2-(tert-butoxycarbonylamino)hexadecanamine | 142656-69-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(tert-butoxycarbonylamino)hexadecanamine
• 英文别名: tert-butyl N-[1-(aminomethyl)pentadecyl]carbamate；tert-butyl N-(1-aminohexadecan-2-yl)carbamate
• CAS: 142656-69-7
• 化学式: C₂₁H₄₄N₂O₂
• 分子量: 356.593
• InChiKey: WFHLXOBAUMFTBL-UHFFFAOYSA-N

物化性质

• 熔点：
  56 °C
• 沸点：
  460.5±28.0 °C(Predicted)
• 密度：
  0.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butoxycarbonylamino)hexadecanamine 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N1,N1-diethylhexadecane-1,2-diamine
  参考文献：
  名称：

  一系列脂质二胺和氨基醇衍生物对胞质和分泌型磷脂酶A2的合成和酶抑制活性。

  摘要：

  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。

  DOI：

  10.1016/s0960-894x(99)00680-0
• 作为产物：
  描述：

  2-[(tert-butoxycarbonyl)amino]hexadecanol 在 sodium tetrahydroborate 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 2-(tert-butoxycarbonylamino)hexadecanamine
  参考文献：
  名称：

  Trypanocidal Activity of Long Chain Diamines and Aminoalcohols

  摘要：

  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。

  DOI：

  10.3390/molecules200611554

文献信息

• Kokotos, George; Constantinou-Kokotou, Violetta; Fernandez, Esther del Olmo, Liebigs Annalen der Chemie, 1992, # 9, p. 961 - 964
  作者：Kokotos, George、Constantinou-Kokotou, Violetta、Fernandez, Esther del Olmo、Toth, Istvan、Gibbons, William A.

  DOI：——

  日期：——
• 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.
• 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.
• 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.