N-乙酰基-1,6-二氨基己烷盐酸盐 | 61714-20-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-乙酰基-1,6-二氨基己烷盐酸盐
• 英文名称: N-Acetyl-1,6-diaminohexane hydrochloride
• 英文别名: N-Acetylhexane-1,6-diamine Hydrochloride；N-(6-aminohexyl)acetamide hydrochloride；N-(6-aminohexyl)acetamide;hydrochloride
• CAS: 61714-20-3
• 化学式: C₈H₁₈N₂O*ClH
• 分子量: 194.705
• InChiKey: WYCXXBVBKBLSAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-乙酰基-1,6-二氨基己烷盐酸盐 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 54.67h， 生成 N-Acetyl-N'--L-alanyl>hexane-1,6-diamine
  参考文献：
  名称：

  天然存在的蜘蛛毒素的合成类似物

  摘要：

  天然产生的蜘蛛毒素是中枢神经系统谷氨酸受体的有效抑制剂，并具有一般结构（杂）芳基氨基酰胺基（Ⅰ）多胺氨基酰基（Ⅱ）（箭头表示酰胺键的方向）。在本文件中，十蜘蛛毒素的合成类似物13，18，21，28，35，37，39，41，45，和53被报告（方案1-12）。这些化合物的亚基不同，在某些情况下，这些部分的顺序也不同。

  DOI：

  10.1002/hlca.19920750617
• 作为产物：
  描述：

  N-Boc-1,6-己二胺 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 88.0h， 生成 N-乙酰基-1,6-二氨基己烷盐酸盐
  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

• Novel method and compounds
  申请人：SmithKline Beecham p.l.c.

  公开号：US20040010031A1

  公开（公告）日：2004-01-15

  A method for the treatment of conditions associated with a need for inhibition of GSK-3, such as diabetes, dementias such as Alzheimer's disease and manic depression which method comprises the administration of a pharmaceutically effective, non-toxic amount of a compound of formula (I): 1 or a pharmaceutically acceptable derivative thereof, wherein: R is hydrogen, alkyl, aryl, or aralkyl; R 1 is hydrogen, alkyl, aralkyl, hydroxyalkyl or alkoxyalkyl; R 2 is substituted or unsubstituted aryl or substituted or unsubstituted heterocyclyl; R 3 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl or aralkyl wherein the aryl moiety is substituted or unsubstituted; or, R 1 and R 3 together with the nitrogen to which they are attached form a single or fused, optionally substituted, saturated or unsaturated heterocylic ring; to a human or non-human mammal in need thereof, and compounds of formula I.

  一种用于治疗与需要抑制GSK-3相关的疾病的方法，例如糖尿病、阿尔茨海默病和躁郁症，该方法包括向需要的人类或非人类哺乳动物投予化学药效、无毒量的化合物(I)的药物，其中：R为氢、烷基、芳基或芳基烷基；R1为氢、烷基、芳基烷基、羟基烷基或烷氧基烷基；R2为取代或未取代的芳基或取代或未取代的杂环烷基；R3为氢、取代或未取代的烷基、环烷基、烷氧基烷基、取代或未取代的芳基、取代或未取代的杂环烷基或芳基烷基，其中芳基部分为取代或未取代；或者，R1和R3与它们连接的氮一起形成单个或融合的、可选择取代的饱和或不饱和杂环环；以及化合物I的药物可接受衍生物。
• Method and compounds
  申请人：SmithKline Beecham Corporation

  公开号：US06719520B2

  公开（公告）日：2004-04-13

  A method for the treatment of conditions associated with a need for inhibition of GSK-3, such as diabetes, dementias such as Alzheimer's disease and manic depression which method comprises the administration of a pharmaceutically effective, non-toxic amount of a compound of formula (I): or a pharmaceutically acceptable derivative thereof, wherein: R is hydrogen, alkyl, aryl, or aralkyl; R1 is hydrogen, alkyl, aralkyl, hydroxyalkyl or alkoxyalkyl; R2 is substituted or unsubstituted aryl or substituted or unsubstituted heterocyclyl; R3 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl or aralkyl wherein the aryl moiety is substituted or unsubstituted; or, R1 and R3 together with the nitrogen to which they are attached form a single or fused, optionally substituted, saturated or unsaturated heterocylic ring; to a human or non-human mammal in need thereof, and compounds of formula I.

  一种用于治疗与需要抑制GSK-3相关的疾病的方法，例如糖尿病，老年痴呆症，躁郁症，该方法包括给予一种公式（I）化合物或其药学上可接受的衍生物的药学有效、无毒剂量，其中：R是氢、烷基、芳基或芳基烷基；R1是氢、烷基、芳基烷基、羟基烷基或烷氧基烷基；R2是取代或未取代的芳基或取代或未取代的杂环基；R3是氢、取代或未取代的烷基、环烷基、烷氧基烷基、取代或未取代的芳基、取代或未取代的杂环基或芳基烷基，其中芳基基团是取代或未取代的；或者，R1和R3与它们所连接的氮一起形成单个或融合的、可选取代的、饱和或不饱和的杂环环；给予需要该方法的人类或非人哺乳动物，以及公式I化合物。
• Design and synthesis of inhibitors of N8-acetylspermidine deacetylase
  作者：Sasi A. Dredar、James W. Blankenship、Pamela E. Marchant、Victor Manneh、David S. Fries

  DOI：10.1021/jm00125a010

  日期：1989.5

  Analogues of N8-acetylspermidine (1) were synthesized as potential inhibitors of the cytoplasmic enzyme N8-acetylspermidine deacetylase. The compounds were assayed for their ability to inhibit the deacetylation of 1 in a cytosolic fraction from rat liver. The apparent Ki values were determined by Dixon plots. The apparent Km of 1 for this enzyme is 11.0 microM. It was found that compounds which lacked the N1 or the N4 of spermidine were less effective at competing for the enzyme than the substrate. All compounds with acyl substituents larger than acetyl were less potent inhibitors than the corresponding acetylated derivatives. Thus, the enzyme's selectivity as a deacetylase seems to be attributable to steric hindrance which occurs with larger acyl groups. The N8 of the substrate is not essential for its binding to the enzyme. Replacement of N8 with a CH2 group gives the ketone 14, which has an apparent Ki of 0.18 microM, 60-fold lower than the apparent Km of 1. The inhibitory potency of 14 is retained in compounds substituted at the N1 position. The N1,N1-dimethyl and the N1,N1-diethyl analogues (15 and 16) of 14 have apparent Ki values of 0.096 and 0.10 microM, respectively. These agents are the most potent inhibitors of N8-acetylspermidine deacetylase reported, and they are promising tools for use in determining the physiological function of N8-acetylspermidine deacetylation.
• DREDAR, SASI A.;BLANKENSHIP, JAMES W.;MARCHANT, PAMELA E.;MANNEH, VICTOR;+, J. MED. CHEM., 32,(1989) N, C. 984-989
  作者：DREDAR, SASI A.、BLANKENSHIP, JAMES W.、MARCHANT, PAMELA E.、MANNEH, VICTOR、+

  DOI：——

  日期：——
• PYRROLE-2,5-DIONES AS GSK-3 INHIBITORS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1119548A1

  公开（公告）日：2001-08-01