5-[[4-[2-(1-indolyl)ethoxy]phenyl]methylene]thiazolidine-2,4-dione

• 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: 5-[[4-[2-(1-indolyl)ethoxy]phenyl]methylene]thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[4-(2-indol-1-ylethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₂₀H₁₆N₂O₃S
• 分子量: 364.425
• InChiKey: MZKMQFJQCKWJRD-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[[4-[2-(1-indolyl)ethoxy]phenyl]methylene]thiazolidine-2,4-dione 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 以92%的产率得到5-[[4-(2-吲哚-1-基乙氧基)苯基]甲基]-1,3-噻唑烷-2,4-二酮
  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：

  4-(2-溴乙氧基)苯甲醛 在 哌啶 、 sodium amide 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 5-[[4-[2-(1-indolyl)ethoxy]phenyl]methylene]thiazolidine-2,4-dione
  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 indole containing thiazolidinedione derivatives as potent euglycemic and hypolipidaemic agents
  作者：Braj B. Lohray、V. Bhushan、P.Bheema Rao、G.R. Madhavan、N. Murali、K.Narasimha Rao、G.R. Madhavan、N. Murali、K.Narasimha Rao、K. Anantha Reddy、B.M. Rajesh、P. Ganpathy Reddy、R. Chakrabarti、R. Rajagopalan

  DOI：10.1016/s0960-894x(97)00118-2

  日期：1997.1

  Several thiazolidinediones having indol as heterocyclic moiety have been synthesized and evaluated for euglycemic properties. A few of them have been found to be superior to troglitazone. (C) 1997 Elsevier Science Ltd.
• 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.