(+/-)-6-(aminomethyl)-5,6,7,8-tetrahydroquinazoline | 444199-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+/-)-6-(aminomethyl)-5,6,7,8-tetrahydroquinazoline
• 英文别名: 5,6,7,8-Tetrahydroquinazolin-6-ylmethanamine
• CAS: 444199-09-1
• 化学式: C₉H₁₃N₃
• 分子量: 163.222
• InChiKey: FHQNCERMMZSOBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [3-[(苄基磺酰基)氨基]-6-甲基-2-氧代-1,2-二氢吡啶基]乙酸 、 (+/-)-6-(aminomethyl)-5,6,7,8-tetrahydroquinazoline 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(6-Methyl-2-oxo-3-phenylmethanesulfonylamino-2H-pyridin-1-yl)-N-(5,6,7,8-tetrahydro-quinazolin-6-ylmethyl)-acetamide
  参考文献：
  名称：

  Selective 3-Amino-2-pyridinone acetamide thrombin inhibitors incorporating weakly basic partially saturated heterobicyclic P1-Arginine mimetics

  摘要：

  Novel, highly selective and potent thrombin inhibitors were identified as a result of combing the 3-benzylsulfonylamino-2-pyridinone acetamide P-2-P-3 surrogate with weakly basic partially saturated heterobicyclic P-1-arginine mimetics 1-8. The design, synthesis. biological activity, and the binding modes of non-covalent thrombin inhibitors featuring P-1-4,5,6,7-tetrahydroindazole, 5,6,7,8-tetrahydroquinazoline, and 4,5,6,7-tetrahydrobenzothiazole moieties are described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00717-0
• 作为产物：
  描述：

  4-氰基环己酮缩乙二醇 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 甲酸 、 水 、 sodium ethanolate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 甲苯 为溶剂， 反应 44.0h， 生成 (+/-)-6-(aminomethyl)-5,6,7,8-tetrahydroquinazoline
  参考文献：
  名称：

  A general synthetic approach to novel conformationally restricted arginine side chain mimetics

  摘要：

  A general synthesis of several novel partially saturated, conformationally restricted heterobicyclic arginine side chain mimetics is described. These compounds are interesting peptidomimetic building blocks for incorporation into trypsin-like serine protease inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01243-1

文献信息

• Thrombin inhibitors
  申请人：Marsic Peterlin Lucija

  公开号：US20050165034A1

  公开（公告）日：2005-07-28

  Novel thrombin inhibitors of the formula I (I)and pharmaceutically acceptable salts thereof are described wherein the substituents in the description have the specific meanings. The compounds are useful as thrombin inhibitors.

  本发明提供了式I（I）及其药学上可接受的盐的新型凝血酶抑制剂，其中描述中的取代基具有特定的含义。这些化合物可用作凝血酶抑制剂。
• Novel thrombin inhibitors incorporating non-basic partially saturated heterobicyclic P1-Arginine mimetics
  作者：Lucija Peterlin-Mašic̆、Gregor Mlinšek、Tomaž Šolmajer、Alenka Trampuš-Bakija、Mojca Stegnar、Danijel Kikelj

  DOI：10.1016/s0960-894x(03)00030-1

  日期：2003.3

  The design, synthesis and biological activity of non-covalent thrombin inhibitors incorporating 4,5,6,7-tetrahydroindazole, 2-methyl-4,5,6,7-tetrahydroindazole, 4,5,6,7-tetrahydroisoindole, 5,6,7,8-tetrahydroquinazoline and 5,6,7,8-tetrahydroquinazolin-2-amine as novel, partially saturated, heterobicyclic P-1-arginine side-chain mimetics is described. The binding mode of the most potent candidate in the series co-crystallized with human alpha-thrombin, which exhibited an in vitro K-i of 140nM and more that 478-fold selectivity against trypsin, is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• THROMBIN INHIBITORS
  申请人：University of Ljubljana

  公开号：EP1451175A1

  公开（公告）日：2004-09-01
• US7524871B2
  申请人：——

  公开号：US7524871B2

  公开（公告）日：2009-04-28
• [EN] THROMBIN INHIBITORS<br/>[FR] INHIBITEURS DE THROMBINE
  申请人：UNIV LJUBLJANA

  公开号：WO2003048155A1

  公开（公告）日：2003-06-12

  Novel thrombin inhibitors of the formula I (I)and pharmaceutically acceptable salts thereof are described wherein the substituents in the description have the specific meanings. The compounds are useful as thrombin inhibitors.