2-[(2-Methylpropan-2-yl)oxycarbonylamino]hexadecyl methanesulfonate | 142656-65-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-[(2-Methylpropan-2-yl)oxycarbonylamino]hexadecyl methanesulfonate
• CAS: 142656-65-3
• 化学式: C₂₂H₄₅NO₅S
• 分子量: 435.669
• InChiKey: RWGQAZKPMWOTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-Methylpropan-2-yl)oxycarbonylamino]hexadecyl methanesulfonate 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 sodium azide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 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)hexadecanoic acid 在 N-甲基吗啉 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 2-[(2-Methylpropan-2-yl)oxycarbonylamino]hexadecyl methanesulfonate
  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

• 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。
• 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.