3-benzyl-2,3-dihydro-l-benzofuran-5-carbaldehyde | 109209-65-6

• 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: 3-benzyl-2,3-dihydro-l-benzofuran-5-carbaldehyde
• 英文别名: 3-benzyl-2,3-dihydro-1-benzofuran-5-carbaldehyde
• CAS: 109209-65-6
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: CYIQNPRKSVDNCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  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

文献信息

• Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders
  申请人：Newron Pharmaceuticals S.p.A.

  公开号：EP1557166A1

  公开（公告）日：2005-07-27

  Methods of using certain α-aminoamide derivatives to treat lower urinary tract disorders. The therapeutic agents of the invention are able to reduce or even stop the lower urinary tract disorders substantially without side effects.

  使用某些α-氨基酰胺衍生物的方法来治疗下尿路障碍。该发明的治疗剂能够在没有副作用的情况下显著减少甚至停止下尿路障碍。
• Alpha-Aminoamide Derivatives Useful in the Treatment of Lower Urinary Tract Disorders
  申请人：Barbanti Elena

  公开号：US20080132567A1

  公开（公告）日：2008-06-05

  Methods of using certain α-aminoamide derivatives to treat lower urinary tract disorders. The therapeutic agents of the invention are able to reduce or even stop the lower urinary tract disorders substantially without side effects.

  使用某些α-氨基酰胺衍生物来治疗下尿路障碍的方法。本发明的治疗剂能够在几乎没有副作用的情况下显著减轻甚至停止下尿路障碍。
• Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders
  申请人：Newron Pharmaceuticals S.p.A.

  公开号：US07718815B2

  公开（公告）日：2010-05-18

  Methods of using certain α-aminoamide derivatives to treat lower urinary tract disorders. The therapeutic agents of the invention are able to reduce or even stop the lower urinary tract disorders substantially without side effects.

  使用某些α-氨基酰胺衍生物的方法治疗下尿路障碍。本发明的治疗剂能够大大减少甚至停止下尿路障碍，且无副作用。
• US7718815B2
  申请人：——

  公开号：US7718815B2

  公开（公告）日：2010-05-18
• [EN] ALPHA-AMINOAMIDE DERIVATIVES USEFUL IN THE TREATMENT OF LOWER URINARY TRACT DISORDERS<br/>[FR] DERIVES D'ALPHA-AMINOAMIDE QUI CONVIENNENT POUR LE TRAITEMENT DES TROUBLES DES VOIES URINAIRES INFERIEURES
  申请人：NEWRON PHARM SPA

  公开号：WO2005070405A1

  公开（公告）日：2005-08-04

  Methods of using certain α-aminoamide derivatives to treat lower urinary tract disorders. The therapeutic agents of the invention are able to reduce or even stop the lower urinary tract disorders substantially without side effects.