(3-Bromophenyl)-(5-ethylthiophen-2-yl)methanone | 1094458-06-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-Bromophenyl)-(5-ethylthiophen-2-yl)methanone
• CAS: 1094458-06-6
• 化学式: C₁₃H₁₁BrOS
• 分子量: 295.2
• InChiKey: OXGIEAPWYIMSMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-Bromophenyl)-(5-ethylthiophen-2-yl)methanone 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 (l)-3-bromo-(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：

  2-乙基噻吩 、 3-溴苯甲酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 (3-Bromophenyl)-(5-ethylthiophen-2-yl)methanone
  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.