Ethyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]hexadecylamino]acetate | 267242-62-6

• 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: Ethyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]hexadecylamino]acetate
• CAS: 267242-62-6
• 化学式: C₂₅H₅₀N₂O₄
• 分子量: 442.683
• InChiKey: KSYTXIPCXZXMFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  31
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]hexadecylamino]acetate 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 Ethyl 2-(2-aminohexadecylamino)acetate
  参考文献：
  名称：

  Leishmanicidal activity of some aliphatic diamines and amino-Alcohols

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(01)00837-x
• 作为产物：
  描述：

  2-[(tert-butoxycarbonyl)amino]hexadecanol 在 palladium on activated charcoal sodium tetrahydroborate 、 sodium azide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]hexadecylamino]acetate
  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

• 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。
• 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.
• 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.
• 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