5-(5-Phenyl-pentyl)-10H-indolo[3,2-b]quinolin-5-ium; bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(5-Phenyl-pentyl)-10H-indolo[3,2-b]quinolin-5-ium; bromide
• 英文别名: 5-(5-phenylpentyl)-10H-indolo[3,2-b]quinolin-5-ium;bromide
• 化学式: Br*C₂₆H₂₅N₂
• 分子量: 445.402
• InChiKey: BBKWEIKKCMIKQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  19.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  10H-吲哚并[3,2-b]喹啉 、 (5-溴正戊基)苯 以 环丁砜 为溶剂， 生成 5-(5-Phenyl-pentyl)-10H-indolo[3,2-b]quinolin-5-ium; bromide
  参考文献：
  名称：

  Substituted Indoloquinolines as New Antifungal Agents

  摘要：

  Cryptolepine (2) possesses desirable properties to serve as a lead in developing new antifungal agents. Using SAR techniques, several analogues of cryptolepine were designed to increase potency and to broaden the antifungal spectrum over several opportunistic microorganisms. A number of 2-substituted indoloquinolines have been synthesized and evaluated in antifungal screens and several have been shown to increase potency and expand the antifungal spectrum of cryptolepine. Comparison of MICs of a number of these analogues with standard antifungal agents, shows them to be comparable to Amphotericin B and Ketoconazole. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00401-1

文献信息

• Probing the N-5 Region of the Indoloquinoline Alkaloid, Cryptolepine for Anticryptococcal Activity
  作者：Seth Y Ablordeppey、Pingchen Fan、Alice M Clark、Alison Nimrod

  DOI：10.1016/s0968-0896(98)00244-2

  日期：1999.2

  N-5 Alkylated analogues of cryptolepine were synthesized and tested for anticryptococcal activity. Evidence provided in this study suggests that the active form of cryptolepine consists of the flat tetracyclic aromatic ring with the methyl group on the N-5 atom. It was also found that changes in the electronic density around the N-5 atom do not appear to affect activity. Steric hindrance of the N-5 substituents seems to decrease activity. Through systematic modification of the N-5 alkyl groups, omega-phenylpentyl group was shown to possess the highest potency thus far. (C) 1999 Elsevier Science Ltd. All rights reserved.