9-phenylnon-8-enoic acid | 207132-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 9-phenylnon-8-enoic acid
• CAS: 207132-52-3
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: JCNDPUHPQFZEMT-UHFFFAOYSA-N

物化性质

• 沸点：
  404.8±34.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  9-phenylnon-8-enoic acid 在 10% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以53%的产率得到9-苯基壬酸
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationship of Fatty Acid Amide Hydrolase Inhibitors: Modulation at the N-Portion of Biphenyl-3-yl Alkylcarbamates

  摘要：

  Alkylcarbamic acid biphenyl-3-yl esters are a class of fatty acid amide hydrolase (FAAH) inhibitors that comprises cyclohexylcarbamic acid 3'-carbamoylbiphenyl-3-yl ester (URB597), a compound with analgesic, anxiolytic-like and antidepressant-like properties in rat and mouse models. Here, we extended the structure-activity relationships (SARs) for this class of compounds by replacing the cyclohexyl ring of the parent compound cyclohexylcarbamic acid biphenyl-3-yl ester (URB524) (FAAH IC50 = 63 nM) with a selected set of substituents of different size, shape, flexibility, and lipophilicity. Docking experiments and linear interaction energy (LIE) calculations indicated that the N-terminal group of O-arylcarbamates fits within the lipophilic region of the substrate-binding site, mimicking the arachidonoyl chain of anandamide. Significant potency improvements were observed for the beta-naphthylmethyl derivative 4q (IC50 = 5.3 nM) and its 3'-carbamoylbiphenyl-3-yl ester 4z (URB880, IC50 = 0.63 nM), indicating that shape complementarity and hydrogen bonds are crucial to obtain highly potent inhibitors.

  DOI：

  10.1021/jm701631z
• 作为产物：
  描述：

  8-溴辛酸 在 CH₃-SO-CH₂Na 作用下， 以 二甲基亚砜 为溶剂， 反应 6.25h， 生成 9-phenylnon-8-enoic acid
  参考文献：
  名称：

  Development of an Enzyme-Linked Immunosorbent Assay for the Determination of the Linear Alkylbenzene Sulfonates and Long-Chain Sulfophenyl Carboxylates Using Antibodies Generated by Pseudoheterologous Immunization

  摘要：

  已经开发出 ELISA 方法来筛查直链烷基苯磺酸盐 (LAS) 或最直接的降解产物长链磺基苯磺酸盐 (SPC) 对水资源的污染。该测定使用通过伪异源免疫策略产生的抗体，使用通过偶联 N-(4-烷基苯基)磺酰基-3-氨基丙酸 (SFA) 和 p-( 1-羧基-13-十三烷基)苯磺酸 (13C13-SPC) 生成匙孔血蓝蛋白 (KLH)。免疫半抗原被设计用于识别分子的两个不同表位。 SFA 半抗原最大限度地识别烷基部分，同时保留 LAS 技术混合物中存在的不同烷基链的复杂性。 13C13-SPC 半抗原可识别常见且高抗原性的苯磺酸基团。使用这种策略产生的抗血清已被证明优于使用单一物质通过同源免疫程序获得的抗血清。通过使用间接 ELISA 格式，可以分别检测低至 1.8 和 0.2 μg L-1 的 LAS 和长链 SPC。测定内和测定间的变异系数分别为 6% 和 12%，证明了免疫测定的重现性。该测定可用于具有广泛 pH 值和离子强度值的介质。为评估基质效应而进行的初步实验已证明该方法作为筛选工具的潜在适用性，以评估天然水样中这些类型的表面活性剂的污染。

  DOI：

  10.1021/ac051141s

文献信息

• 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.
• Design and synthesis of novel pipernonaline derivatives as anti-austerity agents against human pancreatic cancer PANC-1 cells
  作者：Takuya Okada、Yuri Chino、Keita Yokoyama、Yuki Fujihashi、Nguyễn Duy Phan、Juthamart Maneenet、Lanke Prudhvi、Suresh Awale、Naoki Toyooka

  DOI：10.1016/j.bmc.2022.116963

  日期：2022.10