8,9,10,11-tetrahydro-7H-pyrido[3,2-a]carbazole | 163042-58-8

• 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: 8,9,10,11-tetrahydro-7H-pyrido[3,2-a]carbazole
• 英文别名: 8,9,10,11-tetrahydro-7H-pyrido[3,2-a]carbazole；8,9,10,11-Tetrahydro-7H-pyrido[3,2-a]carbazol
• CAS: 163042-58-8
• 化学式: C₁₅H₁₄N₂
• 分子量: 222.29
• InChiKey: LOLMDEBWQFGHOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  8,9,10,11-tetrahydro-7H-pyrido[3,2-a]carbazole 在 四氯苯醌 、 xylene 作用下， 生成 11H-pyrido[3,2-a]carbazole
  参考文献：
  名称：

  吡啶并咔唑的合成

  摘要：

  7H-吡啶并(2,3-c)- (IX, R=H) 和 7H-吡啶并(3,2-c)咔唑 (V, R=H) 已通过明确的路线合成，并显示与由 Fischer-吲哚闭环产生的产物，然后分别将环己酮的 6-和 7-喹啉腙脱氢。环己酮的 N-取代-1,2,3,4-四氢-6-和-7-喹啉腙环化，然后水解和脱氢产生线性多环系统，6H-吡啶并（3,2-b）-（ VIII) 和 10H-吡啶并(2,3-b)咔唑 (IV)。现在已经制备了12种可能的吡啶并咔唑。1-苯基-5-氨基-1-苯并-三唑(X)的Skraup反应产物的结构已经确定。

  DOI：

  10.1139/v52-084
• 作为产物：
  描述：

  喹啉-5-硼酸 在 盐酸 、 copper(II) acetate monohydrate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 19.0h， 生成 8,9,10,11-tetrahydro-7H-pyrido[3,2-a]carbazole
  参考文献：
  名称：

  铜酸直接催化从硼酸合成吡咯并稠合的杂环

  摘要：

  提出了从硼酸，DBAD（二叔丁基重氮二羧酸二叔丁酯）和可烯化的醛和酮制备氮杂吲哚和相关的吡咯并稠合杂环的简便方法。反应通过一锅四步的级联序列进行，关键步骤包括铜催化的硼酸与DBAD的偶联和费歇尔吲哚化作用，从而可利用各种药学上感兴趣的杂环，包括吡咯并吡啶，-嘧啶，-喹啉，易得的氮杂-芳基硼酸前体中的-和-异喹啉。

  DOI：

  10.1016/j.tetlet.2011.11.091

文献信息

• Ferlin; Chiarelotto; Marzano, Il Farmaco, 1995, vol. 50, # 2, p. 91 - 98
  作者：Ferlin、Chiarelotto、Marzano、Mobilio、Carlassare、Baccichetti

  DOI：——

  日期：——
• Huisgen, Justus Liebigs Annalen der Chemie, 1948, vol. 559, p. 101,142
  作者：Huisgen

  DOI：——

  日期：——
• Clemo; Felton, Journal of the Chemical Society, 1951, p. 672,673
  作者：Clemo、Felton

  DOI：——

  日期：——
• 167. Attempts to find new antimalarials. Part XXI
  作者：M. J. S. Dewar

  DOI：10.1039/jr9440000615

  日期：——
• Synthesis and biological properties of a new series of N-pyrido substituted tetrahydrocarbazoles
  作者：M.G. Ferlin、G. Chiarelotto、C. Marzano、E. Severin、F. Baccichetti、F. Carlassare、M. Simonato、F. Bordin

  DOI：10.1016/s0014-827x(98)00048-2

  日期：1998.6

  A series of methyl and ethyl quaternary pyridiniumtetrahydrocarbazoles was synthesized and studied in comparison with ellipticine, chosen as a reference. In general, their antiproliferative activity, tested in different biological substrates, appeared to be higher than that of the corresponding non-quaternarized compounds. This fact could be attributed to the introduction of a positive charge in the molecule, which can stabilize the molecular complex they form with DNA. In a prokaryotic system, the T2 bacteriophage, both quaternarized and non-quaternarized compounds inhibited its infectivity moderately, in a similar way to ellipticine. This effect seemed to be connected to a direct activity on the virions rather than on the indicator bacteria. In mammalian cells, the pyridiniumtetrahydrocarbazoles were more effective. In particular, they appeared to be very active in inhibiting DNA synthesis in Ehrlich ascites cells; some of them were as effective as ellipticine. However, pyridiniumtetrahydrocarbazoles were less active in comparison with ellipticine when their capacity for inhibiting the clonal growth in Chinese hamster ovary (CHO) cells was tested. A similar picture was obtained studying the formation of chromosome aberrations and of sister chromatid exchanges in the same cells. These different responses can be explained considering that the data on DNA synthesis reflect effects only on DNA replication within a short time, without considering any later consequences; on the contrary, in the long-term tests, other events, which lead to cell killing or genotoxicity, can take place. Pyridiniumtetrahydrocarbazoles damage DNA, inducing double-strand breaks efficiently. These observations, together with the data already obtained on unsubstituted derivatives, suggest the pyridiniumtetrahydrocarbazoles induce antiproliferative and genotoxic effects, very probably by inhibiting topoisomerase II. (C) 1998 Elsevier Science S.A. All rights reserved.