5-<(2-(4-hydroxybenzyl)-3,4-dihydro-2H-1-benzopyran-6-yl)methyl>thiazolidine-2,4-dione | 131194-41-7

• 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-hydroxybenzyl)-3,4-dihydro-2H-1-benzopyran-6-yl)methyl>thiazolidine-2,4-dione
• 英文别名: 5-[[2-[(4-hydroxyphenyl)methyl]-3,4-dihydro-2H-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 131194-41-7
• 化学式: C₂₀H₁₉NO₄S
• 分子量: 369.441
• InChiKey: FWRGMNJCWPVFBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (5E)-5-[[2-[(4-phenylmethoxyphenyl)methyl]-3,4-dihydro-2H-chromen-6-yl]methylidene]-1,3-thiazolidine-2,4-dione 在 palladium on activated charcoal 氢溴酸 、 氢气 、 溶剂黄146 作用下， 25.0 ℃ 、344.73 kPa 条件下， 反应 1.5h， 生成 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

文献信息

• 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：——
• 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.