6-amino-hexanoic acid amide; hydrochloride | 5439-29-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-amino-hexanoic acid amide; hydrochloride
• 英文别名: 6-Amino-hexansaeure-amid; Hydrochlorid；5-aminopentylcarboxamide hydrochloride；6-Aminohexanamide hydrochloride；6-aminohexanamide;hydrochloride
• CAS: 5439-29-2
• 化学式: C₆H₁₄N₂O*ClH
• 分子量: 166.651
• InChiKey: UOGKXMNHWNLXTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(7,8-dimethoxy-1-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-5-yl)benzoic acid 、 6-amino-hexanoic acid amide; hydrochloride 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到N-(6-amino-6-oxohexyl)-3-(7,8-dimethoxy-1-methyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-5-yl)benzamide
  参考文献：
  名称：

  Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses

  摘要：

  本发明涉及使用PDE2抑制剂治疗中枢和周围神经系统疾病的方法，以及通过向动物投予所述抑制剂进行治疗的方法。更具体地说，本发明涉及新的苯二氮卓酮衍生物及其在治疗学中的用途，尤其是用于治疗涉及环核苷酸磷酸二酯酶2活性的病理学。本发明还涉及制备相同的方法和新颖的合成中间体。

  公开号：

  US20060128695A1
• 作为产物：
  描述：

  ε-<(tert-Butoxycarbonyl)amino>capronamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 6-amino-hexanoic acid amide; hydrochloride
  参考文献：
  名称：

  The structure-activity profile of mercaptobenzamides’ anti-HIV activity suggests that thermodynamics of metabolism is more important than binding affinity to the target

  摘要：

  Mercaptobenzamide thioesters and thioethers are chemically simple HIV-1 maturation inhibitors with a unique mechanism of action, low toxicity, and a high barrier to viral resistance. A structure-activity relationship (SAR) profile based on 39 mercaptobenzamide prodrug analogs exposed divergent activity/toxicity roles for the internal and terminal amides. To probe the relationship between antiviral activity and toxicity, we generated an improved computational model for the binding of mercaptobenzamide thioesters (SAMTs) to the HIV-1 NCp7 C-terminal zinc finger, revealing the presence of a second low-energy binding orientation, hitherto undisclosed. Finally, using NMR-derived thiol -thioester exchange equilibrium constants, we propose that thermodynamics plays a role in determining the antiviral activity observed in the SAR profile. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.06.020

文献信息

• Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses
  申请人：Bourguignon Jean-Jacques

  公开号：US20060128695A1

  公开（公告）日：2006-06-15

  The invention concerns the use of PDE2 inhibitors for treating disorders of the central and peripheral nervous system, a method for therapeutic treatment by administering to an animal said inhibitors. More specifically, the invention concerns novel benzodiazepinone derivatives and their uses in therapeutics more particularly for treating pathologies involving activity of a cyclic nucleotide phosphodiesterase type 2. The invention also concerns methods for preparing same and novel synthesis intermediates.

  本发明涉及使用PDE2抑制剂治疗中枢和周围神经系统疾病的方法，以及通过向动物投予所述抑制剂进行治疗的方法。更具体地说，本发明涉及新的苯二氮卓酮衍生物及其在治疗学中的用途，尤其是用于治疗涉及环核苷酸磷酸二酯酶2活性的病理学。本发明还涉及制备相同的方法和新颖的合成中间体。
• The structure-activity profile of mercaptobenzamides’ anti-HIV activity suggests that thermodynamics of metabolism is more important than binding affinity to the target
  作者：Herman Nikolayevskiy、Marco Robello、Michael T. Scerba、Evan H. Pasternak、Mrinmoy Saha、Tracy L. Hartman、Caitlin A. Buchholz、Robert W. Buckheit、Stewart R. Durell、Daniel H. Appella

  DOI：10.1016/j.ejmech.2019.06.020

  日期：2019.9

  Mercaptobenzamide thioesters and thioethers are chemically simple HIV-1 maturation inhibitors with a unique mechanism of action, low toxicity, and a high barrier to viral resistance. A structure-activity relationship (SAR) profile based on 39 mercaptobenzamide prodrug analogs exposed divergent activity/toxicity roles for the internal and terminal amides. To probe the relationship between antiviral activity and toxicity, we generated an improved computational model for the binding of mercaptobenzamide thioesters (SAMTs) to the HIV-1 NCp7 C-terminal zinc finger, revealing the presence of a second low-energy binding orientation, hitherto undisclosed. Finally, using NMR-derived thiol -thioester exchange equilibrium constants, we propose that thermodynamics plays a role in determining the antiviral activity observed in the SAR profile. (C) 2019 Published by Elsevier Masson SAS.