6-cyano-5-hydroxy-12-methylindolo[2,3-a]carbazole | 241474-88-4

• 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
• 英文名称: 6-cyano-5-hydroxy-12-methylindolo[2,3-a]carbazole
• 英文别名: 5-hydroxy-12-methyl-11H-indolo[2,3-a]carbazole-6-carbonitrile
• CAS: 241474-88-4
• 化学式: C₂₀H₁₃N₃O
• 分子量: 311.343
• InChiKey: NOUAWDWDINGQBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 6-cyano-5-hydroxy-12-methylindolo[2,3-a]carbazole 以 乙醚 为溶剂， 反应 0.5h， 以97%的产率得到6-氰基-5-甲氧基-12-甲基吲哚并(2,3-a)咔唑
  参考文献：
  名称：

  组合定向正交和远程金属化交叉耦合策略。苯并[a]咔唑的通用方法和未命名的吲哚[2,3-a]咔唑生物碱的合成。

  摘要：

  [反应：见正文]已证明了通过金属化-交叉偶联序列生产苯并[a]咔唑的有效途径，并将其应用于合成抗肿瘤和抗病毒生物碱6-氰基-5-甲氧基-12-甲基吲哚[已经实现了2，3-a]咔唑。

  DOI：

  10.1021/ol049780x
• 作为产物：
  描述：

  o-草酰甲苯胺 在 对甲苯磺酰叠氮 、 potassium tert-butylate 、 乙酸酐 、 三乙胺 、 potassium hydroxide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 6-cyano-5-hydroxy-12-methylindolo[2,3-a]carbazole
  参考文献：
  名称：

  通过光诱导的卡宾介导的C–H插入反应 合成苯并[ a ]咔唑和吲哚[2,3- a ]咔唑†

  摘要：

  通过将光致分子内2-芳基-3-（α-重氮羰基）吲哚插入C-H分子内，已完成了5-羟基-苯并[ a ]咔唑的新合成。该方法适用于天然产物6-氰基-5-甲氧基-吲哚并[2，3- a ]咔唑8和11及其衍生物的合成。

  DOI：

  10.1039/c4ra00442f

文献信息

• Natural product leads for drug discovery: Isolation, synthesis and biological evaluation of 6-cyano-5-methoxyindolo[2,3-a]carbazole based ligands as antibacterial agents
  作者：Songpo Guo、Suresh K. Tipparaju、Scott D. Pegan、Baojie Wan、Shunyan Mo、Jimmy Orjala、Andrew D. Mesecar、Scott G. Franzblau、Alan P. Kozikowski

  DOI：10.1016/j.bmc.2009.08.061

  日期：2009.10

  Indolo[2,3-a]carbazole based inhibitors were synthesized from readily available indigo via a seven-step linear synthetic sequence with a moderate overall yield. The inhibitors were selectively and readily functionalized at the nitrogen on the indole portion of the carbazole unit. The synthesized analogs displayed moderate inhibitory activities toward Bacillus anthracis and Mycobacterium tuberculosis

  Indolo[2,3- a ]咔唑类抑制剂是从容易获得的靛蓝中通过七步线性合成序列以中等总产率合成的。抑制剂在咔唑单元的吲哚部分上的氮上被选择性且容易地官能化。合成的类似物对炭疽芽孢杆菌和结核分枝杆菌显示出中等抑制活性，表明吲哚[2,3- a ]咔唑可作为开发新药对抗炭疽和结核病感染的有希望的线索。
• Synthetic Study Directed toward Derivatives of Biologically Active Indolo[2,3-a]carbazole
  作者：Masanori Somei、Masako Sato、Yoshiaki Suzuki、Fumio Yamada

  DOI：10.3987/com-09-s(s)79

  日期：——

  Various derivatives of (6R*,6aR*)-6-chloro-6a-hydroxy-5,6,6a,12-tetrahydroindolo[2,3-a]carbazole-5-one (8) and 6-cyano-5-hydroxyindolo[2,3-a]carbazole (9) are prepared. Preparations of (6R*,6aR*,11aR*)-6-chloro-11a-cyano-6a-hydroxy- (11) and 12-substituted 6-(Z)-aminomethylidene-5,6,6a,11,11a,12-hexahydroindolo[2,3-a]carbazole-5-ones (15) are also reported.
• Short Step Synthesis of an Antibiotic, 6-Cyano-5-methoxy-12-methylindolo[2,3-a]carbazole
  作者：Masanori Somei、Fumio Yamada、Yoshiaki Suzuki、Shinobu Ohmoto、Hiroyuki Hayashi

  DOI：10.3987/com-04-s(p)29

  日期：——

  For evaluating the effectiveness of organic synthesis, both intellectual property factor (IPF) and application potential factor (APF) are proposed. As a representative example, a highly effective synthetic method with IPF value of 53.8 and APF value of 100 has been established starting from indigo directing toward an antibiotic, 6-cyano-5-methoxy-12-methylindolo[2,3-a]carbazole, using only conventional reagents without using any protecting groups.
• Short Step Syntheses of a Natural Product, 6-Cyano-5-methoxy-12-methylindolo[2,3-a]carbazole and Novel 6-Aminoindolo[2,3-a]thiazolo[5,4-c]carbazoles
  作者：Masanori Somei、Hiroyuki Hayashi、Yoshiaki Suzuki

  DOI：10.3987/com-99-8531

  日期：——
• Combined Directed <i>Ortho</i> and Remote Metalation−Cross-Coupling Strategies. General Method for Benzo[<i>a</i>]carbazoles and the Synthesis of an Unnamed Indolo[2,3-<i>a</i>]carbazole Alkaloid
  作者：Xiongwei Cai、Victor Snieckus

  DOI：10.1021/ol049780x

  日期：2004.7.1

  [reaction: see text] An efficient route to benzo[a]carbazoles via a metalation-cross-coupling sequence has been demonstrated and its application to the synthesis of the antitumor and antiviral alkaloid 6-cyano-5-methoxy-12-methylindolo[2,3-a]carbazole has been achieved.

  [反应：见正文]已证明了通过金属化-交叉偶联序列生产苯并[a]咔唑的有效途径，并将其应用于合成抗肿瘤和抗病毒生物碱6-氰基-5-甲氧基-12-甲基吲哚[已经实现了2，3-a]咔唑。