(1S)-3-(2-cyclohexylethyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (1S)-3-(2-cyclohexylethyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane
• 英文别名: (S)-3-(2-Cyclohexyl-ethyl)-1,8,8-trimethyl-3-aza-bicyclo[3.2.1]octane
• 化学式: C₁₈H₃₃N
• 分子量: 263.467
• InChiKey: UJFYUKXOMXZHHF-UHUGOGIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环己基乙酸 在 lithium aluminium tetrahydride 作用下， 生成 (1S)-3-(2-cyclohexylethyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  An aromatic moiety is not essential for pharmacophore binding to sigma binding sites: Synthesis of N-alkylazacycloheptane derivatives as potent sigma ligands

  摘要：

  Novel 3-(omega-(cycloalkyl)-alkyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octanes that had no aromatic rings were synthesized. Binding studies showed that these compounds were potent sigma ligands. Due to their simple structures without extra functional groups, they are suitable tools with which to identify pharmacophores capable of binding strongly to sigma binding sites. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00417-4

文献信息

• AZEPINE DERIVATIVE, PRODUCTION THEREOF, AND USE THEREOF
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0661271A1

  公开（公告）日：1995-07-05

  An azepine derivative represented by general formula (1) or a nontoxic salt thereof, a process for producing the same, and a therapeutic agent containing the same as the active ingredient for treating diseases related to σ-receptor, wherein R represents a group represented by general formula (2) (wherein R¹ represents hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen or optionally substituted phenyl, and n represents 0 or 1), C₅-C₈ cycloalkyl which may be substituted by lower alkyl, norbornyl, bicyclo[3.3.1]nonyl, naphthyl, 1,3-benzodioxolyl, pyridyl or thienyl; m represents an integer of 0 to 4; and C* represents an asymmetric carbon atom. The compound (1) and nontoxic salt thereof have a high affinity for σ-receptor but scarcely any affinity for other receptors, thus being utilized for treating diseases related to σ-receptor, such as schizophrenia.

  通式(1)代表的氮杂环庚烷衍生物或其无毒盐，生产该衍生物的工艺，以及含有该衍生物作为活性成分的治疗剂，用于治疗与σ-受体有关的疾病、其中 R 代表通式 (2) 所代表的基团（其中 R¹ 代表氢、低级烷基、低级烷氧基、羟基、卤素或任选取代的苯基，且 n 代表 0 或 1）、可被低级烷基取代的 C₅-C₈ 环烷基、降冰片烷基、双环[3.3.1]壬基、萘基、1,3-苯并二恶茂基、吡啶基或噻吩基；m 代表 0 至 4 的整数；C* 代表不对称碳原子。化合物(1)及其无毒盐对σ受体有很高的亲和力，但对其他受体几乎没有亲和力，因此可用于治疗与σ受体有关的疾病，如精神分裂症。
• AZEPINE DERIVATIVES, PRODUCTION THEREOF, AND USE THEREOF AS SIGMA-RECEPTOR LIGANDS
  申请人：Asahi Kasei Kogyo Kabushiki Kaisha

  公开号：EP0661271B1

  公开（公告）日：2000-04-26
• US5658923A
  申请人：——

  公开号：US5658923A

  公开（公告）日：1997-08-19
• An aromatic moiety is not essential for pharmacophore binding to sigma binding sites: Synthesis of N-alkylazacycloheptane derivatives as potent sigma ligands
  作者：Akitake Yamashita、Nobuyuki Takahashi、Daisuke Mochizuki、Ryuichi Tsujita、Shinji Yamada、Hiromu Kawakubo、Yukio Suzuki、Hideyuki Watanabe

  DOI：10.1016/s0960-894x(97)00417-4

  日期：1997.9

  Novel 3-(omega-(cycloalkyl)-alkyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octanes that had no aromatic rings were synthesized. Binding studies showed that these compounds were potent sigma ligands. Due to their simple structures without extra functional groups, they are suitable tools with which to identify pharmacophores capable of binding strongly to sigma binding sites. (C) 1997 Elsevier Science Ltd.