(9Z)-nonadec-9-enoic acid | 29204-01-1

• 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: (9Z)-nonadec-9-enoic acid
• 英文别名: oleic acid；palmitoleic acid；cis-9-Nonadecensaeure；cis-9-Nonadecenoic acid；(Z)-nonadec-9-enoic acid
• CAS: 29204-01-1
• 化学式: C₁₉H₃₆O₂
• 分子量: 296.494
• InChiKey: YOKHLRHWEXTWJR-KHPPLWFESA-N

物化性质

• 熔点：
  21.0-22.2 °C
• 沸点：
  388.1±11.0 °C(Predicted)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (9Z)-nonadec-9-enoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (2R)-2-hydroxy-3-(phosphonooxy)propyl (9Z)-nonadec-9-enoate
  参考文献：
  名称：

  A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA₁), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

  摘要：

  Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA(1)) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA(1) agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA(1) receptor agonist described so far (E-max = 118%, EC50 = 0.24 mu M, KD = 19.6 nM; inactive at autotaxin and LPA(2-6) receptors). This compound induces characteristic LPA(1)-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

  DOI：

  10.1021/acs.jmedchem.9b01287
• 作为产物：
  描述：

  1,7-二碘庚烷 在 镍 氢气 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 (9Z)-nonadec-9-enoic acid
  参考文献：
  名称：

  Grimmer,G.; Kracht,J., Chemische Berichte, 1963, vol. 96, p. 3370 - 3373

  摘要：

  DOI：

文献信息

• Facile and selective deprotection of PMB ethers and esters using oxalyl chloride
  作者：Andivelu Ilangovan、Karnambaram Anandhan、Mahabir Prasad Kaushik

  DOI：10.1016/j.tetlet.2015.01.061

  日期：2015.2

  Oxalyl chloride, (0.5 equiv) was found to cleave the PMB group from alkyl, aryl PMB ethers, and esters to give corresponding alcohol and acid in good yields. This method offers simple and efficient protocol for the selective deprotection of PMB ether and ester in DCE at ambient temperature.

  发现草酰氯（0.5当量）可将PMB基团从烷基，芳基PMB醚和酯中裂解出来，从而以高收率得到相应的醇和酸。该方法为环境温度下DCE中PMB醚和酯的选择性脱保护提供了简单有效的方案。
• Functionalized nucleic acids and particles comprising them for the treatment of HIV infections
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2468303A1

  公开（公告）日：2012-06-27

  The present invention relates to a particle comprising a functionalized nucleic acid non-covalently associated to a cell-penetrating peptide, wherein: • the functionalized nucleic acid comprises, or consists of: - an HIV integrase-inhibiting oligonucleotide comprising from 11 to 20 contiguous nucleotides; and - at least one functionalizing group of the following formula (I) covalently linked to the oligonucleotide: • the cell-penetrating peptide comprises from 12 to 30 contiguous amino acids; • the particle is liable to be obtained by contacting the functionalized nucleic acid with the cell-penetrating peptide in a 1/5 to 1/15 molar ratio.

  本发明涉及一种包含与细胞穿透肽非共价关联的功能化核酸的颗粒，其中： - 功能化核酸包括或包含 - 由 11 至 20 个连续核苷酸组成的 HIV 整合酶抑制寡核苷酸；以及 - 与寡核苷酸共价连接的至少一个下式 (I) 的官能化基团： - 细胞穿透肽包括 12 至 30 个连续的氨基酸； - 通过将官能化核酸与细胞穿透肽以 1/5 至 1/15 的摩尔比接触，可获得颗粒。
• US4767783A
  申请人：——

  公开号：US4767783A

  公开（公告）日：1988-08-30
• Grimmer,G.; Kracht,J., Chemische Berichte, 1963, vol. 96, p. 3370 - 3373
  作者：Grimmer,G.、Kracht,J.

  DOI：——

  日期：——
• A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA₁), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration
  作者：Inés González-Gil、Debora Zian、Henar Vázquez-Villa、Gloria Hernández-Torres、R. Fernando Martínez、Nora Khiar-Fernández、Richard Rivera、Yasuyuki Kihara、Isabel Devesa、Sakthikumar Mathivanan、Cristina Rosell del Valle、Emma Zambrana-Infantes、María Puigdomenech、Giovanni Cincilla、Melchor Sanchez-Martinez、Fernando Rodríguez de Fonseca、Antonio V. Ferrer-Montiel、Jerold Chun、Rubén López-Vales、María L. López-Rodríguez、Silvia Ortega-Gutiérrez

  DOI：10.1021/acs.jmedchem.9b01287

  日期：2020.3.12

  Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA(1)) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA(1) agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA(1) receptor agonist described so far (E-max = 118%, EC50 = 0.24 mu M, KD = 19.6 nM; inactive at autotaxin and LPA(2-6) receptors). This compound induces characteristic LPA(1)-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.