5-(5-Hydroxypentyl)-1,3-benzenediol

• 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: 5-(5-Hydroxypentyl)-1,3-benzenediol
• 英文别名: 5-(5-hydroxypentyl)benzene-1,3-diol
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: UFALVEWFBVEVIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(5-Hydroxypentyl)-1,3-benzenediol 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以10 g的产率得到5''-Hydroxy-cannabidiol
  参考文献：
  名称：

  [EN] CANNABIDIOL-CONTAINING COMPOSITIONS AND USES THEREOF
  [FR] COMPOSITIONS CONTENANT DU CANNABIDIOL ET LEURS UTILISATIONS

  摘要：

  提供了包含与大麻二酚（CBD）相关的细胞衍生颗粒的组合物，并且提供了这些组合物在治疗可以从大麻二酚（CBD）中受益的医疗状况中的用途。

  公开号：

  WO2021205459A1
• 作为产物：
  描述：

  5-(3,5-二甲氧基苯基)戊酸乙酯 在 lithium aluminium tetrahydride 、 氢溴酸 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成 5-(5-Hydroxypentyl)-1,3-benzenediol
  参考文献：
  名称：

  Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability

  摘要：

  Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious neurological disorder that occurs in patients with cirrhosis or liver failure. Although cannabidiol is effective in models of HE, it has limitations in terms of safety and oral bioavailability. Herein, we describe a series of side chain modified resorcinols that were designed for greater hydrophilicity and "drug likeness", while varying hydrogen bond donors, acceptors, architecture, basicity, neutrality, acidity, and polar surface area within the pendent group. Our primary screen evaluated the ability of the test agents to prevent damage to hippocampal neurons induced by ammonium acetate and ethanol at clinically relevant concentrations. Notably, KLS-13019 was 50-fold more potent and >400-fold safer than cannabidiol and exhibited an in vitro profile consistent with improved oral bioavailability.

  DOI：

  10.1021/acsmedchemlett.6b00009

文献信息

• [EN] MODIFIED CANNABINOIDS AND USES THEREOF<br/>[FR] CANNABINOÏDES MODIFIÉS ET LEURS UTILISATIONS
  申请人：UNIV RAMOT

  公开号：WO2022215078A1

  公开（公告）日：2022-10-13

  The present disclosure provides cannabidiol (CBD)-phospholipid conjugates, designed so as not to interfere with the interaction of the CBD with its CB receptor, cell-derived particles (e.g., extracellular vesicles) associated with these conjugates and uses thereof are provided.

  本公开提供了大麻二酚（CBD）-磷脂共轭物，设计为不干扰CBD与其CB受体的相互作用，并提供与这些共轭物相关的细胞衍生颗粒（例如细胞外囊泡）以及其用途。
• Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability
  作者：William A. Kinney、Mark E. McDonnell、Hua Marlon Zhong、Chaomin Liu、Lanyi Yang、Wei Ling、Tao Qian、Yu Chen、Zhijie Cai、Dean Petkanas、Douglas E. Brenneman

  DOI：10.1021/acsmedchemlett.6b00009

  日期：2016.4.14

  Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious neurological disorder that occurs in patients with cirrhosis or liver failure. Although cannabidiol is effective in models of HE, it has limitations in terms of safety and oral bioavailability. Herein, we describe a series of side chain modified resorcinols that were designed for greater hydrophilicity and "drug likeness", while varying hydrogen bond donors, acceptors, architecture, basicity, neutrality, acidity, and polar surface area within the pendent group. Our primary screen evaluated the ability of the test agents to prevent damage to hippocampal neurons induced by ammonium acetate and ethanol at clinically relevant concentrations. Notably, KLS-13019 was 50-fold more potent and >400-fold safer than cannabidiol and exhibited an in vitro profile consistent with improved oral bioavailability.
• [EN] CANNABIDIOL-CONTAINING COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSITIONS CONTENANT DU CANNABIDIOL ET LEURS UTILISATIONS
  申请人：UNIV RAMOT

  公开号：WO2021205459A1

  公开（公告）日：2021-10-14

  Compositions comprising a cell-derived particle associated with Cannabidiol (CBD), and uses thereof in treating medical conditions that can benefit from Cannabidiol (CBD) are provided.

  提供了包含与大麻二酚（CBD）相关的细胞衍生颗粒的组合物，并且提供了这些组合物在治疗可以从大麻二酚（CBD）中受益的医疗状况中的用途。