diethyl (Z)-2-(octadec-9-en-1-yl)malonate | 187101-32-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: diethyl (Z)-2-(octadec-9-en-1-yl)malonate
• 英文别名: Diethyl 2-oleylmalonate；diethyl 2-[(Z)-octadec-9-enyl]propanedioate
• CAS: 187101-32-2
• 化学式: C₂₅H₄₆O₄
• 分子量: 410.638
• InChiKey: JOJDZGPQHKYBET-YPKPFQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  29
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (Z)-2-(octadec-9-en-1-yl)malonate 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-{[(9Z)-octadec-9-enylamino]carbonyl}-(11Z)-icos-11-enoic acid
  参考文献：
  名称：

  Synthesis and DNA transfection properties of new head group modified malonic acid diamides

  摘要：

  Malonic acid diamides with two long hydrophobic alkyl chains and a basic polar head group as a new class of non-viral gene transferring compounds have shown high transfection efficiency and moderate toxicity. Based on the results obtained with saturated and unsaturated alkyl residues new derivatives with a more complex head group structure have been synthesized. For this purpose, cationic respectively basic groups were introduced by one or two lysine residues bound via tris(aminoethyl)amine spacer to the malonic acid diamide backbone. By studying in vitro gene delivery an increase of transfection efficacy was observed when using lipids with at least one unsaturated alkyl chain. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available transfection agents LipofectAmine (TM) and SuperFect (TM). Phase transitions and phase structures of selected compounds have been analyzed and discussed in terms of transfection abilities. Particle size and zeta potential of liposomes and lipoplexes were also determined. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.02.022
• 作为产物：
  描述：

  油醇 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.75h， 生成 diethyl (Z)-2-(octadec-9-en-1-yl)malonate 、 diethyl 2,2-di((Z)-octadec-9-en-1-yl)malonate
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS
  [FR] COMPOSITIONS ET PROCÉDÉS PERMETTANT D'ADMINISTRER DES AGENTS THÉRAPEUTIQUES

  摘要：

  这项披露提供了改进的基于脂质的组合物，包括脂质纳米粒子组合物，以及它们用于体内传递药剂的方法，包括核酸和蛋白质。这些组合物不受加速血清清除的影响，并且它们在体内具有改进的毒性特性。

  公开号：

  WO2017099823A1

文献信息

• Synthesis of Long‐Chain β‐Lactones and Their Antibacterial Activities against Pathogenic Mycobacteria
  作者：Pierre Santucci、Christina Dedaki、Alexandros Athanasoulis、Laura Gallorini、Anaïs Munoz、Stéphane Canaan、Jean‐François Cavalier、Victoria Magrioti

  DOI：10.1002/cmdc.201800720

  日期：2019.2.5

  the quest for new antibacterial agents, a series of novel long- and medium-chain mono- and disubstituted β-lactones was developed. Their activity against three pathogenic mycobacteria-M. abscessus, M. marinum, and M. tuberculosis-was assessed by the resazurin microtiter assay (REMA). Among the 16 β-lactones synthesized, only 3-hexadecyloxetan-2-one (VM005) exhibited promising activity against M. abscessus

  为了寻求新的抗菌剂，开发了一系列新颖的长链和中链单和双取代β-内酯。它们针对三种致病性分枝杆菌-M的活性。通过刃天青素微量滴定分析（REMA）评估脓肿，海藻分枝杆菌和结核分枝杆菌。在合成的16种β-内酯中，只有3-十六烷基氧杂环丁烷-2-酮（VM005）表现出对脓肿分支杆菌的有希望的活性，而大多数β-内酯表现出了有趣的抗海藻分支杆菌的活性，类似于经典抗生素，异烟肼。关于结核分枝杆菌，发现有六种化合物对这种分枝杆菌有活性，与β-内酯VM008 [反式-（Z）-3-（十六烷基-7-烯-1-基）-4-丙基氧杂环丁烷-2-一]是最好的生长抑制剂。
• [EN] LPA RECEPTOR AGONISTS AND ANTAGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS DE LPA ET ANTAGONISTES
  申请人：RXBIO INC

  公开号：WO2010051053A1

  公开（公告）日：2010-05-06

  Disclosed are compounds according to formula (I) as well as pharmaceutical compositions which include those compounds. Also disclosed are methods of using such compounds, which have activity as agonists or as antagonists of LPA receptors; such methods including treating cancer, producing radioprotection and/or radiomitigation, enhancing cell proliferation, treating a wound, treating apoptosis or preserving or restoring function in a cell, tissue, or organ, culturing cells, preserving organ or tissue function, and treating a dermato logical condition.

  揭示了按照式(I)的化合物，以及包括这些化合物的药物组合物。还揭示了使用这些化合物的方法，这些方法具有作为LPA受体激动剂或拮抗剂的活性；这些方法包括治疗癌症、产生放射保护和/或减轻放射损伤、增强细胞增殖、治疗伤口、治疗凋亡或在细胞、组织或器官中保护或恢复功能、培养细胞、保护器官或组织功能，以及治疗皮肤病理条件。
• US2831865
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel Cationic Lipids Based on Malonic Acid Amides Backbone: Transfection Efficacy and Cell Toxicity Properties
  作者：Martin Heinze、Gerald Brezesinski、Bodo Dobner、Andreas Langner

  DOI：10.1021/bc9004624

  日期：2010.4.21

  Gene delivery using nonviral approaches has been extensively studied as a basic tool for intracellular gene transfer. Despite intensive research activity, the aim of creating a vector which meets all necessary demands has still not been reached. One possibility to solve the nonviral vector associated problem of low transfection efficacy is the development of new cationic amphiphiles. Therefore, the non-glycerol-based cationic lipids 1-9 have been synthesized and tested for in vitro gene delivery experiments. The backbone structure of the lipids consists of a malonic acid diamide with two long hydrophobic chains. The degree of saturation of the hydrophobic chains and the structure of the polar cationic headgroup were varied. The preparation follows an easy process and facilitates the trouble-free insertion of different alkyl chains. By studying in vitro gene delivery an increase of transfection efficacy was observed when using at least one unsaturated alkyl chain in the hydrophobic part and lysine or bis(2-aminoethyl)aminoethylamid as hydrophilic headgroup. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available LipolectAmine and Super Feet.