5-[2-(4-Methoxy-benzyl)-chroman-6-ylmethyl]-thiazolidine-2,4-dione | 131194-49-5

• 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-Methoxy-benzyl)-chroman-6-ylmethyl]-thiazolidine-2,4-dione
• 英文别名: 5-[[2-[(4-methoxyphenyl)methyl]-3,4-dihydro-2H-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 131194-49-5
• 化学式: C₂₁H₂₁NO₄S
• 分子量: 383.468
• InChiKey: LMLLLSOVMLYKFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-[1-[2-(4-Methoxy-benzyl)-chroman-6-yl]-meth-(E)-ylidene]-thiazolidine-2,4-dione 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以83%的产率得到5-[2-(4-Methoxy-benzyl)-chroman-6-ylmethyl]-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

• 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.