3-methyl-γ-carboline | 115191-20-3

• 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: 3-methyl-γ-carboline
• 英文别名: 2-Methylpyrido[4,3-b]indole
• CAS: 115191-20-3
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: QCKPPJYQWXOQMU-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  291.6±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-γ-carboline 在 sodium tetrahydroborate 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 27.5h， 生成 甲苯咔啉
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1010455819181
• 作为产物：
  描述：

  1-phenyl-1H-[1,2,3]triazolo[4,5-c]pyridine 在 氢氧化钾 、 paraffin 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.67h， 生成 3-methyl-γ-carboline
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1014003010986

文献信息

• Characterizations of cationic γ-carbolines binding with double-stranded DNA by spectroscopic methods and AFM imaging
  作者：Tao Jia、Jing Wang、Peng Guo、Junping Yu

  DOI：10.1039/c4ob01905a

  日期：——

  Because of differences in their structures, cationic γ-carbolines intercalate into DNA with different activities.

  由于它们结构的差异，阳离子γ-咔唑以不同的活性插入到DNA中。
• γ-Carboline derivatives with anti-bovine viral diarrhea virus (BVDV) activity
  作者：Kumiko Sako、Hiroshi Aoyama、Shinichi Sato、Yuichi Hashimoto、Masanori Baba

  DOI：10.1016/j.bmc.2008.01.052

  日期：2008.4.1

  Based on anti-viral screening of our heteroaromatics derived from thalidomide, the gamma-carboline skeleton has been identified as a superior scaffold structure for compounds with potent anti-bovine viral diarrhea virus (BVDV) activity. Structural development studies led to a potent anti-viral agent, SK5M (5-methyl-gamma-carboline), with the EC50 of 0.26 mu M. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• Robinson; Thornley, Journal of the Chemical Society, 1924, vol. 125, p. 2174
  作者：Robinson、Thornley

  DOI：——

  日期：——
• ANTI-VIRAL AGENT CONTAINING HETEROCYCLIC AROMATIC COMPOUND AS ACTIVE INGREDIENT
  申请人：Baba Masanori

  公开号：US20100256379A1

  公开（公告）日：2010-10-07

  The present invention relates to an anti-viral agent comprising a compound represented by the following formula (I): (wherein X represents CH, a nitrogen atom, an oxygen atom, or a sulfur atom; Y and Z are the same or different and each represents a nitrogen atom or C—R 8 , and at least one of them represents a nitrogen atom; R 1 to R 8 are the same or different and each represents a hydrogen atom, a linear C 1-10 -hydrocarbon group, a hydroxy group, or a substituted or unsubstituted benzyl group; and, when X represents an oxygen atom or a sulfur atom, R 5 is absent), or the following formula (II): (wherein X′ represents CH or a nitrogen atom; Y′ and Z′ are the same or different and each represents a nitrogen atom or N—R 9 , or C—R 8 and at least one of them represents a nitrogen atom or N—R 9 ; R 1 to R 4 and R 6 to R 8 are as defined above; R 9 represents a hydrogen atom, a linear C 1-10 -hydrocarbon group, a hydroxy group, or a substituted or unsubstituted benzyl group; and, the C ring has the maximum number of double bonds at the dotted line portion) or a pharmaceutically acceptable salt thereof.