1-butyl-7-methoxy-3-(naphthalen-2-yl)-1H-indole | 1438278-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-butyl-7-methoxy-3-(naphthalen-2-yl)-1H-indole
• 英文别名: 1-Butyl-7-methoxy-3-naphthalen-2-ylindole；1-butyl-7-methoxy-3-naphthalen-2-ylindole
• CAS: 1438278-48-8
• 化学式: C₂₃H₂₃NO
• 分子量: 329.442
• InChiKey: MDEZNAJVPGRYNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-butyl-7-methoxy-3-(naphthalen-2-yl)-1H-indole 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以52%的产率得到1-butyl-3-(naphthalen-2-yl)-1H-indol-7-ol
  参考文献：
  名称：

  Synthesis of carbon-11-labeled aminoalkylindole derivatives as new candidates of cannabinoid receptor radioligands for PET imaging of alcohol abuse

  摘要：

  Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[C-11] methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([C-11]3), 1-butyl-7-[C-11]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([C-11]5), and 1-butyl-7-[C-11]methoxy-3-(naphthalene-2-yl)-1H-indole ([C-11]8) were prepared by O-[C-11]methylation of their corresponding precursors with [C-11]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/mu mol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.097
• 作为产物：
  描述：

  7-甲氧基吲哚 在 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 potassium hydroxide 、 2-(二环己基膦基)联苯 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 1.42h， 生成 1-butyl-7-methoxy-3-(naphthalen-2-yl)-1H-indole
  参考文献：
  名称：

  Synthesis of carbon-11-labeled aminoalkylindole derivatives as new candidates of cannabinoid receptor radioligands for PET imaging of alcohol abuse

  摘要：

  Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[C-11] methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([C-11]3), 1-butyl-7-[C-11]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([C-11]5), and 1-butyl-7-[C-11]methoxy-3-(naphthalene-2-yl)-1H-indole ([C-11]8) were prepared by O-[C-11]methylation of their corresponding precursors with [C-11]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/mu mol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.097

文献信息

• [EN] USE OF THE AMINOALKYLINDOLE JWH-073-M4 AND RELATED COMPOUNDS AS NEUTRAL CB1 RECPTOR ANTAGONISTS FOR THE TREATMENT OF ALCOHOLISM, DRUG ABUSE, OBESITY, AND OBESITY-RELATED DISEASES<br/>[FR] UTILISATION DE L'AMINOALKYLINDOLE JWH-073-M4 ET COMPOSÉS APPARENTÉS COMME ANTAGONISTES NEUTRES DES RÉCEPTEURS AUX CANNABINOÏDES DE TYPE 1 POUR LE TRAITEMENT DE L'ALCOOLISME, DE L'ABUS DE DROGUES, DE L'OBÉSITÉ ET DES MALADIES LIÉES À L'OBÉSITÉ
  申请人：UNIV ARKANSAS

  公开号：WO2013106349A1

  公开（公告）日：2013-07-18

  Novel alkylindoles that bind tightly to cannabinoid receptors and are neutral antagonists for the cannabinoid 1 receptor and agonists for the cannabinoid 2 receptor are provided. These compounds are useful for treating alcoholism and drug abuse and for treating obesity.

  提供了一种新型烷基吲哚化合物，它们与大麻素受体结合紧密，是大麻素1受体的中性拮抗剂和大麻素2受体的激动剂。这些化合物对治疗酗酒和药物滥用以及治疗肥胖症是有用的。
• USE OF THE AMINOALKYLINDOLE JWH-073-M4 AND RELATED COMPOUNDS AS NEUTRAL CB1 RECPTOR ANTAGONISTS FOR THE TREATMENT OF ALCOHOLISM, DRUG ABUSE, OBESITY, AND OBESITY-RELATED DISEASES
  申请人：The Board of Trustees of the University of Arkansas

  公开号：US20150266820A1

  公开（公告）日：2015-09-24

  Novel alkylindoles that bind tightly to cannabinoid receptors and are neutral antagonists for the cannabinoid 1 receptor and agonists for the cannabinoid 2 receptor are provided. These compounds are useful for treating alcoholism and drug abuse and for treating obesity.

  提供了一种新型烷基吲哚化合物，它们能够紧密结合大麻素受体，并且是大麻素1受体的中性拮抗剂和大麻素2受体的激动剂。这些化合物可用于治疗酗酒和药物滥用以及治疗肥胖症。
• Design, Synthesis, and Biological Evaluation of Aminoalkylindole Derivatives as Cannabinoid Receptor Ligands with Potential for Treatment of Alcohol Abuse
  作者：Tamara Vasiljevik、Lirit N. Franks、Benjamin M. Ford、Justin T. Douglas、Paul L. Prather、William E. Fantegrossi、Thomas E. Prisinzano

  DOI：10.1021/jm400268b

  日期：2013.6.13

  Attenuation of increased endocannabinoid signaling with a CB1R neutral antagonist might offer a new therapeutic direction for treatment of alcohol abuse. We have recently reported that a monohydroxylated metabolite of the synthetic aminoalkylindole cannabinoid JHW-073 (3) exhibits neutral antagonist activity at CB1Rs and thus may serve as a promising lead for the development of novel alcohol abuse therapies. In the current study, we show that systematic modification of an aminoalkylindole scaffold identified two new compounds with dual CB1R antagonist/CB2R agonist activity. Similar to the CB1R antagonist/inverse agonist rimonabant, analogues 27 and 30 decrease oral alcohol self-administration without affecting total fluid intake and block the development of alcohol-conditioned place preference. Collectively, these initial findings suggest that design and systematic modification of aminoalkylindoles such as 3 may lead to development of novel cannabinoid ligands with dual CB1R antagonist/CB2R agonist activity with potential for use as treatments of alcohol abuse.
• US9416103B2
  申请人：——

  公开号：US9416103B2

  公开（公告）日：2016-08-16
• Synthesis of carbon-11-labeled aminoalkylindole derivatives as new candidates of cannabinoid receptor radioligands for PET imaging of alcohol abuse
  作者：Mingzhang Gao、Andy Chufan Gao、Min Wang、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2014.10.097

  日期：2014.12

  Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[C-11] methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([C-11]3), 1-butyl-7-[C-11]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([C-11]5), and 1-butyl-7-[C-11]methoxy-3-(naphthalene-2-yl)-1H-indole ([C-11]8) were prepared by O-[C-11]methylation of their corresponding precursors with [C-11]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/mu mol. (C) 2014 Elsevier Ltd. All rights reserved.