(Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid methyl ester | 606932-85-8

• 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: (Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid methyl ester
• 英文别名: 2-[4-hydroxyphenyl]-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester；Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid methyl ester；methyl (Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)prop-2-enoate
• CAS: 606932-85-8
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: ORLWDFQMHQUCRE-YVLHZVERSA-N

物化性质

• 沸点：
  479.8±45.0 °C(predicted)
• 密度：
  1.213±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-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 3-(3,5-dimethoxyphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)phenoxy]phenyl}acrylic 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：

  3,5-二甲氧基苯甲醛 在 硫酸 、 乙酸酐 、 三乙胺 作用下， 反应 48.0h， 生成 (Z)-3-(3,5-dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic 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

文献信息

• Novel heterocyclic analogs of diphenylethylene compounds
  申请人：——

  公开号：US20030181494A1

  公开（公告）日：2003-09-25

  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.

  提供含有噻唑二酮或噁唑二酮基团的新型二苯乙烯化合物及其衍生物，对II型糖尿病动物模型中的降低血糖水平、血清胰岛素、甘油三酯和游离脂肪酸水平具有有效作用。这些化合物被披露为用于多种治疗，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、癌症和多发性硬化等。
• STILBENE DERIVATIVES AS PSTAT3/IL-6 INHIBITORS
  申请人：Rajagopal Sridharan

  公开号：US20100298402A1

  公开（公告）日：2010-11-25

  Described are novel compounds of the formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, intermediates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites, and prodrugs thereof. These novel compounds can inhibit pSTAT3/IL-6 and are useful as a therapeutic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, autoimmune diseases, skin diseases, infections, inflammation, etc.

  描述了公式（I）的新化合物，它们的衍生物、类似物、互变异构体、立体异构体、多型体、水合物、溶剂合物、中间体、药学上可接受的盐、药物组合物、代谢物和前药。这些新化合物可以抑制pSTAT3/IL-6，并且可用作治疗或改善细胞生长相关疾病的药物或缓解剂，如恶性肿瘤、自身免疫疾病、皮肤病、感染、炎症等。
• Heterocyclic analogs of diphenylethylene compounds
  申请人：Theracos, Inc.

  公开号：US07407978B2

  公开（公告）日：2008-08-05

  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.

  提供一种含有噻唑烷二酮或肟唑烷二酮基团的新型二苯乙烯化合物及其衍生物，对于2型糖尿病动物模型具有降低血糖水平、血清胰岛素、三酰甘油和游离脂肪酸水平的有效性。这些化合物可用于多种治疗，包括炎症、炎症和免疫性疾病、胰岛素抵抗、高脂血症、冠状动脉疾病、癌症和多发性硬化的治疗。
• NOVEL HETEROCYCLIC ANALOGS OF DIPHENYLETHYLENE COMPOUNDS
  申请人：Theracos, Inc.

  公开号：EP1549625A1

  公开（公告）日：2005-07-06
• US7407978B2
  申请人：——

  公开号：US7407978B2

  公开（公告）日：2008-08-05