2-Benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde | 109209-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-Benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde
• CAS: 109209-62-3
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: UOFKHRIVBXKNNM-UHFFFAOYSA-N

物化性质

• 沸点：
  396.2±21.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  2-Benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde 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-[(2-benzyl-2,3-dihydrobenzofuran-5-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：——
• Hypoglycemic thiazolidinediones
  申请人：PFIZER INC.

  公开号：EP0207605B1

  公开（公告）日：1990-02-07
• US4703052A
  申请人：——

  公开号：US4703052A

  公开（公告）日：1987-10-27
• [EN] HYPOGLYCEMIC THIAZOLIDINEDIONES
  申请人：PFIZER INC.

  公开号：WO1986007056A1

  公开（公告）日：1986-12-04

  (EN) Hypoglycemic 2,3-dihydro-5-benzo¨ADb¨BDfuranyl-2,3-dihydro-5-benzo¨ADb¨BDthienyl-, 3,4-dihydro(2H)-6-benzo-pyranyl- and 6-thiochromanyl-thiazolidine-2,4-diones and pharmaceutically acceptable salts thereof, method for their use in treatment of hyperglycemic animals and pharmaceutical compositions containing them.(FR) Thiazolidine-2,4-diones hypoglycémique de 2,3-dihydro-5-benzo¨ADb¨BDfuranyl-2,3-dihydro-5-benzo¨ADb¨BDthiényle, de 3,4-dihydro(2h)-6-benzo-pyranyle et de 6-thiochromanyle et sels acceptables pharmaceutiquement à partir desdits composés, ainsi que méthode d'utilisation desdits composés pour le traitement d'hyperglycémie chez les animaux et compositions pharmaceutiques contenant lesdits composés.
• 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.