spiro(6-formyl-3,4-dihydro-2H-1-benzopyran-2,1'-cyclopentane) | 131194-63-3

• 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: spiro(6-formyl-3,4-dihydro-2H-1-benzopyran-2,1'-cyclopentane)
• 英文别名: Spiro[3,4-dihydrochromene-2,1'-cyclopentane]-6-carbaldehyde
• CAS: 131194-63-3
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: PSFDZHXJELENCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro(6-formyl-3,4-dihydro-2H-1-benzopyran-2,1'-cyclopentane) 在 palladium on activated charcoal 氢气 、 sodium acetate 、 溶剂黄146 作用下， 25.0~140.0 ℃ 、344.73 kPa 条件下， 反应 0.42h， 生成 5-(Spiro[3,4-dihydrochromene-2,1'-cyclopentane]-6-ylmethyl)-1,3-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：

  螺[2H-1-苯并吡喃-2,1-环戊并n]-4(3h)-酮 在 palladium on activated charcoal 盐酸 、 氢气 、 三氯氧磷 作用下， 25.0~80.0 ℃ 、344.73 kPa 条件下， 反应 5.5h， 生成 spiro(6-formyl-3,4-dihydro-2H-1-benzopyran-2,1'-cyclopentane)
  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.