(+/-)-6-(aminomethyl)-5,6,7,8-tetrahydro-2-quinazolinamine | 299180-16-8

• 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-tetrahydro-2-quinazolinamine
• 英文别名: 6-(amino-methyl)-5,6,7,8-tetrahydro-2-quinazolinamine；6-(aminomethyl)-5,6,7,8-tetrahydro-2-quinazolinamine；6-(aminomethyl)-5,6,7,8-tetrahydroquinazolin-2-amine
• CAS: 299180-16-8
• 化学式: C₉H₁₄N₄
• 分子量: 178.237
• InChiKey: HAEGEBQQKQLPRP-UHFFFAOYSA-N

物化性质

• 沸点：
  412.7±37.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 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：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-6-(aminomethyl)-5,6,7,8-tetrahydro-2-quinazolinamine 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 溶剂黄146 、 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 0.5h， 生成 (S)-1-((R)-2-Amino-3,3-diphenyl-propionyl)-pyrrolidine-2-carboxylic acid (2-amino-5,6,7,8-tetrahydro-quinazolin-6-ylmethyl)-amide
  参考文献：
  名称：

  Novel thrombin inhibitors incorporating non-basic partially saturated heterobicyclic P1-Arginine mimetics

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(03)00030-1
• 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 43.0h， 生成 (+/-)-6-(aminomethyl)-5,6,7,8-tetrahydro-2-quinazolinamine
  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：——

  公开号：US20030191139A1

  公开（公告）日：2003-10-09

  The invention relates to compounds of formula I D—CO—B—A-Het and pharmaceutically acceptable salts thereof where substituents in description have the specified meanings. The compounds are used as thrombin inhibitors.

  该发明涉及公式I的化合物D—CO—B—A-Het及其药用可接受的盐，其中描述中的取代基具有指定的含义。这些化合物被用作凝血酶抑制剂。
• A general synthesis of novel conformationally restricted arginine side-chain mimetics
  作者：Lucija P Mašič、Danijel Kikelj

  DOI：10.1016/s0040-4039(00)00869-8

  日期：2000.7

  6-(Aminomethyl)-5,6,7,8-tetrahydro-2-quinazolinamine and 4,5,6,7-tetrahydro-2H-indazol-5-ylmethanamine were synthesized as novel conformationally restricted arginine side-chain mimetics, designed for incorporation into trypsin-like serine protease inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Selective 3-Amino-2-pyridinone acetamide thrombin inhibitors incorporating weakly basic partially saturated heterobicyclic P1-Arginine mimetics
  作者：Lucija Peterlin-Mašič、Andreja Kranjc、Petra Marinko、Gregor Mlinšek、Tomaž Šolmajer、Mojca Stegnar、Danijel Kikelj

  DOI：10.1016/s0960-894x(03)00717-0

  日期：2003.10

  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.
• THROMBIN INHIBITORS
  申请人：Lek Pharmaceutical and Chemical Co. D.D.

  公开号：EP1287018A2

  公开（公告）日：2003-03-05
• US7112590B2
  申请人：——

  公开号：US7112590B2

  公开（公告）日：2006-09-26