6-amino-N-phenyl-hexanamide hydrochloric acid salt | 59472-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-amino-N-phenyl-hexanamide hydrochloric acid salt
• 英文别名: 6-aminohexaneanilide hydrochloride；H-ε-Aca-NH-Phenyl*HCl；6-amino-hexanoic acid anilide; hydrochloride；6-Amino-hexansaeure-anilid; Hydrochlorid；6-aminocaproanilide hydrochloride；6-amino-N-phenylhexanamidehydrochloride；6-amino-N-phenylhexanamide;hydrochloride
• CAS: 59472-16-1
• 化学式: C₁₂H₁₈N₂O*ClH
• 分子量: 242.749
• InChiKey: JLXJEAGXCZRIDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  6-amino-N-phenyl-hexanamide hydrochloric acid salt 在 劳森试剂 、 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.0h， 生成 N-phenyl-6-[(2-sulfanylethanethioyl)amino]hexanamide
  参考文献：
  名称：

  Carbonyl- and sulfur-containing analogs of suberoylanilide hydroxamic acid: Potent inhibition of histone deacetylases

  摘要：

  Suberoylanilide hydroxamic acid (SAHA), an inhibitor of histone deacetylase, is used in clinical trials for a variety of advanced cancers. Twelve new analogs of SAHA were synthesized and tested as in vitro inhibitors of isolated histone deacetylases (HDACS) and in vivo inhibitors of interferon regulated transcriptional responses (a marker for HDAC activity). The analogs containing an alpha-mercaptoketone or an alpha-thioacetoxyketone were more potent than SAHA in both assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.047
• 作为产物：
  描述：

  6-phthalimido-hexanoic acid anilide 在 一水合肼 作用下， 生成 6-amino-N-phenyl-hexanamide hydrochloric acid salt
  参考文献：
  名称：

  van der Want; Staverman, Recueil des Travaux Chimiques des Pays-Bas, 1952, vol. 71, p. 379,383

  摘要：

  DOI：

文献信息

• The Effect of Various Zinc Binding Groups on Inhibition of Histone Deacetylases 1-11
  作者：Andreas S. Madsen、Helle M. E. Kristensen、Gyrithe Lanz、Christian A. Olsen

  DOI：10.1002/cmdc.201300433

  日期：2014.3

  putative new zinc binding domains. By evaluating the compound collection against all 11 recombinant human HDACs, we found that the trifluoromethyl ketone functionality provides potent inhibition of all four subclasses of the Zn2+‐dependent HDACs. Potent inhibition was observed with two different scaffolds, demonstrating the efficiency of the trifluoromethyl ketone moiety as a zinc binding motif. Interestingly

  组蛋白脱乙酰基酶（HDAC）具有裂解多种蛋白质中ε - N-乙酰化赖氨酸残基的乙酰基的能力。鉴于人类细胞包含成千上万个不同的乙酰化赖氨酸残基，HDACS可以调节多种过程，包括某些与癌症和神经退行性疾病等疾病有关的过程。在这里，我们报告了一系列化合物的合成和体外生化分析，包括已知的抑制剂以及新颖的化学型，这些化合物结合了新的锌结合域。通过评估针对所有11种重组人HDAC的化合物集合，我们发现三氟甲基酮官能团可有效抑制Zn 2+的所有四个亚类依赖的HDAC。用两种不同的支架观察到有效的抑制作用，证明了三氟甲基酮部分作为锌结合基序的效率。有趣的是，我们还将硅烷二醇确定为锌结合基团，对于将来开发非I-异羟肟酸酯I类和IIb B类HDAC抑制剂具有潜力。
• THIAZOLINE DERIVATIVE
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0765875A1

  公开（公告）日：1997-04-02

  Object: To provide compounds useful as inhibitors of blood platelet aggregation for intravenous administration. Constitution: A thiazoline derivative represented by the formula: [wherein R1 is a hydroxyl group, an alkoxy group, a cycloalkoxy group or a group represented by the formula: R4NH- (wherein R4 is a cycloalkyl group), R2 is an alkyl group, a cycloalkyl group or a phenylalkyl group, R3 is a hydrogen atom or an alkyl group, and n is an integer of 2 to 9] or a salt thereof.

  目的提供可作为血小板聚集抑制剂用于静脉注射的化合物。 组成：一种噻唑啉衍生物，由式： [其中 R1 是羟基、烷氧基、环烷氧基或由式表示的基团：R4NH-（其中 R4 为环烷基），R2 为烷基、环烷基或苯烷基，R3 为氢原子或烷基，n 为 2 至 9 的整数]或其盐。
• Ishibashi, Norio; Kouge, Katsushige; Shinoda,Ichizo, Agricultural and Biological Chemistry, 1988, vol. 52, # 3, p. 819 - 828
  作者：Ishibashi, Norio、Kouge, Katsushige、Shinoda,Ichizo、Kanehisa, Hidenori、Okai, Hideo

  DOI：——

  日期：——
• Phosphorus-Based SAHA Analogues as Histone Deacetylase Inhibitors
  作者：Galina V. Kapustin、György Fejér、Jennifer L. Gronlund、Dewey G. McCafferty、Edward Seto、Felicia A. Etzkorn

  DOI：10.1021/ol035056n

  日期：2003.8.1

  graphicThree analogues of suberoyl anilide hydroxamic acid (SAHA) with phosphorus metal-chelating functionalities were synthesized as inhibitors of histone deacetylases (HDACs). The compounds showed weak activity for HeLa nuclear extracts (IC50 = 0.57-6.1 mM), HDAC8 (IC50 = 0.28-0.41 mM), and histone-deacetylase-like protein (HDLP, IC50 = 0.33-1.9 mM), suggesting that the transition state of HDAC is not analogous to zinc proteases. Anti proliferative activity against A2780 cancer cells (IC50 = 0.11-0.12 mM), comparable to SAHA (0.15 mM), was observed.
• US5672712A
  申请人：——

  公开号：US5672712A

  公开（公告）日：1997-09-30