2-{4-[4-(bromomethyl)phenoxy]phenyl}-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester | 606932-83-6

• 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: 2-{4-[4-(bromomethyl)phenoxy]phenyl}-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester
• 英文别名: methyl (E)-2-[4-[4-(bromomethyl)phenoxy]phenyl]-3-(3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 606932-83-6
• 化学式: C₂₅H₂₃BrO₅
• 分子量: 483.359
• InChiKey: WQMWNOCCXSPGBT-ZVHZXABRSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  587.7±50.0 °C(predicted)
• 密度：
  1.340±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{4-[4-(bromomethyl)phenoxy]phenyl}-3-(3,5-dimethoxyphenyl)acrylic acid methyl ester 在 sodium hydroxide 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 16.25h， 生成 3-(3,5-dimethoxyphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-acrylic acid
  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：

  E-3-(3,5-dimethoxy-phenyl)-2-(4-hydroxy-phenyl)-acrylic Acid 在 sodium tetrahydroborate 、 硫酸 、 三溴化磷 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 2-{4-[4-(bromomethyl)phenoxy]phenyl}-3-(3,5-dimethoxyphenyl)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。
• Compounds for treatment of inflammation, diabetes and related disorders
  申请人：——

  公开号：US20040097593A1

  公开（公告）日：2004-05-20

  Novel acyl urea, thiourea, carbamate, thiocarbamate and related compounds are provided which are effective in inhibiting the cytokine-mediated inflammatory response in cultured cells, in ameliorating bone destruction in an animal model of arthritis and in lowering blood glucose levels in animal models of Type II diabetes mellitus. The compounds are disclosed as useful for a variety of treatments including the treatment of diabetes mellitus, insulin resistance, inflammation, inflammatory diseases, immunological diseases and cancer.

  提供了一系列新型酰基脲、硫脲、氨基甲酸酯、硫代氨基甲酸酯及相关化合物，这些化合物在培养细胞中抑制细胞因子介导的炎症反应、改善动物关节炎模型中的骨破坏以及降低动物2型糖尿病模型中的血糖水平方面具有有效性。这些化合物可用于多种治疗，包括糖尿病、胰岛素抵抗、炎症、炎症性疾病、免疫疾病和癌症的治疗。
• COMPOUNDS FOR TREATMENT OF INFLAMMATION, DIABETES AND RELATED DISORDERS
  申请人：Neogi Partha

  公开号：US20070259961A9

  公开（公告）日：2007-11-08

  Novel acyl urea, thiourea, carbamate, thiocarbamate and related compounds are provided which are effective in inhibiting the cytokine-mediated inflammatory response in cultured cells, in ameliorating bone destruction in an animal model of arthritis and in lowering blood glucose levels in animal models of Type II diabetes mellitus. The compounds are disclosed as useful for a variety of treatments including the treatment of diabetes mellitus, insulin resistance, inflammation, inflammatory diseases, immunological diseases and cancer.

  提供了一系列新型酰基脲、硫脲、氨基甲酸酯、硫代氨基甲酸酯及相关化合物，这些化合物在培养细胞中抑制细胞因子介导的炎症反应、改善关节炎动物模型中的骨破坏和降低2型糖尿病动物模型中的血糖水平方面具有有效性。这些化合物被披露为用于多种治疗，包括糖尿病、胰岛素抵抗、炎症、炎症性疾病、免疫疾病和癌症的治疗。
• NOVEL HETEROCYCLIC ANALOGS OF DIPHENYLETHYLENE COMPOUNDS
  申请人：Theracos, Inc.

  公开号：EP1549625A1

  公开（公告）日：2005-07-06
• US7323496B2
  申请人：——

  公开号：US7323496B2

  公开（公告）日：2008-01-29