(+/-)-N-({3-[(dimethylamino)methylidene]-4-oxocyclohexyl}methyl)acetamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 英文名称: (+/-)-N-({3-[(dimethylamino)methylidene]-4-oxocyclohexyl}methyl)acetamide
• 英文别名: N-[[(3Z)-3-(dimethylaminomethylidene)-4-oxocyclohexyl]methyl]acetamide
• 化学式: C₁₂H₂₀N₂O₂
• 分子量: 224.303
• InChiKey: FZKZFMRBTYHZTM-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-N-({3-[(dimethylamino)methylidene]-4-oxocyclohexyl}methyl)acetamide 在 sodium hydroxide 、 水 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 19.0h， 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
• 作为产物：
  描述：

  4-氰基环己酮缩乙二醇 在 lithium aluminium tetrahydride 、 甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 35.0h， 生成 (+/-)-N-({3-[(dimethylamino)methylidene]-4-oxocyclohexyl}methyl)acetamide
  参考文献：
  名称：

  A general synthesis of novel conformationally restricted arginine side-chain mimetics

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)00869-8

文献信息

• 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.
• 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.
• A general synthetic approach to novel conformationally restricted arginine side chain mimetics
  作者：Lucija Peterlin-Mašič、Andreja Jurca、Petra Marinko、Anita Jančar、Danijel Kikelj

  DOI：10.1016/s0040-4020(01)01243-1

  日期：2002.2

  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.