1-cyclohexylaminohexadecan-2-ol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-cyclohexylaminohexadecan-2-ol
• 英文别名: 1-(Cyclohexylamino)hexadecan-2-ol
• 化学式: C₂₂H₄₅NO
• 分子量: 339.605
• InChiKey: HHTCKCAZBGJKJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  十六碳烯 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-cyclohexylaminohexadecan-2-ol
  参考文献：
  名称：

  Long-Chain Aminoalcohol and Diamine Derivatives Induce Apoptosis through a Caspase-3 Dependent Pathway

  摘要：

  A number of long chain diamines and aminoalcohols and several of their alkyl, acyl and carbamoyl derivatives, have been synthesized and evaluated for their apoptotic activities using the Jurkat cell line. Apoptosis was measured by flow cytometry and the best results were found for the aminoalcohols displaying either a free alcohol or an amine with at least, one free hydrogen atom. The apoptotic pathway was mediated by a disruption of the mitochondria transmembrane potential and caspase-3 activation, inducing DNA fragmentation at the phase G(1)/S of the cell cycle. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00476-6

文献信息

• Simple dihydrosphyngosine analogues with potent activity against MDR-Mycobacterium tuberculosis
  作者：Esther del Olmo、Gloria María Molina-Salinas、Ricardo Escarcena、Mario Alves、José L. López-Pérez、Rogelio Hernandez-Pando、Salvador Said-Fernández、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2009.07.147

  日期：2009.10

  Fifteen dihydrosphingosine analogues have been synthesized and tested in vitro against Mycobacterium tuberculosis (MTB). Two ether ( 3 and 4b) and one diamine (8b) derivatives have displayed high mycobactericidal potency, with similar MIC values of 1.25 mu g/mL, against the virulent strain H37Rv, as well as against a clinical isolate resistant to the five first-line anti-TB drugs. The three compounds, tested on other eleven cultured MTB strains with different multi-drug-resistance (MDR) patterns, retained their MIC values for most strains, or even lowered it, as in the case of compound 4b, which, assayed on strain No. 332, also resistant to all first-line anti-TB drugs, attained the MIC value of 0.78 mu g/mL. (C) 2009 Published by Elsevier Ltd.
• Diamine and aminoalcohol derivatives active against Trypanosoma brucei
  作者：Esther del Olmo、Rosario Diaz-González、Ricardo Escarcena、Luis Carvalho、Luis A. Bustos、Miguel Navarro、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2011.10.108

  日期：2012.1

  Twenty compounds selected as representative members of three series of long-chain 1,2-diamines, 2-amino-1-alkanols and 1-amino-2-alkanols structurally related to dihydrosphingosin, were synthesized and tested in vitro for their ability to inhibit the sleeping sickness parasites Trypanosoma brucei rhodesiense and Trypanosoma brucei gambiense. Eight compounds showed EC50 values in the submicromolar range, with selectivity indexes up to 39 related to the respective cytotoxicity values for Vero cells. The parasite phenotype detected after treatment with the most potent compounds showed irreversible cell morphology alterations of the flagellar pocket that lead to inhibition of cell growth and parasite death. (C) 2011 Elsevier Ltd. All rights reserved.
• Long-Chain Aminoalcohol and Diamine Derivatives Induce Apoptosis through a Caspase-3 Dependent Pathway
  作者：Esther del Olmo、Antonio Macho、Mario Alves、José L López、Fadwa el Banoua、Eduardo Muñoz、Arturo San Feliciano

  DOI：10.1016/s0960-894x(02)00476-6

  日期：2002.9

  A number of long chain diamines and aminoalcohols and several of their alkyl, acyl and carbamoyl derivatives, have been synthesized and evaluated for their apoptotic activities using the Jurkat cell line. Apoptosis was measured by flow cytometry and the best results were found for the aminoalcohols displaying either a free alcohol or an amine with at least, one free hydrogen atom. The apoptotic pathway was mediated by a disruption of the mitochondria transmembrane potential and caspase-3 activation, inducing DNA fragmentation at the phase G(1)/S of the cell cycle. (C) 2002 Elsevier Science Ltd. All rights reserved.