methyl (E)-3-(3,5-dimethoxyphenyl)-2-(4-(4-((Z)-(2,4-dioxothiazolidine-5-ylidene)methyl)phenoxy)phenyl)acrylate | 606932-80-3

• 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 (E)-3-(3,5-dimethoxyphenyl)-2-(4-(4-((Z)-(2,4-dioxothiazolidine-5-ylidene)methyl)phenoxy)phenyl)acrylate
• 英文别名: methyl (E)-3-(3,5-dimethoxyphenyl)-2-[4-[4-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]prop-2-enoate
• CAS: 606932-80-3
• 化学式: C₂₈H₂₃NO₇S
• 分子量: 517.559
• InChiKey: NQMQMUPVBGQKSM-LUWDBDBNSA-N

物化性质

• 熔点：
  106-108 °C
• 密度：
  1.338±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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 (E)-3-(3,5-dimethoxyphenyl)-2-(4-(4-((Z)-(2,4-dioxothiazolidine-5-ylidene)methyl)phenoxy)phenyl)acrylate 在 platinum on activated charcoal ammonium formate 作用下， 以 溶剂黄146 为溶剂， 反应 15.0h， 以64%的产率得到methyl (E)-3-(3,5-dimethoxyphenyl)-2-(4-(4-((2,4-dioxothiazolidin-5-yl)methyl)phenoxy)phenyl)acrylate
  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：

  3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid methyl ester 在 哌啶 、 sodium hydride 、 苯甲酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 23.0h， 生成 methyl (E)-3-(3,5-dimethoxyphenyl)-2-(4-(4-((Z)-(2,4-dioxothiazolidine-5-ylidene)methyl)phenoxy)phenyl)acrylate
  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

• 噻唑烷二酮衍生物以及包含其的药物组合物
  申请人：苏州泽璟生物制药股份有限公司

  公开号：CN112209896B

  公开（公告）日：2023-05-16

  本发明涉及噻唑烷二酮衍生物以及包含其的药物组合物。具体地，本发明化合物具有式(I)所示结构，其中各基团和取代基的定义如说明书中所述；本发明还公开了所述化合物作为过氧化物酶体增殖剂激活受体(PPAR)激动剂的用途，具体如用于预防和/或治疗非酒精性脂肪肝炎以及相关的疾病的用途。
• 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。
• [EN] THIAZOLIDINEDIONE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME<br/>[FR] DÉRIVÉ DE THIAZOLIDINEDIONE ET COMPOSITION PHARMACEUTIQUE LE COMPRENANT<br/>[ZH] 噻唑烷二酮衍生物以及包含其的药物组合物
  申请人：SUZHOU ZELGEN BIOPHARMACEUTICALS CO LTD

  公开号：WO2021004487A1

  公开（公告）日：2021-01-14

  具有式(I)所示结构的噻唑烷二酮衍生物以及包含其的药物组合物，其中各基团和取代基的定义如说明书中所述。所述化合物作为过氧化物酶体增殖剂激活受体(PPAR)激动剂的用途，具体如用于预防和/或治疗非酒精性脂肪肝炎以及相关的疾病的用途。
• NOVEL HETEROCYCLIC ANALOGS OF DIPHENYLETHYLENE COMPOUNDS
  申请人：Theracos, Inc.

  公开号：EP1360178B1

  公开（公告）日：2009-02-18
• US7202366B2
  申请人：——

  公开号：US7202366B2

  公开（公告）日：2007-04-10