1-(3-chloropropyl)-5-nitro-1H-indole | 187739-84-0

• 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-chloropropyl)-5-nitro-1H-indole
• 英文别名: 1-(3-chloropropyl)-5-nitroindole
• CAS: 187739-84-0
• 化学式: C₁₁H₁₁ClN₂O₂
• 分子量: 238.674
• InChiKey: NQXQRYOSPMPRIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-chloropropyl)-5-nitro-1H-indole 在 palladium on activated charcoal 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 1-(3-(dimethylamino)propyl)-1H-indol-5-amine
  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：

  1-氯-3-碘丙烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到1-(3-chloropropyl)-5-nitro-1H-indole
  参考文献：
  名称：

  1,5 And 3,6- substituted indole compounds having NOS inhibitory activity

  摘要：

  本发明涉及一种一氧化氮合酶（NOS）的抑制剂，特别是那些选择性地抑制神经一氧化氮合酶（nNOS）而不是其他NOS同工酶。本发明的NOS抑制剂，单独或与其他药用活性剂联合使用，可用于治疗或预防诸如中风、再灌注损伤、神经退行性疾病、头部创伤、冠状动脉搭桥手术（CABG）、有或无先兆的偏头痛、伴有触痛的偏头痛、中枢性中风后疼痛（CPSP）、神经病性疼痛或慢性疼痛等病症。

  公开号：

  US20070254940A1

文献信息

• Method of inhibiting neoplastic cells with benzimidazole derivatives
  申请人：——

  公开号：US20030008832A1

  公开（公告）日：2003-01-09

  A method for inhibiting neoplasia, particularly cancerous and precancerous lesions by exposing the affected cells to benzimidazole derivatives.

  一种通过将受影响的细胞暴露于苯并咪唑衍生物来抑制肿瘤，特别是癌症和癌前病变的方法。
• Benzimidazole derivatives
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05998437A1

  公开（公告）日：1999-12-07

  The present invention provides novel benzimidazole derivatives or salts thereof represented by the general formula, ##STR1## wherein R.sup.1 is a hydrogen atom or a halogen atom; R.sup.2 is a phenyl-lower alkyl group; R.sup.3 is a heterocyclic group selected from the group consisting of an indolyl group, indolinyl group, 1H-indazolyl group, 2(1H)-quinolinonyl group, 3,4-dihydro-2(1H)-quinolinonyl group and 1,4-benzoxazinyl group; A is a lower alkylene group; n is 0 or 1. The benzimidazole derivatives or salts of the present invention are effective agents for treating various arteriosclerotic diseases.

  本发明提供了一种新颖的苯并咪唑衍生物或其盐，其通式表示为，其中R.sup.1是氢原子或卤原子；R.sup.2是苯基-低碳基团；R.sup.3是从吲哚基、吲哚啉基、1H-吲哚基、2(1H)-喹啉基、3,4-二氢-2(1H)-喹啉基和1,4-苯并噁唑基中选择的杂环基团；A是低碳基团；n为0或1。本发明的苯并咪唑衍生物或其盐是治疗各种动脉硬化性疾病的有效药物。
• 1,5 and 3,6-substituted indole compounds having NOS inhibitory activity
  申请人：NeurAxon, Inc.

  公开号：US07989447B2

  公开（公告）日：2011-08-02

  The present invention features inhibitors of nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing conditions such as, for example, stroke, reperfusion injury, neurodegeneration, head trauma, CABG, migraine headache with and without aura, migraine with allodynia, central post-stroke pain (CPSP), neuropathic pain, or chronic pain.

  本发明涉及一种一氧化氮合酶（NOS）抑制剂，特别是那些能够选择性地抑制神经型一氧化氮合酶（nNOS）而不影响其他NOS同工酶。本发明的NOS抑制剂可以单独或与其他药物活性剂联合使用，用于治疗或预防中风、再灌注损伤、神经退行性疾病、头部创伤、冠状动脉搭桥术（CABG）、带和不带先兆的偏头痛、带有痛觉过敏的偏头痛、中枢后中风痛（CPSP）、神经性疼痛或慢性疼痛等症状。
• Indolylalkyltriphenylphosphonium Analogues Are Membrane-Depolarizing Mycobactericidal Agents
  作者：Ming Li、Samuel A. Nyantakyi、Pooja Gopal、Dinah binte Aziz、Thomas Dick、Mei-Lin Go

  DOI：10.1021/acsmedchemlett.7b00287

  日期：2017.11.9

  Agents that selectively target the mycobacterial membrane could potentially shorten treatment time for tuberculosis, reduce relapse, and curtail emergence of resistant strains. The lipophilicity and extensive charge-delocalized state of the triphenylphosphonium cation strongly favor accumulation within bacterial membranes. Here, we explored the antimycobacterial activities and membrane-targeting properties of indolylalkyltriphenylphosphonium analogues. The most active analogues preferentially inhibited growth of Mycobacterium tuberculosis H37Rv (MIC50 2-4 mu M) and were bactericidal against Mycobacterium bovis BCG (MBC99 3 mu M). In spite of their propensity to accumulate within membranes, we found no evidence that these compounds permeabilized mycobacterial membranes or induced cell-envelope stress. Our investigations indicated that their bacterical effects stem from sustained depolarization of mycobacterial membranes and ensuing disruptive effects on electron transfer and cell division.
• An efficient conversion of 5-nitroisatin into 5-nitroindole derivative
  作者：Yasuhiro Torisawa、Takao Nishi、Jun-Ichi Minamikawa

  DOI：10.1016/s0960-894x(01)00071-3

  日期：2001.3

  Our process research on OPC-35564 revealed that a mixed borohydride reducing agent (ZrCl4/NaBH4) in DME (Itsuno system) afforded a rapid and direct conversion of N-alkyl-nitroisatin into nitroindole nucleus. Comparison with other reducing agents indicated the superiority of the present system and the key function of ZrCl4. For the manipulation of base-labile isatin, a useful procedure for its N-alkylation using Cu2CO3 is also presented. (C) 2001 Elsevier Science Ltd. All rights reserved.