5-(3-Benzyl-2,3-dihydro-benzofuran-5-ylmethyl)-thiazolidine-2,4-dione | 109209-25-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 5-(3-Benzyl-2,3-dihydro-benzofuran-5-ylmethyl)-thiazolidine-2,4-dione
• 英文别名: 5-[(3-Benzyl-2,3-dihydro-1-benzofuran-5-yl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 109209-25-8
• 化学式: C₁₉H₁₇NO₃S
• 分子量: 339.415
• InChiKey: PGMCPWITEFNWAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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：

  3-benzyl-2,3-dihydro-l-benzofuran-5-carbaldehyde 在 palladium on activated charcoal 氢气 、 sodium acetate 、 溶剂黄146 作用下， 25.0~140.0 ℃ 、6.67 kPa 条件下， 反应 0.42h， 生成 5-(3-Benzyl-2,3-dihydro-benzofuran-5-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