2,5,11-三甲基-1,6-二氢吡啶并[3,2-b]咔唑-4-酮 | 111249-53-7

• 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
• 中文名称: 2,5,11-三甲基-1,6-二氢吡啶并[3,2-b]咔唑-4-酮
• 英文名称: 1,4-dihydro-4-oxo-2,5,11-trimethyl-6H-pyrido<3,2-b>carbazole
• 英文别名: 1,4-Dihydro-4-oxo-2,5,11-trimethyl-6H-pyrido(3,2-b)carbazole；2,5,11-trimethyl-1,6-dihydropyrido[3,2-b]carbazol-4-one
• CAS: 111249-53-7
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: VVJBLODMXAQPND-UHFFFAOYSA-N

物化性质

• 熔点：
  265 °C
• 沸点：
  516.0±50.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5,11-三甲基-1,6-二氢吡啶并[3,2-b]咔唑-4-酮 、 乙酸酐 生成 4-acetoxy-2,5,11-trimethyl-6H-pyrido<3,2-b>carbazole
  参考文献：
  名称：

  EFFICIENT SYNTHESIS OF 6H-PYRIDO [3, 2-b] CARBAZOLE DERIVATIVES FROM 3-AMINO-1, 4-DIMETHYL CARBAZOLE

  摘要：

  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。

  DOI：

  10.1248/cpb.35.425
• 作为产物：
  描述：

  3-amino-1,4-dimethyl-9H-carbazole 在 溶剂黄146 作用下， 以 二苯醚 、 苯 为溶剂， 反应 3.33h， 生成 2,5,11-三甲基-1,6-二氢吡啶并[3,2-b]咔唑-4-酮
  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

• Structure study on antitumor ellipticine homologue, 1,4-dihydro-4-oxo-2,5,11-trimethyl-6H-pyrido (3,2-b) carbazole by X-ray diffraction.
  作者：BERNARD VIOSSAT、NGUYEN-HUY DUNG、JEAN-CHARLES LANCELOT、SIMONE BENAZETH、SYLVAIN RAULT、MAX ROBBA

  DOI：10.1248/cpb.35.1724

  日期：——

  The synthesis of 1, 4-dihydro-4-oxo-2, 5, 11-trimethy1-6H-pyrido [3, 2-2b] carbazole was described and the lactam-lactim tauromerism was discussed. C18H16N2O crystallizes in space group P21/c with Dm=1.30 (2) Mg·m-3 in acetonitrile with a=16.179 (4), b=14.900 (3). c=12.702 (3) Å, β=112.28 (2), V=2833.6 Å3, Z=8. The crystalstructure was investigated by X-ray diffraction method with final R=0.04 for 2355 independent reflections. In the two molecules, the lactam form was observed while the lactim for was found with many derivatives as well in solid state as in solution. The carbazole ring is planar while the 1, 4- dihydro-4-oxo-pyridine deviates from planarity. The molecules have rather small overlapping and the molecular packing involves many hydrogen bonds.

  介绍了 1，4-二氢-4-氧代-2，5，11-三甲基 1-6H-吡啶并[3，2-2b]咔唑的合成，并讨论了内酰胺-内酰胺的牛磺酰构。C18H16N2O 在空间群 P21/c 中结晶，乙腈中 Dm=1.30 (2) Mg-m-3，a=16.179 (4)，b=14.900 (3)，c=12.702 (3) Å，β=112.28 (2)，V=2833.6 Å3，Z=8。晶体结构采用 X 射线衍射法进行研究，2355 个独立反射的最终 R=0.04 。在这两种分子中，观察到了内酰胺形式，而在固态和溶液中发现了许多衍生物的内酰胺形式。咔唑环是平面的，而 1，4-二氢-4-氧代吡啶则偏离平面。这些分子的重叠度相当小，分子排列涉及许多氢键。
• 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：——