1-[1-(1-methylcyclooctyl)piperidin-4-yl]-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazole | 1108147-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-[1-(1-methylcyclooctyl)piperidin-4-yl]-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazole
• 英文别名: 1-[1-(1-methylcyclooctyl)piperidin-4-yl]-2-[3-(trifluoromethyl)phenyl]benzimidazole
• CAS: 1108147-82-5
• 化学式: C₂₈H₃₄F₃N₃
• 分子量: 469.593
• InChiKey: HQBSTEJSIZHCBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[1-(1-methylcyclooctyl)piperidin-4-yl]-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazole 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Novel Non-Peptide Nociceptin/Orphanin FQ Receptor Agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: Design, Synthesis, and Structure−Activity Relationship of Oral Receptor Occupancy in the Brain for Orally Potent Antianxiety Drug

  摘要：

  An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus, the N/OFQ and NOP receptor are located in the central nervous systems in humans, primates, and rodents, and are involved in the integration of the emotional components in the brain; e.g., N/OFQ displays anxiolytic activity in the brain. For identifying orally potent anxiolytic, drug-design studies were performed with a series of 1,2-disubstituted benzimidazole derivatives, which resulted in the identification of various chemotypes of highly potent NOP selective full agonists in vitro with high or moderate NOP receptor occupancy in the mice brain per os such as 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1-H-benzimidazole 1 (MCOPPB), the most potent novel non-peptide NOP full agonist in vitro and an orally potent anxiolytic in the mice.

  DOI：

  10.1021/jm7012979
• 作为产物：
  描述：

  N-[1-(1-methylcyclooctyl)-4-piperidinyl]-1,2-benzenediamine 、 3-(三氟甲基)苯甲酰氯 在 吡啶 、 phosphoryl trichloride 作用下， 反应 4.5h， 以21%的产率得到1-[1-(1-methylcyclooctyl)piperidin-4-yl]-2-[3-(trifluoromethyl)phenyl]-1H-benzimidazole
  参考文献：
  名称：

  Novel Non-Peptide Nociceptin/Orphanin FQ Receptor Agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1H-benzimidazole: Design, Synthesis, and Structure−Activity Relationship of Oral Receptor Occupancy in the Brain for Orally Potent Antianxiety Drug

  摘要：

  An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus, the N/OFQ and NOP receptor are located in the central nervous systems in humans, primates, and rodents, and are involved in the integration of the emotional components in the brain; e.g., N/OFQ displays anxiolytic activity in the brain. For identifying orally potent anxiolytic, drug-design studies were performed with a series of 1,2-disubstituted benzimidazole derivatives, which resulted in the identification of various chemotypes of highly potent NOP selective full agonists in vitro with high or moderate NOP receptor occupancy in the mice brain per os such as 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1-H-benzimidazole 1 (MCOPPB), the most potent novel non-peptide NOP full agonist in vitro and an orally potent anxiolytic in the mice.

  DOI：

  10.1021/jm7012979

文献信息

• Novel Non-Peptide Nociceptin/Orphanin FQ Receptor Agonist, 1-[1-(1-Methylcyclooctyl)-4-piperidinyl]-2-[(3<i>R</i>)-3-piperidinyl]-1<i>H</i>-benzimidazole: Design, Synthesis, and Structure−Activity Relationship of Oral Receptor Occupancy in the Brain for Orally Potent Antianxiety Drug
  作者：Shigeo Hayashi、Akiko Hirao、Aki Imai、Hiroshi Nakamura、Yoshinori Murata、Katsuyo Ohashi、Eriko Nakata

  DOI：10.1021/jm7012979

  日期：2009.2.12

  An endogenous heptadecapeptide, nociceptin/orphanin FQ (N/OFQ), and a G-protein-coupled receptor, N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], have been described in terms of its structure, distribution, and pharmacology. Thus, the N/OFQ and NOP receptor are located in the central nervous systems in humans, primates, and rodents, and are involved in the integration of the emotional components in the brain; e.g., N/OFQ displays anxiolytic activity in the brain. For identifying orally potent anxiolytic, drug-design studies were performed with a series of 1,2-disubstituted benzimidazole derivatives, which resulted in the identification of various chemotypes of highly potent NOP selective full agonists in vitro with high or moderate NOP receptor occupancy in the mice brain per os such as 1-[1-(1-methylcyclooctyl)-4-piperidinyl]-2-[(3R)-3-piperidinyl]-1-H-benzimidazole 1 (MCOPPB), the most potent novel non-peptide NOP full agonist in vitro and an orally potent anxiolytic in the mice.