[1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]-2-naphthalenylmethanone | 133438-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]-2-naphthalenylmethanone
• 英文别名: JWH 200 2'-naphthyl isomer；[1-(2-morpholin-4-ylethyl)indol-3-yl]-naphthalen-2-ylmethanone
• CAS: 133438-66-1
• 化学式: C₂₅H₂₄N₂O₂
• 分子量: 384.478
• InChiKey: ZESGOIBULDUMRS-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMF：0.30 mg/ml；二甲基亚砜：0.15 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-萘甲酸 在 氯化亚砜 、 二氯乙基铝 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 [1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]-2-naphthalenylmethanone
  参考文献：
  名称：

  Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics

  摘要：

  Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands. In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of [H-3]Win 55212-2 (5). Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists. The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (II) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position. A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist. Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids. The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid. Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).

  DOI：

  10.1021/jm00016a013

文献信息

• CANNABINOIDS AND DERIVATIVES FOR PROMOTING IMMUNOGENICITY OF TUMOR AND INFECTED CELLS
  申请人：Pascal Biosciences Inc.

  公开号：EP3743061A1

  公开（公告）日：2020-12-02
• [EN] CANNABINOIDS AND DERIVATIVES FOR PROMOTING IMMUNOGENICITY OF TUMOR AND INFECTED CELLS<br/>[FR] CANNABINOÏDES ET LEURS DÉRIVÉS POUR FAVORISER L'IMMUNOGÉNICITÉ DES CELLULES TUMORALES ET INFECTÉES
  申请人：PASCAL BIOSCIENCES INC

  公开号：WO2019144126A1

  公开（公告）日：2019-07-25

  This invention provides processes and compositions for enhancing the immunogenicity of tumor or infected cells by increasing expression of major histocompatibility complex (MHC) class I surface molecules. Tumor cells often circumvent immune recognition by reducing or eliminating MHC expression. The lack of MHC on their surface allows tumor cells to evade immune detection and enables uncontrolled growth. Similarly, certain viral or microbial infections result in MHC class I downregulation and the resulting immune evasion. With a unique reporter assay, we have determined that some cannabinoid compounds and structural analogs can increase MHC class I expression on tumor cells grown in cell culture. The increase of tumor and infected cell MHC class I expression will enable detection and destruction by cytotoxic T-lymphocyte cells. The process and compositions increase the immunogenicity of the target cells, e.g. tumor or infected cells, to enhance their destruction by cytotoxic lymphocytes. When administered in combination, such compositions may enhance the activity of immune- oncology and anti-infectious disease agents.
• Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics
  作者：Michael A. Eissenstat、Malcolm R. Bell、Thomas E. D'Ambra、E. John Alexander、Sol J. Daum、James H. Ackerman、Monte D. Gruett、Virendra Kumar、Kimberly G. Estep

  DOI：10.1021/jm00016a013

  日期：1995.8

  Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands. In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of [H-3]Win 55212-2 (5). Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists. The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (II) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position. A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist. Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids. The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid. Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).