7-Methyl-4-oxo-3,6-diphenyl-pyrrolo[2,1-d][1,2,3,5]tetrazine-8-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-Methyl-4-oxo-3,6-diphenyl-pyrrolo[2,1-d][1,2,3,5]tetrazine-8-carbonitrile
• 英文别名: 7-methyl-4-oxo-3,6-diphenylpyrrolo[2,1-d][1,2,3,5]tetrazine-8-carbonitrile
• 化学式: C₁₉H₁₃N₅O
• 分子量: 327.345
• InChiKey: CWLBHIMBKQEBAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-amino-3-cyano-4-methyl-5-phenylpyrrole 在 水 、 溶剂黄146 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 7-Methyl-4-oxo-3,6-diphenyl-pyrrolo[2,1-d][1,2,3,5]tetrazine-8-carbonitrile
  参考文献：
  名称：

  Pyrrolo[2,1-d][1,2,3,5]tetrazines, a New Class of Azolotetrazines Related to the Antitumor Drug Temozolomide

  摘要：

  DOI：

  10.1055/s-1999-3628

文献信息

• Pyrrolo[2,1-d][1,2,3,5]tetrazine-4(3h)-ones, a new class of azolotetrazines with potent antitumor activity
  作者：Patrizia Diana、Paola Barraja、Antonino Lauria、Alessandra Montalbano、Anna Maria Almerico、Gaetano Dattolo、Girolamo Cirrincione

  DOI：10.1016/s0968-0896(03)00145-7

  日期：2003.5.29

  Pyrrolo[2,1-d][1,2,3,5]tetrazinones 10a-o, compounds that hold the deaza skeleton of the antitumor drug temozolomide, were prepared by reaction of 2-diazopyrroles 9 and isocyanates. Such a synthetic route represents, among those leading to azolo-tetrazinones reported so far, the only possible one since attempts to cyclize to the title ring system 2-amino-1-carbamoylpyrroles 11 or the mono substituted 2-triazenopyrrole 12 failed. Compounds 10 were screened at the National Cancer Institute (NCI) for their activity against a panel of about 60 human tumor cell lines. Most of them possess remarkable antineoplastic activity having 6150 values in the low micromolar or sub-micromolar range and reaching, in the case of compound 10d, nanomolar concentrations. The most sensitive cell lines were MDA-N and MDA-MB-435 of the breast sub-panel, and SR, K-562, HL60 (TB) and CCRF-CEM of the leukaemia sub-panel. SAR evaluation and COMPARE computations indicate, for compounds 10, a mechanism of action different from that of temozolomide. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Pyrrolo[2,1-d][1,2,3,5]tetrazines, a New Class of Azolotetrazines Related to the Antitumor Drug Temozolomide
  作者：Patrizia Diana

  DOI：10.1055/s-1999-3628

  日期：1999.12