(3R,4S,5S,6R)-2-[3-[(5-ethylthiophen-2-yl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol | 842132-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R)-2-[3-[(5-ethylthiophen-2-yl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol
• CAS: 842132-48-3
• 化学式: C₂₀H₂₆O₆S
• 分子量: 394.489
• InChiKey: FOXPBOJTEWRVJK-QUIYGKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6R)-2-[3-[(5-ethylthiophen-2-yl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 1-(β-D-glucopyranosyl)-3-(5-ethyl-2-thienylmethyl)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
• 作为产物：
  描述：

  甲醇 、 (3R,4S,5R,6R)-2-[3-[(5-ethylthiophen-2-yl)methyl]phenyl]-3,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-2-ol 在 甲烷磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (3R,4S,5S,6R)-2-[3-[(5-ethylthiophen-2-yl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxyoxane-3,4,5-triol
  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

• GLUCOPYRANOSIDE COMPOUND
  申请人：NOMURA Sumihiro

  公开号：US20120258913A1

  公开（公告）日：2012-10-11

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物的公式：其中环A和环B是：(1) 环A是一个可选取代的不饱和单环杂环，环B是一个可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，(2) 环A是一个可选取代的苯环，环B是一个可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或(3) 环A是一个可选取代的不饱和融合杂双环，环B是独立的可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是一个碳原子或氮原子；Y是—(CH2)n—(n为1或2)；或其药学上可接受的盐或前药。
• NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST SODIUM-DEPENDANT TRANSPORTER
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP1651658B1

  公开（公告）日：2013-01-16
• US7943788B2
  申请人：——

  公开号：US7943788B2

  公开（公告）日：2011-05-17
• US8202984B2
  申请人：——

  公开号：US8202984B2

  公开（公告）日：2012-06-19
• US8222219B2
  申请人：——

  公开号：US8222219B2

  公开（公告）日：2012-07-17