5-(n-decyl)salicylic acid | 28488-51-9

• 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: 5-(n-decyl)salicylic acid
• 英文别名: 5-Decyl-2-hydroxybenzoic acid
• CAS: 28488-51-9
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: AOFLEENSAJGSSY-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C(Solv: ligroine (8032-32-4))
• 沸点：
  420.9±38.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(n-decyl)salicylic acid 在 盐酸 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.0h， 生成 5-Decyl-2-(1,4,7,10,13-pentaoxacyclopentadec-2-ylmethoxy)benzoic acid
  参考文献：
  名称：

  Novel Liphophilic crown car☐ylic acids

  摘要：

  DOI：

  10.1016/s0040-4039(00)88059-4
• 作为产物：
  描述：

  水杨酸甲酯 在 盐酸 、 sodium hydroxide 、 三氯化铝 、 mercury dichloride 、 锌 作用下， 以 二硫化碳 为溶剂， 反应 44.0h， 生成 5-(n-decyl)salicylic acid
  参考文献：
  名称：

  Potential salicylamide antiplaque agents: in vitro antibacterial activity against Actinomyces viscosus

  摘要：

  A series of 55 salicylamides, including 3,5-dibromo-, 5-n-alkyl-, and 5-n-acylsalicyloyl derivatives of various anilines, heterocyclic amines, benzylamines, and alkylamines, was synthesized and evaluated for in vitro antibacterial activity against Actinomyces viscosus, an adherent oral microorganism implicated in periodontal disease. The in vitro minimum inhibitory concentrations of 15 4'-bromosalicylanilides were found to correlate (r = 0.92) with estimated log D values. Several nonhalogenated salicylanilides, such as 5-n-hexyl- (40) and 5-n-decanoyl-4'-nitrosalicylanilide (47), were found to exhibit higher levels of in vitro antibacterial activity against a number of Actinomycetes than did tribromsalan (1) or fluorophene (2).

  DOI：

  10.1021/jm00142a023

文献信息

• Enzyme kinetics and inhibition of histone acetyltransferase KAT8
  作者：Hannah Wapenaar、Petra E. van der Wouden、Matthew R. Groves、Dante Rotili、Antonello Mai、Frank J. Dekker

  DOI：10.1016/j.ejmech.2015.10.016

  日期：2015.11

  Lysine acetyltransferase 8 (KAT8) is a histone acetyltransferase (HAT) responsible for acetylating lysine 16 on histone H4 (H4K16) and plays a role in cell cycle progression as well as acetylation of the tumor suppressor protein p53. Further studies on its biological function and drug discovery initiatives will benefit from the development of small molecule inhibitors for this enzyme. As a first step

  赖氨酸乙酰转移酶 8 (KAT8) 是一种组蛋白乙酰转移酶 (HAT)，负责乙酰化组蛋白 H4 (H4K16) 上的赖氨酸 16，并在细胞周期进程以及肿瘤抑制蛋白 p53 的乙酰化中发挥作用。对其生物学功能和药物发现计划的进一步研究将受益于这种酶的小分子抑制剂的开发。作为实现这一目标的第一步，我们研究了这种双底物酶的酶动力学。动力学实验表明了一种乒乓机制，其中酶首先结合 Ac-CoA，然后结合组蛋白底物。这种机制得到了使用等温滴定量热法 (ITC) 对两种底物的亲和力测量的支持。使用这些信息，已经研究了 KAT8 对非选择性 HAT 抑制剂漆树酸周围集中化合物集合的抑制作用。用漆树酸进行了动力学研究，在此基础上提出了 KAT8 的催化活性和漆树酸 (AA) 的抑制作用的模型。这使得能够计算抑制常数 Ki使用 Cheng-Prusoff 方程改编的漆树酸衍生物。本研究中描述的结果深入了解了 KAT8
• Czech, Bronislaw P.; Czech, Anna; Son, Byungki, Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 465 - 471
  作者：Czech, Bronislaw P.、Czech, Anna、Son, Byungki、Lee, Han Koo、Bartsch, Richard A.

  DOI：——

  日期：——
• 6-alkylsalicylates are selective Tip60 inhibitors and target the acetyl-CoA binding site
  作者：Massimo Ghizzoni、Jiang Wu、Tielong Gao、Hidde J. Haisma、Frank J. Dekker、Y. George Zheng

  DOI：10.1016/j.ejmech.2011.11.001

  日期：2012.1

  Histone acetyltransferases are important enzymes that regulate various cellular functions, such as epigenetic control of DNA transcription. Development of HAT inhibitors with high selectivity and potency will provide powerful mechanistic tools for the elucidation of the biological functions of HATs and may also have pharmacological value for potential new therapies. In this work, analogs of the known HAT inhibitor anacardic acid were synthesized and evaluated for inhibition of HAT activity. Biochemical assays revealed novel anacardic acid analogs that inhibited the human recombinant enzyme Tip60 selectively compared to PCAF and p300. Enzyme kinetics studies demonstrated that inhibition of Tip60 by one such novel anacardic acid derive, 20, was essentially competitive with Ac-CoA and non-competitive with the histone substrate. In addition, these HAT inhibitors effectively inhibited acetyltransferase activity of nuclear extracts on the histone H3 and H4 at micromolar concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.
• CZECH, B.;SON, BYUNGKI;BARTSCH, R. A., TETRAHEDRON LETT., 1983, 24, N 29, 2923-2926
  作者：CZECH, B.、SON, BYUNGKI、BARTSCH, R. A.

  DOI：——

  日期：——
• Potential salicylamide antiplaque agents: in vitro antibacterial activity against Actinomyces viscosus
  作者：Robert A. Coburn、Armando J. Batista、Richard T. Evans、Robert J. Genco

  DOI：10.1021/jm00142a023

  日期：1981.10

  A series of 55 salicylamides, including 3,5-dibromo-, 5-n-alkyl-, and 5-n-acylsalicyloyl derivatives of various anilines, heterocyclic amines, benzylamines, and alkylamines, was synthesized and evaluated for in vitro antibacterial activity against Actinomyces viscosus, an adherent oral microorganism implicated in periodontal disease. The in vitro minimum inhibitory concentrations of 15 4'-bromosalicylanilides were found to correlate (r = 0.92) with estimated log D values. Several nonhalogenated salicylanilides, such as 5-n-hexyl- (40) and 5-n-decanoyl-4'-nitrosalicylanilide (47), were found to exhibit higher levels of in vitro antibacterial activity against a number of Actinomycetes than did tribromsalan (1) or fluorophene (2).