2-(ethylamino)hexadecanol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(ethylamino)hexadecanol
• 英文别名: 2-(Ethylamino)hexadecan-1-ol
• 化学式: C₁₈H₃₉NO
• 分子量: 285.514
• InChiKey: NBFXPOZVZVLLKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• 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：

  2-溴十六烷酸 在 lithium aluminium tetrahydride 作用下， 生成 2-(ethylamino)hexadecanol
  参考文献：
  名称：

  Synthesis and evaluation of some lipidic aminoalcohols and diamines as immunomodulators

  摘要：

  Lymphoproliferation inhibition and cytotoxicity of a number of lipidic aminoacids, aminoalcohols and diamines were evaluated as a preliminary screening to select potential immunomodulators. The four most potent/less toxic compounds were submitted to delayed hypersensibility (DTH) assays to define the best to be evaluated further Graft-vs-Host, NO production and other immunoevaluation (CD4(+), CD45, CD8, CD11b, I-Ek, and NK cells) assays, to establish their immunomodulation potential for being further considered as auxiliary agents for vaccination against some parasitic infections. Compounds 5d, 6d, 6f, 7a, and 9a, fairly inhibited the lymphoproliferation (71.6-79.5%, at 3.2-2.4 nM), while the antinoalcohol derivative 6f and the diamine 7a gave the most promising results in the DTH assays. Diamine derivative 8b induced nitrite production on normal macrophages, whereas compounds 6f and 7a induced nitrite production on LPS pre-stimulated macrophages. These two last compounds have been selected to follow in vivo vaccination assays. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.113

文献信息

• Trypanocidal Activity of Long Chain Diamines and Aminoalcohols
  作者：Ana Legarda-Ceballos、Esther del Olmo、Julio López-Abán、Ricardo Escarcena、Luis Bustos、Cristina Fonseca-Berzal、Alicia Gómez-Barrio、Juan Dib、Arturo Feliciano、Antonio Muro

  DOI：10.3390/molecules200611554

  日期：——

  Thirteen aminoalcohols and eight diamines were obtained and tested against Trypanosoma cruzi epimastigotes strains MG, JEM and CL-B5 clone. Some of them were equal or more potent (1.0–6.6 times) than the reference compound nifurtimox. From them, three aminoalcohols and two diamines were selected for amastigotes assays. Compound 5 was as potent as the reference drug nifurtimox against amastigotes of the CL-B5 strain (IC50 = 0.6 µM), with a selectivity index of 54.

  获得了十三种氨基醇和八种二胺，并对其进行抗克鲁兹锥虫的上位体株MG、JEM和CL-B5克隆进行了测试。其中一些的活性与参考化合物尼夫替莫司相等或更强（1.0–6.6倍）。从中选择了三种氨基醇和两种二胺进行阿米巴虫检测试验。化合物5在对CL-B5株的阿米巴虫的活性与参考药物尼夫替莫司相当（IC50 = 0.6 µM），选择性指数为54。
• Synthesis and enzyme inhibitory activities of a series of lipidic diamine and aminoalcohol derivatives on cytosolic and secretory phospholipases A 2
  作者：Rut Lucas、Amalia Úbeda、Miguel Payá、Mario Alves、Esther del Olmo、José L. López、Arturo San Feliciano

  DOI：10.1016/s0960-894x(99)00680-0

  日期：2000.2

  We have synthesised some lipidic diamines and aminoalcohols and examined their behaviour as inhibitors of secretory and cytosolic PLA2. Some structure-activity relationships considerations have been deduced. Compound 14 was a potent and selective inhibitor of cPLA2 and compound 4 showed a dual inhibitory profile against both types of PLA2 while no cytotoxicity at 10 microM on human neutrophils or on

  我们已经合成了一些脂质二胺和氨基醇，并检查了它们作为分泌型和胞质PLA2抑制剂的行为。推论了一些构效关系。化合物14是cPLA2的有效和选择性抑制剂，化合物4对两种类型的PLA2均表现出双重抑制作用，而在10μM时对人嗜中性粒细胞或鼠巨噬细胞系均未观察到细胞毒性。
• Leishmanicidal activity of some aliphatic diamines and amino-Alcohols
  作者：Esther del Olmo、Mario Alves、José L López、Alba Inchaustti、Gloria Yaluff、Antonieta Rojas de Arias、Arturo San Feliciano

  DOI：10.1016/s0960-894x(01)00837-x

  日期：2002.2

  A number of aliphatic diamines and amino-alcohols and several of their alkyl, acyl and carbamoyl derivatives, have been synthesised and evaluated in vitro on cultures of Leishmania spp. In general, diamine derivatives resulted to be more potent than their amino-alcohol or amino-ether analogues. Two diamine derivatives (8b and 9d) and one amino-alcohol (6a) showed a fair inhibition of parasite growth, at concentrations below 10 mug/mL, with potencies close to that of the reference drug, amphotericin B. Some SAR considerations have been deduced. (C) 2002 Elsevier Science 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.
• In vitro bioevaluation and docking study of dihydrosphingosine and ethambutol analogues against sensitive and multi-drug resistant Mycobacterium tuberculosis
  作者：Leonardo Aquino Linhares、Aline dos Santos Peixoto、Luanna de Angelis Correia de Sousa、João Paulo Lucena Laet、Aline Caroline da Silva Santos、Valeria Rêgo Alves Pereira、Maria Madileuza Carneiro Neves、Luiz Felipe Gomes Rebello Ferreira、Marcelo Zaldini Hernandes、Jennifer de la Vega、Antônio Pereira-Neves、Arturo San Feliciano、Esther Del Olmo、Haiana Charifker Schindler、Lílian Maria Lapa Montenegro

  DOI：10.1016/j.ejmech.2023.115579

  日期：2023.10