2-(hex-1-ylamino)hexadecan-1-ol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(hex-1-ylamino)hexadecan-1-ol
• 英文别名: 2-(Hexylamino)hexadecan-1-ol
• 化学式: C₂₂H₄₇NO
• 分子量: 341.621
• InChiKey: YMPVPXCPOKBOON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  24
• 可旋转键数：
  20
• 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-(hex-1-ylamino)hexadecan-1-ol
  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

• Mechanisms of Action of Substituted β-Amino Alkanols on Leishmania donovani
  作者：María Ángeles Abengózar、Luis A. Bustos、Raquel García-Hernández、Pilar Fernández de Palencia、Ricardo Escarcena、Santiago Castanys、Esther del Olmo、Francisco Gamarro、Arturo San Feliciano、Luis Rivas

  DOI：10.1128/aac.04003-14

  日期：2015.2

  N-substituted 2-aminoalkan-1-ol scaffold has been shown to be a versatile scaffold for antiparasitic activity. Knowledge about its mechanism of action is still rather limited. In this work, we endeavored to define the leishmanicidal profile of such β-amino alkanol derivatives using a set of 15 N-mono- and disubstituted surrogates, tested on Leishmania donovani promastigotes and intracellular amastigotes

  利什曼病是原生动物疾病，对人类健康的重要性仅次于疟疾。然而，由于耐药性和毒性，化学疗法的选择越来越受到限制。在这种情况下，迫切需要寻找新的化学化合物。N-取代的2-氨基烷-1-醇支架已被证明是具有抗寄生虫活性的通用支架。关于其作用机理的知识仍然相当有限。在这项工作中，我们努力使用一组15种N-单取代和双取代的替代物来定义此类β-氨基链烷醇衍生物的杀菌作用，并在Leishmania donovani前鞭毛体和胞内变形虫上进行了测试。最好的化合物（化合物5）2-乙基氨基十二烷-1-醇的50％有效浓度（EC50）为0。对感染的THP-1细胞具有3μM的选择性和72的选择性指数，并被选择用于进一步阐明其杀菌作用。在没有重要的染料细胞内进入的情况下，它诱导了前鞭毛体中细胞内ATP含量的快速消耗，从而排除了质膜通透性的起源。共聚焦和透射电子显微镜分析表明，化合物5引起严重的线粒体肿胀和囊泡形成。使用氧
• 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
• Synthesis and evaluation of some lipidic aminoalcohols and diamines as immunomodulators
  作者：Esther del Olmo、Alvaro Plaza、Antonio Muro、Antonio R. Martínez-Fernández、Juan J. Nogal-Ruiz、José L. López-Pérez、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2006.08.113

  日期：2006.12

  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.