8-chloro-3-phenylpyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide | 244234-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-chloro-3-phenylpyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
• 英文别名: 8-Chloro-5-oxido-3-phenylpyrazolo[5,1-c][1,2,4]benzotriazin-5-ium
• CAS: 244234-16-0
• 化学式: C₁₅H₉ClN₄O
• 分子量: 296.716
• InChiKey: DBDAEDIPRACXJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 8-chloro-3-phenylpyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以20%的产率得到8-(4-methylpiperazin-1-yl)-3-phenylpyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
  参考文献：
  名称：

  新型吡唑并[5,1-c] [1,2,4]苯并三嗪，吡唑并[5,1-c]吡啶并[4,3-e] [1,2,4]三嗪及其开放类似物的合成具有细胞毒性常氧和低氧条件下的药物。

  摘要：

  报道了一系列吡唑并[5,1-c] [1,2,4]苯并三嗪及其相关类似物在常氧和低氧条件下的合成和抗肿瘤活性。所有化合物均在人大肠腺癌细胞系HCT-8和化合物15和20上进行了测试，化合物15和20在低氧和常氧条件下分别显示出选择性的细胞毒性，测定了ROS的产生，细胞周期和DNA片段化。这项初步研究鼓励我们将15和20视为进一步优化的有趣线索。

  DOI：

  10.1016/j.bmc.2008.09.055
• 作为产物：
  描述：

  2-硝基-5-氯苯基肼 在 盐酸 、 sodium hydroxide 、 水 作用下， 以 乙醇 、 二乙二醇二甲醚 为溶剂， 反应 60.0h， 生成 8-chloro-3-phenylpyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide
  参考文献：
  名称：

  Benzodiazepine receptor ligands

  摘要：

  A new series of 2- and/or 3-substituted pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides and their 8-chloro derivatives were synthesized, and their benzodiazepine receptor (BZR) affinities were evaluated in vitro in comparison to lead compound 3-ethoxycarbonyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine-5-oxide (29) [1,2]. None of the new compounds showed significant affinity for BZR. On the basis of a pharmacophore/receptor model suggested for lead compound 29, some hypotheses to explain the inactivity of new derivatives are discussed. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00044-0

文献信息

• Synthesis of new pyrazolo[5,1-c][1,2,4] benzotriazines, pyrazolo[5,1-c]pyrido[4,3-e][1,2,4] triazines and their open analogues as cytotoxic agents in normoxic and hypoxic conditions
  作者：Giovanna Ciciani、Marcella Coronnello、Gabriella Guerrini、Silvia Selleri、Miriam Cantore、Paola Failli、Enrico Mini、Annarella Costanzo

  DOI：10.1016/j.bmc.2008.09.055

  日期：2008.11

  The synthesis and antitumor activity in normoxic and hypoxic conditions of a series of pyrazolo[5,1-c][1,2,4]benzotriazine and its related analogues are reported. All compounds were tested on human colorectal adenocarcinoma cell line HCT-8 and for compounds 15 and 20, which show to have selective cytotoxicity in hypoxic and in normoxic conditions respectively, ROS production, cell cycle, and DNA fragmentation

  报道了一系列吡唑并[5,1-c] [1,2,4]苯并三嗪及其相关类似物在常氧和低氧条件下的合成和抗肿瘤活性。所有化合物均在人大肠腺癌细胞系HCT-8和化合物15和20上进行了测试，化合物15和20在低氧和常氧条件下分别显示出选择性的细胞毒性，测定了ROS的产生，细胞周期和DNA片段化。这项初步研究鼓励我们将15和20视为进一步优化的有趣线索。
• Benzodiazepine receptor ligands
  作者：G. Guerrini、A. Costanzo、F. Bruni、G. Ciciani、S. Selleri、P. Gratteri、B. Costa、C. Martini、A. Lucacchini

  DOI：10.1016/s0014-827x(99)00044-0

  日期：1999.6

  A new series of 2- and/or 3-substituted pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides and their 8-chloro derivatives were synthesized, and their benzodiazepine receptor (BZR) affinities were evaluated in vitro in comparison to lead compound 3-ethoxycarbonyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine-5-oxide (29) [1,2]. None of the new compounds showed significant affinity for BZR. On the basis of a pharmacophore/receptor model suggested for lead compound 29, some hypotheses to explain the inactivity of new derivatives are discussed. (C) 1999 Elsevier Science S.A. All rights reserved.