5-<(2-benzyl-3,4-dihydro-2H-1-benzopyran-6-yl)methylene>thiazolidine-2,4-dione | 109208-74-4

• 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-<(2-benzyl-3,4-dihydro-2H-1-benzopyran-6-yl)methylene>thiazolidine-2,4-dione
• 英文别名: 5-[(2-benzyl-3,4-dihydro-2H-1-benzopyran-6-yl)methylene]thiazolidine-2,4-dione；(5E)-5-[(2-benzyl-3,4-dihydro-2H-chromen-6-yl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 109208-74-4；109208-75-5；109229-59-6
• 化学式: C₂₀H₁₇NO₃S
• 分子量: 351.426
• InChiKey: LPSDRJKNQGNYAT-LDADJPATSA-N

物化性质

• 熔点：
  183-184 °C
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-<(2-benzyl-3,4-dihydro-2H-1-benzopyran-6-yl)methylene>thiazolidine-2,4-dione 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以57%的产率得到恩格列酮
  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-benzyl-6-formyl-3,4-dihydro-2H-1-benzopyran 在 sodium acetate 作用下， 反应 0.42h， 以83%的产率得到5-<(2-benzyl-3,4-dihydro-2H-1-benzopyran-6-yl)methylene>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

• J. Med. Chem. 1991, 34, 319-325
  作者：

  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.
• [EN] THIAZOLIDINE AND OXAZOLIDINE DERIVATIVES FOR THE TREATMENT OF ACUTE MYOCARDIAL INFARCTION AND INHIBITION OF CARDIOMYOCYTE APOPTOSIS<br/>[FR] DERIVES DE THIAZOLIDINE ET D'OXAZOLIDINE POUR LE TRAITEMENT D'INFARCTUS DU MYOCARDE AIGUS ET POUR L'INHIBITION DE L'APOPTOSE DES CARDIOMYOCYTES
  申请人：REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：WO1999059586A1

  公开（公告）日：1999-11-25

  (EN) It has been demonstrated that antidiabetic thiazolidine and oxazolidine derivatives (glitazones) exhibit novel effects on apoptosis of cardiomyocytes. These substances are capable of greatly decreasing apoptosis by a pathway that is not Caspase 3 dependent. Addition of IGF1 to the treatment further prevents apoptosis. Glitazones alone or glitazones plus IGF1 should be administered at the beginning of a myocardial infarction and continued through the recuperation period to reduce morbidity and prevent unfavorable remodeling of the myocardium.(FR) Il a été démontré que des dérivés antidiabétiques de thiazolidine et d'oxazolidine (glitazones) produisent de nouveaux effets sur l'apoptose des cardiomyocytes. Ces substances sont capables de diminuer fortement l'apoptose au moyen d'un processus qui n'est pas dépendant de Caspase 3. L'ajout de IGF1 contribue à freiner l'apoptose. Il est recommandé d'administrer, au commencement d'un infarctus du myocarde, des glitazones seules ou des glitazones plus IGF1 et de continuer ce traitement pendant la convalescence, de manière à réduire l'état pathologique et à empêcher un remodelage défavorable du myocarde.