linoleyl chloroformate | 1228447-62-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: linoleyl chloroformate
• 英文别名: [(9Z,12Z)-octadeca-9,12-dienyl] carbonochloridate
• CAS: 1228447-62-8
• 化学式: C₁₉H₃₃ClO₂
• 分子量: 328.923
• InChiKey: NUOTUEUDWPVQBO-HZJYTTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  linoleyl chloroformate 、 5-羟基色胺盐酸盐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以40%的产率得到(9Z,12Z)-octadeca-9,12-dien-1-yl N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]carbamate
  参考文献：
  名称：

  New N-Arachidonoylserotonin Analogues with Potential “Dual” Mechanism of Action against Pain

  摘要：

  N-Arachidonoylserotonin (AA-5-HT, 1a) is an inhibitor of fatty acid amide hydrolase (FAAH) that acts also as an antagonist of transient receptor potential vanilloid-type 1 (TRPV1) channels and is analgesic in rodents. We modified the chemical structure of 1a with the aim of developing "hybrid" FAAH/TRPV1 blockers more potent than the parent compound or obtaining analogues with single activity at either of the two targets to study the mechanism of the analgesic action of 1a. Thirty-eight AA-5-HT analogues, containing a serotonin "head" bound to a variety of lipophilic moieties via amide, urea, or carbamate functionalities, were synthesized. Unlike 1a, most of the new compounds possessed activity at only one of the two considered targets. The amides 1b and 1c of alpha- and gamma-linolenic acid, however, showed "hybrid" activity similar to 1a. The carbarnate 3f (OMDM 106), although unable to antagonize TRPV1 receptors, was the most potent FAAH inhibitor in this study (IC50 = 0.5 mu M). Compounds 3f and 1m (OMDM129), which exhibited activity at only FAAH or TRPV1, respectively, were 10-fold less potent than 1a at preventing formal in-induced hyperalgesia in mice.

  DOI：

  10.1021/jm070678q
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 linoleyl chloroformate
  参考文献：
  名称：

  AMPHIPHILE PRODRUGS

  摘要：

  公开号：

  EP2393472B1

文献信息

• [EN] LIPIDS AND LIPID COMPOSITIONS FOR THE DELIVERY OF ACTIVE AGENTS<br/>[FR] LIPIDES ET COMPOSITIONS LIPIDIQUES DESTINÉS À LA LIBÉRATION D'AGENTS ACTIFS
  申请人：NOVARTIS AG

  公开号：WO2015095346A1

  公开（公告）日：2015-06-25

  This invention provides for a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1-R3, n, p, L1 and L2 are defined herein. The compounds of formula (I) and pharmaceutically acceptable salts thereof are cationic lipids useful in the delivery of biologically active agents to cells and tissues.

  这项发明提供了一种式（I）的化合物或其药学上可接受的盐，其中R1-R3、n、p、L1和L2在此处被定义。式（I）的化合物及其药学上可接受的盐是阳离子脂质，在将生物活性剂传递给细胞和组织方面非常有用。
• [EN] GEMCITABINE AMPHIPHILE PRODRUGS<br/>[FR] PROMÉDICAMENTS AMPHIPHILES À BASE DE GEMCITABINE
  申请人：NANOMED HOLDINGS PTY LTD

  公开号：WO2019204869A1

  公开（公告）日：2019-10-31

  The present invention relates to improved prodrugs, and compositions thereof. In particular, it relates to amphiphilic gemcitabine prodrugs or amphiphilic prodrugs of other biologically active molecules with the capacity to make liquid crystalline nanostructured nanoparticles, and uses thereof to treat animals, including humans.

  本发明涉及改进的前药及其组合物。具体而言，涉及两性的吉西他滨前药或其他生物活性分子的两性前药，具有制备液晶纳米结构纳米颗粒的能力，以及用途包括治疗动物，包括人类。
• Biomimetic Gemcitabine–Lipid Prodrug Nanoparticles for Pancreatic Cancer
  作者：Jerikho C. Bulanadi、Aiqun Xue、Xiaojuan Gong、Penelope A. Bean、Sohel M. Julovi、Liliana Campo、Ross C. Smith、Minoo J. Moghaddam

  DOI：10.1002/cplu.202000253

  日期：2020.6

  crystalline inverse cubic mesophase. This prodrug was combined with phospholipids and cholesterol to create biomimetic Gem‐lipid prodrug nanoparticles (Gem‐LPNP), verified by SSAXS and cryo‐TEM to form liposomes. In vitro testing of the Gem‐LPNP in several pancreatic cancer cell lines showed lower toxicity than Gem. However, in a cell line‐derived pancreatic cancer mouse model Gem‐LPNP displayed greater

  吉西他滨（Gem）是一种用于胰腺癌的关键药物，但受到全身毒性高，生物利用度低和药代动力学不良的限制。为了克服这些局限性，合成了具有油基，亚油基和植烷链的宝石前药两亲物。使用偏振光学显微镜和Synchrotron SAXS（SSAXS）检查了这些两亲物的自组装和溶致中间相行为。发现宝石芬太尼可形成液晶逆立方中间相。将该前药与磷脂和胆固醇结合，制成仿生的宝石脂质前药纳米颗粒（Gem-LPNP），并通过SSAXS和cryo-TEM验证形成脂质体。在几种胰腺癌细胞系中对Gem-LPNP进行的体外测试显示，其毒性低于Gem。然而，在源自细胞系的胰腺癌小鼠模型中，使用临床剂量的一小部分（<6％），Gem-LPNP表现出比Gem更大的肿瘤生长抑制作用，并且没有任何系统毒性。Gem-LPNP的易于生产，提高的疗效和低毒性代表了一种有望用于胰腺癌的新型纳米药物。
• Lipids and lipid compositions for the delivery of active agents
  申请人：Novartis AG

  公开号：US10426737B2

  公开（公告）日：2019-10-01

  This invention provides for a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1-R3, n, p, L1 and L2 are defined herein. The compounds of formula (I) and pharmaceutically acceptable salts thereof are cationic lipids useful in the delivery of biologically active agents to cells and tissues.

  本发明提供了一种式（I）化合物或其药学上可接受的盐，其中 R1-R3、n、p、L1 和 L2 在此定义。式（I）化合物及其药学上可接受的盐是一种阳离子脂质，可用于向细胞和组织递送生物活性剂。
• LIPIDS AND LIPID COMPOSITIONS FOR THE DELIVERY OF ACTIVE AGENTS
  申请人：Novartis AG

  公开号：EP3083579A1

  公开（公告）日：2016-10-26