5-[(2-benzyl-2,3-dihydrobenzofuran-5-yl)methyl]thiazolidine-2,4-dione | 109208-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-[(2-benzyl-2,3-dihydrobenzofuran-5-yl)methyl]thiazolidine-2,4-dione
• 英文别名: 5-[(2-Benzyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 109208-73-3
• 化学式: C₁₉H₁₇NO₃S
• 分子量: 339.415
• InChiKey: DTWCLKZUSOJSOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-[1-(2-Benzyl-2,3-dihydro-benzofuran-5-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以30%的产率得到5-[(2-benzyl-2,3-dihydrobenzofuran-5-yl)methyl]thiazolidine-2,4-dione
  参考文献：
  名称：

  Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents

  摘要：

  A series of dihydrobenzofuran and dihydrobenzopyran thiazolidine-2,4-diones (compounds 3-26) was synthesized from the corresponding aryl aldehydes 1 in two steps. These compounds represent conformationally restricted analogues of the novel hypoglycemic ciglitazone. The series was evaluated by hypoglycemic effects in vitro by measuring stimulation of 2-deoxyglucose uptake in L6 myocytes and stimulation of expression of the glucose transporter protein in 3T3-L1 adipocytes. In vivo hypoglycemic effects were evaluated in the genetically obese ob/ob mouse, and structure-activity relationships are discussed. On the basis of this in vivo potency, we have selected the 2(R)-benzylbenzopyran derivative to be further studied in a clinical setting.

  DOI：

  10.1021/jm00105a050

文献信息

• Composition for use in the treatment and prevention of hyperuricemia
  申请人：Sankyo Company Limited

  公开号：EP0919232A1

  公开（公告）日：1999-06-02

  Insulin sensitivity enhancers, such as troglitazone, have the ability to treat and/or prevent hyperuricemia and may thus be used for the therapy or prophylaxis of such diseases as gout, urinary calculus, hyperuricemic nephropathy and Lesch-Nyhan syndrome.

  曲格列酮等胰岛素敏感性增强剂具有治疗和/或预防高尿酸血症的能力，因此可用于痛风、尿路结石、高尿酸血症肾病和莱希-尼汉综合征等疾病的治疗或预防。
• REMEDY FOR AUTOIMMUNE DISEASES
  申请人：Sankyo Company, Limited

  公开号：EP0953355A1

  公开（公告）日：1999-11-03

  A preventive or therapeutic agent for autoimmune diseases (excluding type I diabetes) contaning an insulin resistance improving substance as an active ingredient.

  一种预防或治疗自身免疫性疾病（I 型糖尿病除外）的制剂，含有一种改善胰岛素抵抗的物质作为活性成分。
• CLARK, DAVID A.;GOLDSTEIN, STEVEN W.;VOLKMANN, ROBERT A.;EGGLER, JAMES F.+, J. MED. CHEM., 34,(1991) N, C. 319-325
  作者：CLARK, DAVID A.、GOLDSTEIN, STEVEN W.、VOLKMANN, ROBERT A.、EGGLER, JAMES F.+

  DOI：——

  日期：——
• Hypoglycemic thiazolidinediones
  申请人：PFIZER INC.

  公开号：EP0207605B1

  公开（公告）日：1990-02-07
• US4703052A
  申请人：——

  公开号：US4703052A

  公开（公告）日：1987-10-27