URB447 | 1132922-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: URB447
• 英文别名: (4-amino-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl)(phenyl)methanone；[4-amino-1-[(4-chlorophenyl)methyl]-2-methyl-5-phenyl-1H-pyrrol-3-yl]phenylmethanone；[4-amino-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrole-3-yl](phenyl)methanone；{4-Amino-1-[(4-chlorophenyl)methyl]-2-methyl-5-phenyl-1H-pyrrol-3-yl}(phenyl)methanone；[4-amino-1-[(4-chlorophenyl)methyl]-2-methyl-5-phenylpyrrol-3-yl]-phenylmethanone
• CAS: 1132922-57-6
• 化学式: C₂₅H₂₁ClN₂O
• 分子量: 400.908
• InChiKey: KGXYGMKEFDUWNB-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  568.6±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：10mg/mL； DMSO：10mg/mL；乙醇：10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  48
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-phenyl-3-chloro-2-buten-1-one 在 4-二甲氨基吡啶 、 sodium azide 、 高氯酸 、 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.0h， 生成 URB447
  参考文献：
  名称：

  RhII催化[3 + 2]与N-磺酰基-1,2,3-三唑的2 H-叠氮基环加成

  摘要：

  Rh II催化的2 H-叠氮基与N-磺酰基-1,2,3-三唑的分子间[3 + 2]环加成反应 ，其中通过氮杂乙烯基卡宾铑中间体生产了一系列功能完全的吡咯。该反应的显着特征是，氮杂乙烯基卡宾可作为[2 C]等效物，而不是先前在环丙烷和[3+ n ]环加成中报道的[1 C]或aza- [3 C]合成子。。此外，该方法学也已成功应用于URB447的全合成以及阿托伐他汀（立普妥）的正式合成。

  DOI：

  10.1002/chem.201406460

文献信息

• Synthesis and characterization of a peripherally restricted CB1 cannabinoid antagonist, URB447, that reduces feeding and body-weight gain in mice
  作者：Jesse LoVerme、Andrea Duranti、Andrea Tontini、Gilberto Spadoni、Marco Mor、Silvia Rivara、Nephi Stella、Cong Xu、Giorgio Tarzia、Daniele Piomelli

  DOI：10.1016/j.bmcl.2008.12.059

  日期：2009.2

  Cannabinoid CB1 receptor antagonists reduce body weight in rodents and humans, but their clinical utility as anti-obesity agents is limited by centrally mediated side effects. Here, we describe the first mixed CB1 antagonist/CB2 agonist, URB447 ([4-amino-1-(4-chlorobenzyl)-2-methyl-5-phenyl-1H-pyrrol-3-yl]( phenyl) methanone), which lowers food intake and body-weight gain in mice without entering the brain or antagonizing central CB1-dependent responses. URB447 may provide a useful pharmacological tool for investigating the cannabinoid system, and might serve as a starting point for developing clinically viable CB1 antagonists devoid of central side effects. (c) 2009 Elsevier Ltd. All rights reserved.
• 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.
• Rh^II-Catalyzed [3+2] Cycloaddition of 2 <i>H</i>-Azirines with<i>N</i>-Sulfonyl-1,2,3-Triazoles
  作者：Yun-Zhou Zhao、Hai-Bin Yang、Xiang-Ying Tang、Min Shi

  DOI：10.1002/chem.201406460

  日期：2015.2.23

  RhII‐catalyzed intermolecular [3+2] cycloaddition of 2 H‐azirines with N‐sulfonyl‐1,2,3‐triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza‐[3 C] synthons, which have been reported previously in cyclopropanations

  Rh II催化的2 H-叠氮基与N-磺酰基-1,2,3-三唑的分子间[3 + 2]环加成反应 ，其中通过氮杂乙烯基卡宾铑中间体生产了一系列功能完全的吡咯。该反应的显着特征是，氮杂乙烯基卡宾可作为[2 C]等效物，而不是先前在环丙烷和[3+ n ]环加成中报道的[1 C]或aza- [3 C]合成子。。此外，该方法学也已成功应用于URB447的全合成以及阿托伐他汀（立普妥）的正式合成。