3-Ethyl-5-phenyl-1,2,3,4,5-pentahydroazepino[4,5-b]benzothiophene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-Ethyl-5-phenyl-1,2,3,4,5-pentahydroazepino[4,5-b]benzothiophene
• 英文别名: 7-Ethyl-9-phenyl-6,7,8,9-tetrahydro-5H-10-thia-7-aza-benzo[a]azulene；3-ethyl-5-phenyl-1,2,4,5-tetrahydro-[1]benzothiolo[2,3-d]azepine
• 化学式: C₂₀H₂₁NS
• 分子量: 307.459
• InChiKey: QSIVEZLJXIOJFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  31.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(苯并[b]噻吩-3-基)乙胺 在 盐酸 、 硼烷四氢呋喃络合物 、 硫酸 、 三氟乙酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 3-Ethyl-5-phenyl-1,2,3,4,5-pentahydroazepino[4,5-b]benzothiophene
  参考文献：
  名称：

  Modified Ibogaine Fragments:  Synthesis and Preliminary Pharmacological Characterization of 3-Ethyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]benzothiophenes

  摘要：

  Five phenyl-substituted derivatives and analogues of 1,2,3,4,5,6-hexahydroazepino[4,5-b]indol 5, a major fragment of ibogaine (1), were synthesized and tested for binding to monoamine transporters, the NMDA receptor-coupled cation channel, and dopamine and opioid receptors. All five derivatives, 9 and 17a-d, displayed 8-10-fold higher affinity at the DA transporter than ibogaine and noribogaine (4). At the serotonin transporter,: two compounds (9 and 17a) exhibited higher potency than ibogaine, while the rest had weaker binding affinities than the lead compound. In keeping with their structural similarity to ibogaine, all five compounds displayed weak to poor affinity for dopamine D1 and D2 receptors. However, two compounds, 17a,c, demonstrated moderate binding affinities at dopamine D3 receptors. All five compounds displayed weak to poor affinities for mu and kappa opioid receptors and for the NMDA receptor-coupled cation channel. Despite the qualitative differences, derivatives and analogues of 5 may serve as useful substitutes for ibogaine.

  DOI：

  10.1021/jm980156y

文献信息

• TRICYCLIC IBOGAINE ANALOGS, THEIR PREPARATION AND THEIR USE IN TREATING SUBSTANCE ABUSE
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：EP0910567A1

  公开（公告）日：1999-04-28
• US5616575A
  申请人：——

  公开号：US5616575A

  公开（公告）日：1997-04-01
• [EN] TRICYCLIC IBOGAINE ANALOGS, THEIR PREPARATION AND THEIR USE IN TREATING SUBSTANCE ABUSE<br/>[FR] ANALOGUES D'IBOGAINE TRICYCLIQUES, LEUR PREPARATION ET LEUR UTILISATION POUR TRAITER LA TOXICOMANIE
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：WO1997020847A1

  公开（公告）日：1997-06-12

  (EN) The present invention provides a series of ibogaine analogs of formula (I) wherein: R1 is S or O; R2 is H, (C1-C4)alkyl, (C1-C4)alkoxy, OH, CN, CONH2, halo, oxazolyl, (C1-C4)alkylS, or (C1-C2)trifluoroalkyl; R3 is a phenyl group optionally substituted at the 2'- or 3'-position of the phenyl ring with halo, N(R)2, wherein each R is H or (C1-C4)alkyl; or NO2; and R4 is (C3-C6)cycloalkyl(C1-C4)alkyl, (C3-C6)cycloalkyl or (C1-C4)alkyl, optionally containing 1-2 double bonds, and the pharmaceutically acceptable salts thereof, useful to treat cocaine addiction and the use of other addictive substances.(FR) Série d'analogues d'ibogaïne de formule (I) dans laquelle R1 est S ou O; R2 est H, alkyle (C1-C4), alcoxy (C1-C4), OH, CN, CONH2, halo, oxazolyle, alkyls (C1-C4) ou trifluoroalkyle (C1-C2); R3 est un groupe phényle éventuellement substitué en position 2' ou 3' du cycle phényle avec halo, N(R)2, chaque R étant H ou alkyle (C1-C4); ou NO2; et R4 est cycloalkyle (C3-C6)-alkyle (C1-C4), cycloalkyle (C3-C6) ou alkyle (C1-C4), contenant éventuellement 1 ou 2 liaisons doubles, ainsi que sels pharmaceutiquement acceptables desdits analogues, utiles pour traiter la dépendance à la cocaïne et l'utilisation d'autres substances créant l'accoutumance.
• Modified Ibogaine Fragments:  Synthesis and Preliminary Pharmacological Characterization of 3-Ethyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-<i>b</i>]benzothiophenes
  作者：Simon M. N. Efange、Deborah C. Mash、Anil B. Khare、Quinjie Ouyang

  DOI：10.1021/jm980156y

  日期：1998.11.1

  Five phenyl-substituted derivatives and analogues of 1,2,3,4,5,6-hexahydroazepino[4,5-b]indol 5, a major fragment of ibogaine (1), were synthesized and tested for binding to monoamine transporters, the NMDA receptor-coupled cation channel, and dopamine and opioid receptors. All five derivatives, 9 and 17a-d, displayed 8-10-fold higher affinity at the DA transporter than ibogaine and noribogaine (4). At the serotonin transporter,: two compounds (9 and 17a) exhibited higher potency than ibogaine, while the rest had weaker binding affinities than the lead compound. In keeping with their structural similarity to ibogaine, all five compounds displayed weak to poor affinity for dopamine D1 and D2 receptors. However, two compounds, 17a,c, demonstrated moderate binding affinities at dopamine D3 receptors. All five compounds displayed weak to poor affinities for mu and kappa opioid receptors and for the NMDA receptor-coupled cation channel. Despite the qualitative differences, derivatives and analogues of 5 may serve as useful substitutes for ibogaine.