1-pentyl-N-phenyl-1H-indole-3-carboxamide | 1430634-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-pentyl-N-phenyl-1H-indole-3-carboxamide
• 英文别名: N-phenyl-1-pentyl-1H-indole-3-carboxamide；Sdb-005；1-pentyl-N-phenylindole-3-carboxamide
• CAS: 1430634-87-9
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: SPUQBSMPSCYQLS-UHFFFAOYSA-N

物化性质

• 沸点：
  414.5±18.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMF:PBS (pH 7.2)(1:3)：0.25 mg/ml； DMSO：25mg/mL；乙醇：25mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,2,2-三氟-1-(1-戊基-1H-吲哚-3-基)乙烷-1-酮 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 1-pentyl-N-phenyl-1H-indole-3-carboxamide
  参考文献：
  名称：

  The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse

  摘要：

  Two novel adamantane derivatives, adamantan-1-yl (1-pentyl-1H-indo1-3-yl) methano ne (AB-001) and N-(adamtan-1-yl)-1-pentyl-1H-indole-3-carboxamide (SDB-001), were recently identified as cannabimimetic indoles of abuse. Conflicting anecdotal reports of the psychoactivity of AB-001 in humans, and a complete dearth of information about the bioactivity of SDB-001, prompted the preparation of AB-001, SDB-001, and several analogues intended to explore preliminary structure-activity relationships within this class. This study sought to elucidate which structural features of AB-001, SDB-001, and their analogues govern the cannabimimetic potency of these chemotypes in vitro and in vivo. All compounds showed similar full agonist profiles at CB1 (EC50 = 16-43 nM) and CB2 (EC50 = 29-216 nM) receptors in vitro using a FLIPR membrane potential assay, with the exception of SDB-002, which demonstrated partial agonist activity at CB2 receptors. The activity of AB-001, AB-002, and SDB-001 in rats was compared to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC) and cannabimimetic indole JWH-018 using biotelemetry. SDB-001 dose-dependently induced hypothermia and reduced heart rate (maximal dose 10 mg/kg) with potency comparable to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC, maximal dose 10 mg/kg), and lower than that of JWH-018 (maximal dose 3 mg/kg). Additionally, the changes in body temperature and heart rate affected by SDB-001 are of longer duration than those of Delta(9)-THC or JWH-018, suggesting a different pharmacokinetic profile. In contrast, AB-001, and its homologue, AB-002, did not produce significant hypothermic and bradycardic effects, even at relatively higher doses (up to 30 mg/kg), indicating greatly reduced potency compared to Delta(9)-THC, JWH-018, and SDB-001.

  DOI：

  10.1021/cn400035r

文献信息

• The Synthesis and Pharmacological Evaluation of Adamantane-Derived Indoles: Cannabimimetic Drugs of Abuse
  作者：Samuel D. Banister、Shane M. Wilkinson、Mitchell Longworth、Jordyn Stuart、Nadine Apetz、Katrina English、Lance Brooker、Catrin Goebel、David E. Hibbs、Michelle Glass、Mark Connor、Iain S. McGregor、Michael Kassiou

  DOI：10.1021/cn400035r

  日期：2013.7.17

  Two novel adamantane derivatives, adamantan-1-yl (1-pentyl-1H-indo1-3-yl) methano ne (AB-001) and N-(adamtan-1-yl)-1-pentyl-1H-indole-3-carboxamide (SDB-001), were recently identified as cannabimimetic indoles of abuse. Conflicting anecdotal reports of the psychoactivity of AB-001 in humans, and a complete dearth of information about the bioactivity of SDB-001, prompted the preparation of AB-001, SDB-001, and several analogues intended to explore preliminary structure-activity relationships within this class. This study sought to elucidate which structural features of AB-001, SDB-001, and their analogues govern the cannabimimetic potency of these chemotypes in vitro and in vivo. All compounds showed similar full agonist profiles at CB1 (EC50 = 16-43 nM) and CB2 (EC50 = 29-216 nM) receptors in vitro using a FLIPR membrane potential assay, with the exception of SDB-002, which demonstrated partial agonist activity at CB2 receptors. The activity of AB-001, AB-002, and SDB-001 in rats was compared to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC) and cannabimimetic indole JWH-018 using biotelemetry. SDB-001 dose-dependently induced hypothermia and reduced heart rate (maximal dose 10 mg/kg) with potency comparable to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC, maximal dose 10 mg/kg), and lower than that of JWH-018 (maximal dose 3 mg/kg). Additionally, the changes in body temperature and heart rate affected by SDB-001 are of longer duration than those of Delta(9)-THC or JWH-018, suggesting a different pharmacokinetic profile. In contrast, AB-001, and its homologue, AB-002, did not produce significant hypothermic and bradycardic effects, even at relatively higher doses (up to 30 mg/kg), indicating greatly reduced potency compared to Delta(9)-THC, JWH-018, and SDB-001.