5-[2-(4-Benzyloxy-benzyl)-chroman-6-ylmethyl]-thiazolidine-2,4-dione | 120355-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-[2-(4-Benzyloxy-benzyl)-chroman-6-ylmethyl]-thiazolidine-2,4-dione
• 英文别名: 5-[[2-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 120355-95-5
• 化学式: C₂₇H₂₅NO₄S
• 分子量: 459.566
• InChiKey: MMRAKHZTDKTXGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[2-(4-Benzyloxy-benzyl)-chroman-6-ylmethyl]-thiazolidine-2,4-dione 在 氢溴酸 、 溶剂黄146 作用下， 反应 1.5h， 以35%的产率得到5-<(2-(4-hydroxybenzyl)-3,4-dihydro-2H-1-benzopyran-6-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
• 作为产物：
  描述：

  (5Z)-5-[[2-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromen-6-yl]methylidene]-1,3-thiazolidine-2,4-dione 生成 5-[2-(4-Benzyloxy-benzyl)-chroman-6-ylmethyl]-thiazolidine-2,4-dione
  参考文献：
  名称：

  CLARK, DAVID A.

  摘要：

  DOI：

文献信息

• Thiazolidinediones as hypoglycemic and anti-atherosclerosis agents
  申请人：PFIZER INC.

  公开号：EP0319189A1

  公开（公告）日：1989-06-07

  The present invention relates to compounds of the formula wherein the broken line is an optional bond, and the pharmaceutically acceptable cationic salts thereof, having utility as hypoglycemic and anti-atherosclerosis agents, and pharmaceutical compositions containing them.

  本发明涉及如下式的化合物 其中断线为任选键的化合物及其药学上可接受的阳离子盐，它们具有降血糖和抗动脉粥样硬化的作用，以及含有它们的药物组合物。
• CLARK, DAVID A.
  作者：CLARK, DAVID A.

  DOI：——

  日期：——
• US4791125A
  申请人：——

  公开号：US4791125A

  公开（公告）日：1988-12-13
• Substituted dihydrobenzopyran and dihydrobenzofuran thiazolidine-2,4-diones as hypoglycemic agents
  作者：David A. Clark、Steven W. Goldstein、Robert A. Volkmann、James F. Eggler、Gerald F. Holland、Bernard Hulin、Ralph W. Stevenson、David K. Kreutter、E. Michael Gibbs

  DOI：10.1021/jm00105a050

  日期：1991.1

  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.