3-甲基-5H-吡啶并[4,3-b]吲哚 | 58096-07-4

• 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
• 中文名称: 3-甲基-5H-吡啶并[4,3-b]吲哚
• 英文名称: 3-methyl-5H-pyrido<4,3-b>indole
• 英文别名: SK3M；3-methyl-5H-pyrido[4,3-b]indole；2-Methyl-(9H)-pyrido<4,3-b>indol
• CAS: 58096-07-4
• 化学式: C₁₂H₁₀N₂
• mdl: MFCD04113950
• 分子量: 182.225
• InChiKey: MNWHCHUSCPJCHV-UHFFFAOYSA-N

物化性质

• 熔点：
  225-228 °C(Solv: benzene (71-43-2))
• 沸点：
  386.9±22.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)
• 溶解度：
  >27.3 [ug/mL]

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 、 3-甲基-5H-吡啶并[4,3-b]吲哚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 SK3M5M
  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：

  4-氯-2-甲基吡啶 在 焦磷酸 作用下， 反应 0.5h， 生成 3-甲基-5H-吡啶并[4,3-b]吲哚
  参考文献：
  名称：

  Synthesis and DNA Binding Properties of γ-Carbolinium Derivatives and Benzologues

  摘要：

  The 5H-pyrido[4,3-b]indole, 11H-indolo[3,2-c]quinoline, 5H-benzo[f]pyrido[4,3-b]indole, and 13H-benz[5,6]indolo[3,2-c]quinoline heteroaromatic nuclei have been synthesized by the Graebe-Ullmann method by classical heating or under microwave irradiation. These tri-, tetra-, and pentacyclic compounds were transformed into the corresponding cationic derivatives by N-alkylation, and the DNA-binding properties of the resulting cationic systems were examined using UV-vis spectroscopy, viscometric determinations, and molecular modeling techniques. The tetracyclic cations were transformed into his-salts by means of a diethyl bispiperidine rigid chain and a more flexible polyamide linker, but the low solubility of these bis-salts made the study of their bisintercalating properties difficult.

  DOI：

  10.1021/jo960266h

文献信息

• 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
• [EN] BET BROMODOMAIN INHIBITORS AND THERAPEUTIC METHODS USING THE SAME<br/>[FR] INHIBITEURS DE BROMODOMAINES BET ET MÉTHODES THÉRAPEUTIQUES LES UTILISANT
  申请人：UNIV MICHIGAN

  公开号：WO2014164596A1

  公开（公告）日：2014-10-09

  Inhibitors of BET bromodomains and compositions containing the same are disclosed. Methods of using the BET bromodomain inhibitors in the treatment of diseases and conditions wherein inhibition of BET bromodomain provides a benefit, like cancers, also are disclosed.

  本文披露了BET bromodomain抑制剂及含有它们的组合物。还披露了使用BET bromodomain抑制剂治疗疾病和状况的方法，其中BET bromodomain的抑制提供益处，如癌症等疾病。
• BET bromodomain inhibitors and therapeutic methods using the same
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US10391175B2

  公开（公告）日：2019-08-27

  Inhibitors of BET bromodomains and compositions containing the same are disclosed. Methods of using the BET bromodomain inhibitors in the treatment of diseases and conditions wherein inhibition of BET bromodomain provides a benefit, like cancers, also are disclosed.

  本研究公开了 BET 溴基链抑制剂和含有这些抑制剂的组合物。此外，还公开了将 BET 溴基链抑制剂用于治疗 BET 溴基链抑制可带来益处的疾病和病症（如癌症）的方法。
• 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.
• DUCROSQ C.; CIVIER A.; ANDRE LOUISFERT J.; BISAGNI E., J. HETEROCYCL. CHEM. <JHTC-AD>, 1975, 12, NO 5, 963-967
  作者：DUCROSQ C.、 CIVIER A.、 ANDRE LOUISFERT J.、 BISAGNI E.

  DOI：——

  日期：——