1-(3-(dimethylamino)propyl)-1H-indol-5-amine | 1202869-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(3-(dimethylamino)propyl)-1H-indol-5-amine
• 英文别名: 1-[3-(Dimethylamino)propyl]indol-5-amine
• CAS: 1202869-59-7
• 化学式: C₁₃H₁₉N₃
• 分子量: 217.314
• InChiKey: DZPNAKICXUHRED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-(dimethylamino)propyl)-1H-indol-5-amine 在 盐酸 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 0.17h， 生成 N'-[1-[3-(dimethylamino)propyl]indol-5-yl]thiophene-2-carboximidamide;hydrochloride
  参考文献：
  名称：

  1,5-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase inhibitors

  摘要：

  A series of 1,5-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase. A variety of flexible and restricted basic amine side chain substitutions was explored at the 1-position of the indole ring, while keeping the amidine group fixed at the 5-position. Compounds having N-(1-(2-(1-methylpyrrolidin-2-yl) ethyl)- (12, (R)-12, (S)-12 and 13) and N-(1-(1-methylazepan-4-yl)-side chains (14, 15, (-)-15 and (+)-15) showed increased inhibitory activity for the human nNOS isoform and selectivity over eNOS and iNOS isoforms. The most potent compound of the series for human nNOS (IC(50) = 0.02 mu M) (S)-12 showed very good selectivity over the eNOS (eNOS/nNOS = 96-fold) and iNOS (iNOS/nNOS = 850-fold) isoforms. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.022
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium on activated charcoal 、 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.5h， 生成 1-(3-(dimethylamino)propyl)-1H-indol-5-amine
  参考文献：
  名称：

  [EN] FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS
  [FR] INDOLES FONCTIONNALISÉS ET SUBSTITUÉS UTILISÉS EN TANT QU'AGENTS ANTI-CANCÉREUX

  摘要：

  本发明涉及抗肌球蛋白化合物，其制备方法，以及利用本发明的化合物治疗或预防增殖性疾病，优选癌症的方法。

  公开号：

  WO2015074123A1

文献信息

• [EN] FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS<br/>[FR] INDOLES FONCTIONNALISÉS ET SUBSTITUÉS UTILISÉS EN TANT QU'AGENTS ANTI-CANCÉREUX
  申请人：NOVOGEN LTD

  公开号：WO2015074123A1

  公开（公告）日：2015-05-28

  The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a proliferative disease, preferably cancer, using compounds of the invention.

  本发明涉及抗肌球蛋白化合物，其制备方法，以及利用本发明的化合物治疗或预防增殖性疾病，优选癌症的方法。
• AROMATIC AMIDES
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP1178953B1

  公开（公告）日：2003-12-03
• FUNCTIONALISED AND SUBSTITUTED INDOLES AS ANTI-CANCER AGENTS
  申请人：Novogen Ltd.

  公开号：EP3074378A1

  公开（公告）日：2016-10-05
• [EN] AROMATIC AMIDES<br/>[FR] AMIDES AROMATIQUES
  申请人：WARNER LAMBERT CO

  公开号：WO2000068184A1

  公开（公告）日：2000-11-16

  Aromatic and heteroaromatic amides of formula (I) where R?1, R2 and R3¿ can be alkyl, X is alkylene, and R4 is an unsubstituted or substituted aromatic or heteroaromatic group such as naphthyl or fluorenyl, are CNS agents useful for treating pain, depression, anxiety, seizures, and schizophrenia.
• 1,5-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase inhibitors
  作者：Paul Renton、Joanne Speed、Shawn Maddaford、Subhash C. Annedi、Jailall Ramnauth、Suman Rakhit、John Andrews

  DOI：10.1016/j.bmcl.2011.07.022

  日期：2011.9

  A series of 1,5-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase. A variety of flexible and restricted basic amine side chain substitutions was explored at the 1-position of the indole ring, while keeping the amidine group fixed at the 5-position. Compounds having N-(1-(2-(1-methylpyrrolidin-2-yl) ethyl)- (12, (R)-12, (S)-12 and 13) and N-(1-(1-methylazepan-4-yl)-side chains (14, 15, (-)-15 and (+)-15) showed increased inhibitory activity for the human nNOS isoform and selectivity over eNOS and iNOS isoforms. The most potent compound of the series for human nNOS (IC(50) = 0.02 mu M) (S)-12 showed very good selectivity over the eNOS (eNOS/nNOS = 96-fold) and iNOS (iNOS/nNOS = 850-fold) isoforms. (C) 2011 Elsevier Ltd. All rights reserved.