3-benzyl-1,4-dihydro-4-oxo-2,5,11-trimethyl-6H-pyrido<3,2-b>carbazole | 111249-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-benzyl-1,4-dihydro-4-oxo-2,5,11-trimethyl-6H-pyrido<3,2-b>carbazole
• 英文别名: 3-Benzyl-2,5,11-trimethyl-1,6-dihydropyrido[3,2-b]carbazol-4-one
• CAS: 111249-59-3
• 化学式: C₂₅H₂₂N₂O
• 分子量: 366.462
• InChiKey: QMYGDVUIMMWLBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 溶剂黄146 作用下， 以 二苯醚 、 苯 为溶剂， 反应 3.33h， 生成 3-benzyl-1,4-dihydro-4-oxo-2,5,11-trimethyl-6H-pyrido<3,2-b>carbazole
  参考文献：
  名称：

  In vitro cytotoxicity of carbazole derivatives IV. 5,11-Dimethyl-6H-pyrido[3,2-b]carbazoles substituted on the pyridine ring

  摘要：

  A series of 5,11-dimethyl-6H-pyrido[3,2-b]carbazoles, structurally related to the antitumor drug ellipticine, were synthesized from 3-amino-1,4-dimethyl-9H-carbazole. Among 17 derivatives, bearing various substituents on the pyridine ring, and preliminarily evaluated for cytotoxicity on L1210-cultured cells, 13 (76%) were found to be active. One of them, 5,11-dimethyl-4-ethoxy-6H-pyrido[3,2-b]carbazole, although non-substituted on C-9, displayed an activity similar to that of 9-hydroxy-N-2-methylellipticinium acetate. Structure-activity relationships have been described in detail.

  DOI：

  10.1016/0223-5234(93)90032-a

文献信息

• EFFICIENT SYNTHESIS OF 6H-PYRIDO [3, 2-b] CARBAZOLE DERIVATIVES FROM 3-AMINO-1, 4-DIMETHYL CARBAZOLE
  作者：Jean-Charles Lancelot、Sylvain Rault、Max Robba、Nguyen Huy Dung

  DOI：10.1248/cpb.35.425

  日期：——

  The synthesis of 3-amino-1, 4-dimethylcarbazole is described and its reaction with β-ketoesters gives new 6H-pyrido [3, 2-b] carbazole derivatives.

  介绍了 3-氨基-1，4-二甲基咔唑的合成及其与 β-酮酯的反应，从而得到了新的 6H 吡啶并[3，2-b] 咔唑衍生物。
• Moinet-Hedin V., Tabka T., Gauduchon P., Le Talaer J. Y., Letois B., Lanc+, Eur. J. Med. Chem, 28 (1993) N 9, S 721-726
  作者：Moinet-Hedin V., Tabka T., Gauduchon P., Le Talaer J. Y., Letois B., Lanc+

  DOI：——

  日期：——
• LANCELOT J. -CH.; RAULT S.; ROBBA M.; DUNG NGUYEN HUY, CHEM. AND PHARM. BULL., 35,(1987) N 1, 425-428
  作者：LANCELOT J. -CH.、 RAULT S.、 ROBBA M.、 DUNG NGUYEN HUY

  DOI：——

  日期：——
• In vitro cytotoxicity of carbazole derivatives IV. 5,11-Dimethyl-6H-pyrido[3,2-b]carbazoles substituted on the pyridine ring
  作者：V Moinet-Hedin、T Tabka、P Gauduchon、JY Le Talaer、B Letois、JC Lancelot、S Rault、M Robba

  DOI：10.1016/0223-5234(93)90032-a

  日期：1993.1

  A series of 5,11-dimethyl-6H-pyrido[3,2-b]carbazoles, structurally related to the antitumor drug ellipticine, were synthesized from 3-amino-1,4-dimethyl-9H-carbazole. Among 17 derivatives, bearing various substituents on the pyridine ring, and preliminarily evaluated for cytotoxicity on L1210-cultured cells, 13 (76%) were found to be active. One of them, 5,11-dimethyl-4-ethoxy-6H-pyrido[3,2-b]carbazole, although non-substituted on C-9, displayed an activity similar to that of 9-hydroxy-N-2-methylellipticinium acetate. Structure-activity relationships have been described in detail.