6-benzyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole | 74606-36-3

• 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: 6-benzyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
• 英文别名: 6-benzyl-5,11-dimethylpyrido[4,3-b]carbazole
• CAS: 74606-36-3
• 化学式: C₂₄H₂₀N₂
• 分子量: 336.436
• InChiKey: NBZZGVUGOCNNNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  6-benzyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以75%的产率得到椭圆玫瑰树碱
  参考文献：
  名称：

  Friedel-Crafts 环脱水法合成玫瑰树碱和 9-甲氧基玫瑰树碱

  摘要：

  报告了生物学上重要的吡啶并 [4,3-b] 咔唑生物碱、玫瑰树碱和 9-甲氧基玫瑰树碱的权宜之计合成。我们的合成方法应用关键的 H3PO4 介导的 Friedel-Crafts 环脱水来构建吡啶核心。

  DOI：

  10.1055/s-0034-1379305
• 作为产物：
  描述：

  3,4-dihydro-4-methylcarbazol-1(2H)-one 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 sodium carbonate 、 一水合肼 、 三氯氧磷 、 三乙二醇 作用下， 以 1,4-二氧六环 为溶剂， 反应 29.0h， 生成 6-benzyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
  参考文献：
  名称：

  Yokoyama, Yuusaku; Okuyama, Naomi; Iwadate, Shinji, Journal of the Chemical Society. Perkin transactions I, 1990, # 5, p. 1319 - 1329

  摘要：

  DOI：

文献信息

• Synthesis of potential antineoplastic agents. XXVII. (Reissert compound studies. XLIV.). The ellipticine reissert compound as an intermediate in the syntheses of ellipticine analogs
  作者：Frank D. Popp、Seshadri Veeraraghavan

  DOI：10.1002/jhet.5570190603

  日期：1982.11

  were converted to Reissert compounds. Alkylation of the 6-benzylellipticine Reissert compound gave a series of 1-substituted-6-benzylellipticines. 1-Cyanoellipticine, obtained through the Reissert compound, was hydrolyzed to ellipticine-1-carboxamide hydrochloride which was active against P388 lymphocytic leukemia. Other aspects of the chemistry of the ellipticine Reissert compound are presented.

  玫瑰树碱和许多玫瑰树碱类似物被转化为Reissert化合物。6-苄基玫瑰树碱Reissert化合物的烷基化反应产生了一系列1-取代的6-苄基玫瑰树碱。通过Reissert化合物获得的1-氰基玫瑰树碱被水解为玫瑰树碱1-羧酰胺盐酸盐，该盐对P388淋巴细胞性白血病具有活性。玫瑰树碱Reissert化合物的化学反应的其他方面也有所介绍。
• Tandem directed metalation reactions. Short syntheses of polycyclic aromatic hydrocarbons and ellipticine alkaloids
  作者：M. Watanabe、V. Snieckus

  DOI：10.1021/ja00524a059

  日期：1980.2
• Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole.
  作者：Adrian T. Boogaard、Upendra K. Pandit、Gerrit-Jan Koomen

  DOI：10.1016/s0040-4020(01)85018-3

  日期：1994.4

  The N-oxide of ellipticine can be used for the introduction of a chlorine atom at carbon-3 of the ellipticine nucleus. According to modelstudies with 5,8-dimethylisoquinoline-N-oxide the reaction is guided both by steric hindrance and by nitrogen-6 of the ellipticine system. Attempted nucleophilic substitution reactions of 3-chloro-ellipticines failed. The high cytostatic activity observed for 9-acetylellipticine stimulated us to prepare the corresponding deaza analogue. This compound was synthesized in 2 steps starting from 1-methylindole. Regioselective acetylation at C-2 was accomplished using acetic anhydride and ZnCl2 as a catalyst. Under a variety of other conditions the 2,9-diacetylproduct was formed and no 9-monoacetylated compound could be isolated. Just as the parent compound, the acetylated deazaellipticines showed only very low cytostatic activity.
• Reaction of 1-Benzylindole-2,3-dicarboxylic Anhydride with 3-Bromo-4-lithiopyridine: Formal Synthesis of Ellipticine
  作者：Yasuyoshi Miki、Yoshitaka Tada、Ko-ichi Matsushita

  DOI：10.3987/com-98-8192

  日期：——

  Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with 3-bromo-4-lithiopyridine gave 2-(3-bromoisonicotinoyl)indole-3-carboxylic acid as the sole product. The indole-3-carboxylic acid could be converted to 6-benzylellipticine quinone in five steps.
• Reissert Compound Studies; XXXIII. The Synthesis of Ellipticine and Quinine Reissert Compounds
  作者：Seshadri Veeraraghavan、Frank D. Popp

  DOI：10.1055/s-1980-29028

  日期：——