2-[(tert-butoxycarbonyl)amino]hexadecanol | 142656-58-4

• 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-butoxycarbonyl)amino]hexadecanol
• 英文别名: tert-butyl N-[1-(hydroxymethyl)pentadecyl]carbamate；tert-butyl N-(1-hydroxyhexadecan-2-yl)carbamate
• CAS: 142656-58-4
• 化学式: C₂₁H₄₃NO₃
• 分子量: 357.577
• InChiKey: QJPTYDGYJHVVEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(tert-butoxycarbonyl)amino]hexadecanol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到2-aminohexadecanol
  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
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2-[(tert-butoxycarbonyl)amino]hexadecanol
  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

文献信息

• Resolution of N-Protected Amino Alcohols by Porcine Pancreatic Lipase
  作者：Victoria Magrioti、Irene Fotakopoulou、Nicolaos Athinaios、Panoula Anastasopoulou、Violetta Constantinou-Kokotou、George Kokotos

  DOI：10.2174/157017810790796327

  日期：2010.3.1

  The resolution of 2-amino alcohols protected by urethane-type groups either via porcine pancreatic lipase (PPL) hydrolysis of the corresponding racemic acetates or via PPL catalyzed transesterification of racemic alcohols was studied. In both cases, Boc protecting group led to better chemical yields and enantiopurities than Z and Fmoc protecting groups. Furthermore, a simple and efficient method for

  研究了通过猪胰脂肪酶（PPL）水解相应的外消旋乙酸酯或通过PPL催化的消旋醇酯交换反应，对氨基甲酸酯型基团保护的2-氨基醇的拆分。在这两种情况下，Boc保护基均比Z和Fmoc保护基产生更好的化学收率和对映体纯度。此外，开发了一种简单有效的方法来合成医学上感兴趣的光学纯的（R）-2-氨基十六烷醇。
• Delivery systems
  申请人：——

  公开号：US20040176281A1

  公开（公告）日：2004-09-09

  The invention relates to compounds which are useful in the delivery of a wide variety of therapeutically useful molecules. In particular, the invention relates to compounds which are able to act as carriers for therapeutically useful molecules, and to pharmaceutical agents comprising these carriers. The compounds of the invention comprise a mono- or oligosaccharide, a lipidic moiety, and optionally a linker and/or a spacer. The pharmaceutical agents of the invention are particularly useful for oral administration.

  本发明涉及一种在传递各种治疗有用分子方面有用的化合物。具体而言，本发明涉及能够作为治疗有用分子的载体的化合物，以及包含这些载体的制药剂。本发明的化合物包括单糖或寡糖、脂质基团，以及可选的连接物和/或间隔物。本发明的制药剂对于口服给药特别有用。
• 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 in vitro cytotoxicity of lipophilic platinum(II) complexes
  作者：George Kokotos、Vassiliki Theodorou、Violetta Constantinou-Kokotou、William A. Gibbons、Christos Roussakis

  DOI：10.1016/s0960-894x(98)00256-x

  日期：1998.6

  A number of lipophilic platinum(II) complexes of the general structures cis-[Pt(LA)(2)Cl-2] and [Pt(LD)Cl-2] were synthesised. Long chain amines (LA) and diamines (LD), prepared from lipidic amino acids, were used as ligands. The in vitro cytotoxicity of the complexes was evaluated against four cell lines (P388, NSCLC-N6, E39, M96). cis-Dichloro-bis(2-aminohexadecanol)platinum(II) was the most active against P388, NSCLC-N6 and E39 (IC50: 11 mu g/ml, 25 mu g/ml, 31 mu g/ml), while dichloro(1,3-heptadecanediamine)platinum presented the highest activity against M96 (IC50: 13 mu g/ml). (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.