Ethyl 2-hydroxy-2-(2-oxooxan-3-ylidene)acetate | 110977-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: Ethyl 2-hydroxy-2-(2-oxooxan-3-ylidene)acetate
• 英文别名: ethyl 2-hydroxy-2-(2-oxooxan-3-ylidene)acetate
• CAS: 110977-72-5
• 化学式: C₉H₁₂O₅
• 分子量: 200.191
• InChiKey: QXLVJJUNRSQXID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-hydroxy-2-(2-oxooxan-3-ylidene)acetate 在 盐酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 4,9-Dihydropyrano<3,4-b>indol-1(3H)-on
  参考文献：
  名称：

  Synthesis and Evaluations of GLP-1 Secretion and Anti-Diabetic Effect in KKAy Mice of New Tricyclic Compounds

  摘要：

  Glucagon-like peptide-1 (GLP-1), which belongs to the family of incretins, plays important role for the regulation of plasma glucose. Accordingly, GLP-1-based therapies for type 2 diabetes have recognized as one of the most interesting target. In this study, we have found the new tricyclic compounds having strong GLP-1 secretion from human intestinal L cells, and anti-diabetic properties in spontaneously obese and diabetic KKAy mice. The most potent compound 5ka was obtained as the unexpected product, and we would like to report the details of the synthesis, structure elucidations, pharmacological activities on secretion of GLP-1, and anti-diabetic effects using diabetic KKAy mice.

  DOI：

  10.3987/com-14-s(k)29

文献信息

• Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1
  作者：Daisuke Minehira、Daisuke Takeda、Hirokazu Urata、Atsushi Kato、Isao Adachi、Xu Wang、Yuji Matsuya、Kenji Sugimoto、Mayuko Takemura、Satoshi Endo、Toshiyuki Matsunaga、Akira Hara、Jun Koseki、Kayo Narukawa、Shuichi Hirono、Naoki Toyooka

  DOI：10.1016/j.bmc.2011.10.073

  日期：2012.1

  New substituted (1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 mu M) with clinically used epalrestat (IC50 = 0.1 mu M). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 mu M) and very high selectivity for AKR1B1 against AKR1A1 (311: 1) and AKR1B10 (253: 1) compared with epalrestat. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and Evaluations of GLP-1 Secretion and Anti-Diabetic Effect in KKAy Mice of New Tricyclic Compounds
  作者：Naoki Toyooka、Isao Adachi、Daisuke Minehira、Daisuke Takeda、Shota Miyawaki、Atsushi Kato、Akira Miyazaki、Ryuta Miyatake、Masahito Umezaki、Kyoko Miura、Yoshiro Kitahara、Kenji Sugimoto、Yuji Matsuya

  DOI：10.3987/com-14-s(k)29

  日期：——

  Glucagon-like peptide-1 (GLP-1), which belongs to the family of incretins, plays important role for the regulation of plasma glucose. Accordingly, GLP-1-based therapies for type 2 diabetes have recognized as one of the most interesting target. In this study, we have found the new tricyclic compounds having strong GLP-1 secretion from human intestinal L cells, and anti-diabetic properties in spontaneously obese and diabetic KKAy mice. The most potent compound 5ka was obtained as the unexpected product, and we would like to report the details of the synthesis, structure elucidations, pharmacological activities on secretion of GLP-1, and anti-diabetic effects using diabetic KKAy mice.