-19