6-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium iodide | 1195996-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 6-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium iodide
• 英文别名: 6-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium;iodide
• CAS: 1195996-55-4
• 化学式: C₈H₉N₂*I
• 分子量: 260.077
• InChiKey: JUIICGOBLLBOTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  135-138 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.0
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  6-氮杂吲哚 、 碘甲烷 以 甲苯 为溶剂， 反应 6.0h， 以60%的产率得到6-methyl-1H-pyrrolo[2,3-c]pyridin-6-ium iodide
  参考文献：
  名称：

  Structure–activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues

  摘要：

  Based on the indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3) and isoneocryptolepine (4), used as lead compounds for new antimalarial agents, a series of tricyclic and bicyclic analogues, including carbolines, azaindoles, pyrroloquinolines and pyrroloisoquinolines was synthesized and biologically evaluated. None of the bicyclic compounds was significantly active against the chloroquine-resistant strain Plasmodium falciparum K1, in contrast to the tricyclic derivatives. The tricyclic compound 2-methyl-2H-pyrido[3,4-b] indole (9), or 2-methyl-beta-carboline, showed the best in vitro activity, with an IC50 value of 0.45 mu M against P. falciparum K1, without apparent cytotoxicity against L6 cells (SI > 1000). However, this compound was not active in the Plasmodium berghei mouse model. Structure-activity relationships are discussed and compared with related naturally occurring compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.057

文献信息

• Structure–activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues
  作者：Gitte Van Baelen、Steven Hostyn、Liene Dhooghe、Pál Tapolcsányi、Péter Mátyus、Guy Lemière、Roger Dommisse、Marcel Kaiser、Reto Brun、Paul Cos、Louis Maes、György Hajós、Zsuzsanna Riedl、Ildikó Nagy、Bert U.W. Maes、Luc Pieters

  DOI：10.1016/j.bmc.2009.08.057

  日期：2009.10

  Based on the indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3) and isoneocryptolepine (4), used as lead compounds for new antimalarial agents, a series of tricyclic and bicyclic analogues, including carbolines, azaindoles, pyrroloquinolines and pyrroloisoquinolines was synthesized and biologically evaluated. None of the bicyclic compounds was significantly active against the chloroquine-resistant strain Plasmodium falciparum K1, in contrast to the tricyclic derivatives. The tricyclic compound 2-methyl-2H-pyrido[3,4-b] indole (9), or 2-methyl-beta-carboline, showed the best in vitro activity, with an IC50 value of 0.45 mu M against P. falciparum K1, without apparent cytotoxicity against L6 cells (SI > 1000). However, this compound was not active in the Plasmodium berghei mouse model. Structure-activity relationships are discussed and compared with related naturally occurring compounds. (C) 2009 Elsevier Ltd. All rights reserved.