Ethyl 1-[2-(4-formylphenoxy)ethyl]-1H-indole-2-carboxylate | 205371-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Ethyl 1-[2-(4-formylphenoxy)ethyl]-1H-indole-2-carboxylate
• 英文别名: ethyl 1-[2-(4-formylphenoxy)ethyl]indole-2-carboxylate
• CAS: 205371-44-4
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: QRKHAMSLOABKHS-UHFFFAOYSA-N

物化性质

• 沸点：
  541.4±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 1-[2-(4-formylphenoxy)ethyl]-1H-indole-2-carboxylate 在 哌啶 、 氢氧化钾 、 苯甲酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 2.0h， 生成 1-[2-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]ethyl]indole-2-carboxylic acid
  参考文献：
  名称：

  Novel Euglycemic and Hypolipidemic Agents. 1

  摘要：

  A series of [[(heterocyclyl)ethoxy]benzyl]-2,4-thiazolidinediones have been synthesized by the condensation of corresponding aldehyde 1 and 2,4-thiazolidinedione followed by hydrogenation. Both unsaturated thiazolidinedione 2 and its saturated counterpart 3 have shown antihyperglycemic activity. Many of these compounds have shown superior euglycemic and hypolipidemic activity compared to troglitazone (CS 045). The indole analogue DRF-2189 (3g) was found to be a very potent insulin sensitizer, comparable to BRL-49653 in genetically obese C57BL/6J-ob/ob and 57BL/KsJ-db/db mice. Pharmacokinetic and tissue distribution studies conducted on BRL-49653 and DRF-2189 (3g) indicate that these drugs are well-distributed in target tissues. On the basis of euglycemic activity as well as enhanced selectivity against reduction of triglycerides in plasma, DRF-2189 (3g) has been selected for further evaluation.

  DOI：

  10.1021/jm970444e
• 作为产物：
  描述：

  吲哚-2-羧酸乙酯 、 4-(2-溴乙氧基)苯甲醛 在 potassium carbonate 作用下， 生成 Ethyl 1-[2-(4-formylphenoxy)ethyl]-1H-indole-2-carboxylate
  参考文献：
  名称：

  Novel Euglycemic and Hypolipidemic Agents. 1

  摘要：

  A series of [[(heterocyclyl)ethoxy]benzyl]-2,4-thiazolidinediones have been synthesized by the condensation of corresponding aldehyde 1 and 2,4-thiazolidinedione followed by hydrogenation. Both unsaturated thiazolidinedione 2 and its saturated counterpart 3 have shown antihyperglycemic activity. Many of these compounds have shown superior euglycemic and hypolipidemic activity compared to troglitazone (CS 045). The indole analogue DRF-2189 (3g) was found to be a very potent insulin sensitizer, comparable to BRL-49653 in genetically obese C57BL/6J-ob/ob and 57BL/KsJ-db/db mice. Pharmacokinetic and tissue distribution studies conducted on BRL-49653 and DRF-2189 (3g) indicate that these drugs are well-distributed in target tissues. On the basis of euglycemic activity as well as enhanced selectivity against reduction of triglycerides in plasma, DRF-2189 (3g) has been selected for further evaluation.

  DOI：

  10.1021/jm970444e

文献信息

• Novel Euglycemic and Hypolipidemic Agents. 1
  作者：Braj B. Lohray、Vidya Bhushan、Bheema P. Rao、Gurram R. Madhavan、Nagabelli Murali、Krovvidi N. Rao、Ananth K. Reddy、Bagepalli M. Rajesh、Pamulapati G. Reddy、Ranjan Chakrabarti、Reeba K. Vikramadithyan、Ramanujam Rajagopalan、Rao N. V. S. Mamidi、Hemant K. Jajoo、Swaminathan Subramaniam

  DOI：10.1021/jm970444e

  日期：1998.5.1

  A series of [[(heterocyclyl)ethoxy]benzyl]-2,4-thiazolidinediones have been synthesized by the condensation of corresponding aldehyde 1 and 2,4-thiazolidinedione followed by hydrogenation. Both unsaturated thiazolidinedione 2 and its saturated counterpart 3 have shown antihyperglycemic activity. Many of these compounds have shown superior euglycemic and hypolipidemic activity compared to troglitazone (CS 045). The indole analogue DRF-2189 (3g) was found to be a very potent insulin sensitizer, comparable to BRL-49653 in genetically obese C57BL/6J-ob/ob and 57BL/KsJ-db/db mice. Pharmacokinetic and tissue distribution studies conducted on BRL-49653 and DRF-2189 (3g) indicate that these drugs are well-distributed in target tissues. On the basis of euglycemic activity as well as enhanced selectivity against reduction of triglycerides in plasma, DRF-2189 (3g) has been selected for further evaluation.