methyl 3-(3,5-dimethoxyphenyl)-2-[4-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate | 606932-84-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 3-(3,5-dimethoxyphenyl)-2-[4-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate
• CAS: 606932-84-7
• 化学式: C₂₈H₂₅NO₇S
• 分子量: 519.575
• InChiKey: JXPMQUGRKBWQFX-MYYYXRDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-(3,5-dimethoxyphenyl)-2-[4-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 25.0 ℃ 、448.16 kPa 条件下， 反应 52.0h， 以38%的产率得到3-(3,5-dimethoxy-phenyl)-2-{4-[4-(2,4-dioxo-thiazolidin-5-ylmethyl)-phenoxy]-phenyl}-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and structure–Activity relationship studies of cinnamic acid-based novel thiazolidinedione antihyperglycemic agents

  摘要：

  A number of 2,4-thiazolidinedione derivatives of -phenyl substituted cinnamic acid were synthesized and studied for their PPAR agonist activity. The E-isomer of cinnamic acid, 11, showed moderate PPAR transactivation. The corresponding Z-isomer, 23, and double bond reduced derivative, 15, were found to be much less potent. Although the E-isomer showed a moderate PPARgamma transactivation, it demonstrated a strong glucose-lowering effect in a genetic rodent model of diabetes. Results of pharmacokinetic, metabolism and permeability studies are consistent with 11 being an active prodrug with an active metabolite, 14, that has similar glucose lowering and PPARgamma agonist properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00393-6
• 作为产物：
  描述：

  对羟基苯乙酸 在 palladium on activated charcoal 哌啶 、 硫酸 、 氢气 、 乙酸酐 、 sodium hydride 、 三乙胺 、 苯甲酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 64.0h， 生成 methyl 3-(3,5-dimethoxyphenyl)-2-[4-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate
  参考文献：
  名称：

  Synthesis and structure–Activity relationship studies of cinnamic acid-based novel thiazolidinedione antihyperglycemic agents

  摘要：

  A number of 2,4-thiazolidinedione derivatives of -phenyl substituted cinnamic acid were synthesized and studied for their PPAR agonist activity. The E-isomer of cinnamic acid, 11, showed moderate PPAR transactivation. The corresponding Z-isomer, 23, and double bond reduced derivative, 15, were found to be much less potent. Although the E-isomer showed a moderate PPARgamma transactivation, it demonstrated a strong glucose-lowering effect in a genetic rodent model of diabetes. Results of pharmacokinetic, metabolism and permeability studies are consistent with 11 being an active prodrug with an active metabolite, 14, that has similar glucose lowering and PPARgamma agonist properties. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00393-6

文献信息

• Novel heterocyclic analogs of diphenylethylene compounds
  申请人：Neogi Partha

  公开号：US20080293949A1

  公开（公告）日：2008-11-27

  Novel diphenylethylene compounds and derivatives thereof containing thiazolidinedione or oxazolidinedione moieties are provided which are effective in lowering blood glucose level, serum insulin, triglyceride and free fatty acid levels in animal models of Type II diabetes. The compounds are disclosed as useful for a variety of treatments including the treatment of inflammation, inflammatory and immunological diseases, insulin resistance, hyperlipidemia, coronary artery disease, cancer and multiple sclerosis.

  提供了含有噻唑烷二酮或噁唑烷二酮基团的新型二苯乙烯化合物及其衍生物，这些化合物在2型糖尿病动物模型中有效降低血糖水平、血清胰岛素、甘油三酯和游离脂肪酸水平。这些化合物被披露为用于各种治疗，包括治疗炎症、炎症和免疫性疾病、胰岛素抵抗、高脂血症、冠状动脉疾病、癌症和多发性硬化症。
• US7202366B2
  申请人：——

  公开号：US7202366B2

  公开（公告）日：2007-04-10
• US7407978B2
  申请人：——

  公开号：US7407978B2

  公开（公告）日：2008-08-05
• US7718682B2
  申请人：——

  公开号：US7718682B2

  公开（公告）日：2010-05-18