5-[1-(2-Cyclohexylmethyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione | 109209-03-2

• 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-[1-(2-Cyclohexylmethyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione
• CAS: 109209-03-2
• 化学式: C₂₀H₂₃NO₃S
• 分子量: 357.474
• InChiKey: KBAIYOGVUVCMFT-LDADJPATSA-N

物化性质

• 密度：
  1.263±0.06 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  5-[1-(2-Cyclohexylmethyl-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88%的产率得到5-(2-Cyclohexylmethyl-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
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 2-Cyclohexylmethyl-chroman-6-carbaldehyde 在 sodium acetate 作用下， 反应 0.42h， 以44%的产率得到5-[1-(2-Cyclohexylmethyl-chroman-6-yl)-meth-(E)-ylidene]-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