N-(2-oxo-2-(4-fluorophenyl)ethyl)-2-(5-bromo-2-methylphenyl)acetamide | 1240649-46-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-oxo-2-(4-fluorophenyl)ethyl)-2-(5-bromo-2-methylphenyl)acetamide
• 英文别名: 2-(5-bromo-2-methylphenyl)-N-[2-(4-fluorophenyl)-2-oxoethyl]acetamide
• CAS: 1240649-46-0
• 化学式: C₁₇H₁₅BrFNO₂
• 分子量: 364.214
• InChiKey: ALMRZMUSFIZVQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-oxo-2-(4-fluorophenyl)ethyl)-2-(5-bromo-2-methylphenyl)acetamide 在 劳森试剂 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以88.2%的产率得到2-(5-bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiazole
  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：

  2-(5-溴-2-甲基苯基)乙酸 、 2-氨基-4’-氟苯乙酮盐酸盐 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以62.4%的产率得到N-(2-oxo-2-(4-fluorophenyl)ethyl)-2-(5-bromo-2-methylphenyl)acetamide
  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

• Discovery of Canagliflozin, a Novel <i>C</i>-Glucoside with Thiophene Ring, as Sodium-Dependent Glucose Cotransporter 2 Inhibitor for the Treatment of Type 2 Diabetes Mellitus
  作者：Sumihiro Nomura、Shigeki Sakamaki、Mitsuya Hongu、Eiji Kawanishi、Yuichi Koga、Toshiaki Sakamoto、Yasuo Yamamoto、Kiichiro Ueta、Hirotaka Kimata、Keiko Nakayama、Minoru Tsuda-Tsukimoto

  DOI：10.1021/jm100332n

  日期：2010.9.9

  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.