1-(4-methyl-2-nitrophenyl)-5-methylpyrazol-3-one | 851517-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methyl-2-nitrophenyl)-5-methylpyrazol-3-one
• 英文别名: 3-methyl-2-(4-methyl-2-nitrophenyl)-1H-pyrazol-5-one
• CAS: 851517-44-7
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: WDZHTDAAWKYVFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methyl-2-nitrophenyl)-5-methylpyrazol-3-one 在 palladium on activated charcoal 硫酸 、 氢气 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 生成 1,7-Dimethyl-3a,4,5,9b-tetraaza-cyclopenta[a]naphthalen-3-one
  参考文献：
  名称：

  1-Methyl-3H-pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones. Design, Synthesis, and Biological Activity of New Antitumor Agents

  摘要：

  1-Methylpyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones 4, synthesized in good to excellent yields, were designed as novel alkylating agents because of their peculiar chemical behavior. All derivatives showed antiproliferative activity against more than 50 types of tumor cell lines with GI(50) reaching sub-micromolar values. SAR studies revealed that the presence of a chlorine atom is well-tolerated in both positions 8 and 9, whereas in the case of the methyl group, switching from the 8 to the 9 position gives rise to the most active compound of the series, 4g, either for the number of cell lines inhibited and for selectivity against leukaemia and renal cancer subpanels. COMPARE and 3D-MIND computations indicate, for compounds 4, an activity profile analogous to rifamycins and cytidine analogues.

  DOI：

  10.1021/jm049075u
• 作为产物：
  描述：

  4-甲基-2-硝基苯胺 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.0h， 生成 1-(4-methyl-2-nitrophenyl)-5-methylpyrazol-3-one
  参考文献：
  名称：

  探索吡唑并[1,2- a ]苯并[1,2,3,4]四嗪-3-酮衍生物的抗癌潜力：对细胞凋亡诱导，细胞周期和增殖的影响

  摘要：

  为了研究它们的抗癌潜力，通过化学计量学方法VLAK设计了四种新的吡唑并[1,2- a ]苯并[1,2,3,4]四嗪酮衍生物和先前系列中活性最高的三种化合物评估了一些细胞事件，包括增殖，凋亡诱导和细胞周期。NCI一剂（10μM）筛选显示8,9-二甲基衍生物显示出对白血病（CCRF-CEM）和结肠癌细胞系（COLO 205）的活性，分别达到了81％和45％的生长抑制（GI） ）， 分别。用两个氯原子取代两个甲基可维持对白血病细胞的活性（CCRF-CEM，GI 77％），并选择性增强针对COLO 205的活性，达到LD 50在μM范围内，相对于SW-620，GI为77％。有趣的是，观察到针对治疗性“难治性”非小细胞肺癌（NCI-H522）的可观的47％的生长抑制。此外，基于线粒体膜去极化的凋亡诱导作用被发现在HeLa细胞的EC 50 3–5μM范围内，证明与相关的体外存在明确的关系。针对NCI肿

  DOI：

  10.1016/j.ejmech.2013.03.046

文献信息

• Exploring the anticancer potential of pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-one derivatives: The effect on apoptosis induction, cell cycle and proliferation
  作者：Francesco Mingoia、Caterina Di Sano、Francesco Di Blasi、Marco Fazzari、Annamaria Martorana、Anna Maria Almerico、Antonino Lauria

  DOI：10.1016/j.ejmech.2013.03.046

  日期：2013.6

  anticancer potential, four new pyrazolo[1,2-a]benzo[1,2,3,4]tetrazinone derivatives, designed through the chemometric protocol VLAK, and three of the most active compounds of the previous series have been evaluated on some cellular events including proliferation, apoptosis induction, and cell cycle. The NCI one dose (10 μM) screening revealed that the 8,9-di-methyl derivative showed activity against Leukemia

  为了研究它们的抗癌潜力，通过化学计量学方法VLAK设计了四种新的吡唑并[1,2- a ]苯并[1,2,3,4]四嗪酮衍生物和先前系列中活性最高的三种化合物评估了一些细胞事件，包括增殖，凋亡诱导和细胞周期。NCI一剂（10μM）筛选显示8,9-二甲基衍生物显示出对白血病（CCRF-CEM）和结肠癌细胞系（COLO 205）的活性，分别达到了81％和45％的生长抑制（GI） ）， 分别。用两个氯原子取代两个甲基可维持对白血病细胞的活性（CCRF-CEM，GI 77％），并选择性增强针对COLO 205的活性，达到LD 50在μM范围内，相对于SW-620，GI为77％。有趣的是，观察到针对治疗性“难治性”非小细胞肺癌（NCI-H522）的可观的47％的生长抑制。此外，基于线粒体膜去极化的凋亡诱导作用被发现在HeLa细胞的EC 50 3–5μM范围内，证明与相关的体外存在明确的关系。针对NCI肿
• 1-Methyl-3<i>H</i>-pyrazolo[1,2-<i>a</i>]benzo[1,2,3,4]tetrazin-3-ones. Design, Synthesis, and Biological Activity of New Antitumor Agents
  作者：Anna Maria Almerico、Francesco Mingoia、Patrizia Diana、Paola Barraja、Antonino Lauria、Alessandra Montalbano、Girolamo Cirrincione、Gaetano Dattolo

  DOI：10.1021/jm049075u

  日期：2005.4.1

  1-Methylpyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones 4, synthesized in good to excellent yields, were designed as novel alkylating agents because of their peculiar chemical behavior. All derivatives showed antiproliferative activity against more than 50 types of tumor cell lines with GI(50) reaching sub-micromolar values. SAR studies revealed that the presence of a chlorine atom is well-tolerated in both positions 8 and 9, whereas in the case of the methyl group, switching from the 8 to the 9 position gives rise to the most active compound of the series, 4g, either for the number of cell lines inhibited and for selectivity against leukaemia and renal cancer subpanels. COMPARE and 3D-MIND computations indicate, for compounds 4, an activity profile analogous to rifamycins and cytidine analogues.