5-hydroxy-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester | 853076-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 5-hydroxy-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 5-hydroxy-8-(3-methoxy-3-oxopropyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 853076-89-8
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: DTPCRQOQDXDKQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 在 sodium hydroxide 、 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 8-(2-carboxy-ethyl)-5-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid isobutyl ester
  参考文献：
  名称：

  Tetrahydroisoquinoline PPARγ agonists: Design of novel, highly selective non-TZD antihyperglycemic agents

  摘要：

  Novel tetrahydroisoquinolines have been developed as potent PPAR ligands. Evaluation of these compounds in PPAR gamma responsive models of type 2 diabetes is described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.028
• 作为产物：
  描述：

  5-羟基-1,2,3,4-四氢异喹啉 在 palladium on activated charcoal palladium diacetate 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 5-hydroxy-8-(2-methoxycarbonyl-ethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Tetrahydroisoquinoline PPARγ agonists: Design of novel, highly selective non-TZD antihyperglycemic agents

  摘要：

  Novel tetrahydroisoquinolines have been developed as potent PPAR ligands. Evaluation of these compounds in PPAR gamma responsive models of type 2 diabetes is described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.028

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS, USEFUL FOR THE TREATMENT AND/OR PREVENTION OF DISORDERS MODULATED BY A PPAR<br/>[FR] COMPOSES HETEROCYCLIQUES UTILISES COMME MODULATEURS DES RECEPTEURS ACTIVES PROLIFERATEURS DU PEROXYSOME (PPAR), UTILES DANS LE TRAITEMENT ET/OU LA PREVENTION DE TROUBLES MODULES PAR UN PPAR
  申请人：LILLY CO ELI

  公开号：WO2005051945A1

  公开（公告）日：2005-06-09

  The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

  本发明涉及一种式(I)的化合物，或其药学上可接受的盐、溶剂合物、水合物或立体异构体，该化合物在治疗或预防由过氧化物酶体增殖激活受体（PPAR）介导的疾病中具有用途，如X综合征、2型糖尿病、高血糖、高脂血症、肥胖、凝血障碍、高血压、动脉硬化以及与X综合征和心血管疾病相关的其他疾病。
• Heterocyclic Compounds As Modulators Of Peroxisome Proliferator Activated Receptors, Useful For The Treatment And/Or Prevention Of Disorders Modulated By A Ppar
  申请人：Henry James Robert

  公开号：US20080207685A1

  公开（公告）日：2008-08-28

  The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate, hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

  本发明涉及一种式为(I)的化合物，或其药学上可接受的盐、溶剂合物、水合物或立体异构体，该化合物用于治疗或预防由过氧化物酶体增殖激活受体（PPAR）介导的疾病，如X综合征、2型糖尿病、高血糖、高脂血症、肥胖症、凝血障碍、高血压、动脉硬化以及其他与X综合征和心血管疾病相关的疾病。
• HETEROCYCLIC COMPOUNDS AS MODULATORS OF PEROXISOME PROLIFERATOR ACTIVATED RECEPTORS, USEFUL FOR THE TREAMTMENT AND/OR PREVENTION OF DISORDERS MODULATED BY A PPAR
  申请人：ELI LILLY AND COMPANY

  公开号：EP1687299A1

  公开（公告）日：2006-08-09
• Tetrahydroisoquinoline PPARγ agonists: Design of novel, highly selective non-TZD antihyperglycemic agents
  作者：James R. Henry、Yihong Li、Alan M. Warshawsky、Joseph T. Brozinick、Eric D. Hawkins、Elizabeth A. Misener、Daniel A. Briere、Chahrzad Montrose-Rafizadeh、Richard W. Zink、Nathan P. Yumibe、Rose T. Ajamie、Brad Wilken、Viswanath Devanarayan

  DOI：10.1016/j.bmcl.2006.09.028

  日期：2006.12

  Novel tetrahydroisoquinolines have been developed as potent PPAR ligands. Evaluation of these compounds in PPAR gamma responsive models of type 2 diabetes is described. (c) 2006 Elsevier Ltd. All rights reserved.