1-methyl-9H-pyrido[4,3-b]indole

• 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-methyl-9H-pyrido[4,3-b]indole
• 英文别名: 4-methyl-5H-pyrido[4,3-b]indole；SK4M
• 化学式: C₁₂H₁₀N₂
• mdl: MFCD18803707
• 分子量: 182.225
• InChiKey: VGHYDGMSJXYFDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  碳酸二甲酯 、 1-methyl-9H-pyrido[4,3-b]indole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4,5-dimethyl-5H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Polymethylated γ-Carbolines with Potent Anti-Bovine Viral Diarrhea Virus (BVDV) Activity

  摘要：

  Several anti-BVDV agents with a polymethylated gamma-carboline skeleton were synthesized, and their anti-BVDV activity was evaluated. The most potent antiviral agent, SK3M4M5M (20), was synthesized by Pd-catalyzed Buchwald-Hartwig amination reaction followed by annulation reaction as key steps. The structure-activity relationship was analyzed.

  DOI：

  10.3987/com-08-s(f)68
• 作为产物：
  描述：

  α-<1-(Phenylsulfonyl)-2-indolyl>α,α-dimethylmethanol 在 盐酸羟胺 、 四丁基氟化铵 、 sodium acetate 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 27.5h， 生成 1-methyl-9H-pyrido[4,3-b]indole
  参考文献：
  名称：

  生物活性γ-咔啉衍生物的有效合成途径

  摘要：

  摘要 为合成抗牛病毒性腹泻病毒药物，即 4-甲基-γ-咔啉 (SK4M) 1, 3-甲基-γ-咔啉 (SK3M) 2, 5-甲基-γ，建立了一条高效、快捷的合成路线。 -咔啉（SK5M）3，以及一种新的γ-咔啉衍生物4，以热电环化反应为关键步骤。化合物 4 对人宫颈癌细胞系 HeLa 和白血病细胞系 HL-60 的细胞毒性评价提供的 CC50 值分别为 19.5 和 18.8 µM。图形概要

  DOI：

  10.1080/00397911.2015.1103874

文献信息

• 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.
• A New Deprotection Procedure for the N-Methoxymethyl Group of N-Methoxymethyl-heterocyclic Compounds
  作者：Satoshi Hibino、Takeshi Kuwada、Miyako Fukui、Maho Hirayama、Junko Nobuhiro、Tominari Choshi

  DOI：10.3987/com-02-s(m)26

  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.
• Efficient synthetic route toward biologically active γ-carboline derivatives
  作者：Dattatray G. Hingane、Nikita P. Parekh、Ayesha Khan、Radhika S. Kusurkar

  DOI：10.1080/00397911.2015.1103874

  日期：2016.1.17

  ABSTRACT An efficient and short route was established for the synthesis of anti-bovine viral diarrhea virus agents, namely 4-methyl-γ-carboline (SK4M) 1, 3-methyl-γ-carboline (SK3M) 2, 5-methyl-γ-carboline (SK5M) 3, and a new γ-carboline derivative 4, using thermal electrocyclization reaction as a key step. The evaluation of cytotoxicity of compound 4 against human cervical cancer cell line HeLa and

  摘要 为合成抗牛病毒性腹泻病毒药物，即 4-甲基-γ-咔啉 (SK4M) 1, 3-甲基-γ-咔啉 (SK3M) 2, 5-甲基-γ，建立了一条高效、快捷的合成路线。 -咔啉（SK5M）3，以及一种新的γ-咔啉衍生物4，以热电环化反应为关键步骤。化合物 4 对人宫颈癌细胞系 HeLa 和白血病细胞系 HL-60 的细胞毒性评价提供的 CC50 值分别为 19.5 和 18.8 µM。图形概要
• Polymethylated γ-Carbolines with Potent Anti-Bovine Viral Diarrhea Virus (BVDV) Activity
  作者：Hiroshi Aoyama、Kumiko Sako、Shinichi Sato、Masahiko Nakamura、Hiroyuki Miyachi、Yukinori Goto、Mika Okamoto、Masanori Baba、Yuichi Hashimoto

  DOI：10.3987/com-08-s(f)68

  日期：——

  Several anti-BVDV agents with a polymethylated gamma-carboline skeleton were synthesized, and their anti-BVDV activity was evaluated. The most potent antiviral agent, SK3M4M5M (20), was synthesized by Pd-catalyzed Buchwald-Hartwig amination reaction followed by annulation reaction as key steps. The structure-activity relationship was analyzed.