2-肼基-3-甲基喹唑啉-4(3h)-酮 | 61507-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-肼基-3-甲基喹唑啉-4(3h)-酮
• 英文名称: 2-hydrazino-3-methylquinazolin-4(3H)-one
• 英文别名: 2-hydrazinyl-3-methylquinazolin-4-one
• CAS: 61507-80-0
• 化学式: C₉H₁₀N₄O
• mdl: MFCD01219687
• 分子量: 190.205
• InChiKey: BQDOAXFBKRUNTF-UHFFFAOYSA-N

物化性质

• 溶解度：
  >28.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-肼基-3-甲基喹唑啉-4(3h)-酮 在 iron(III) chloride 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 1-(3,4-dibenzyloxyphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinazolin-5-one
  参考文献：
  名称：

  Synthesis of triazoloquinazolinone based compounds as tubulin polymerization inhibitors and vascular disrupting agents

  摘要：

  A series of 1-phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5-ones designed as conformationally restricted CA 4 analogues, were tested for their tubulin polymerization and growth inhibitory activities. The 3-hydroxy-4-methoxy derivatives 11d and 12d are potent inhibitors of tubulin assembly but only the N-methylated amid counterpart 12d possesses potent anticancer activity in a large panel of cancer cell lines. Upon treatment with compound 12d, remarkable cell shape changes as cell migration and tube formation were elicited in HUVECs, consistent with vasculature damaging activity. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.056
• 作为产物：
  描述：

  2-异硫氰基苯甲酸甲酯 在 一水合肼 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 2-肼基-3-甲基喹唑啉-4(3h)-酮
  参考文献：
  名称：

  Synthesis of triazoloquinazolinone based compounds as tubulin polymerization inhibitors and vascular disrupting agents

  摘要：

  A series of 1-phenyl-[1,2,4]triazolo[4,3-a]quinazolin-5-ones designed as conformationally restricted CA 4 analogues, were tested for their tubulin polymerization and growth inhibitory activities. The 3-hydroxy-4-methoxy derivatives 11d and 12d are potent inhibitors of tubulin assembly but only the N-methylated amid counterpart 12d possesses potent anticancer activity in a large panel of cancer cell lines. Upon treatment with compound 12d, remarkable cell shape changes as cell migration and tube formation were elicited in HUVECs, consistent with vasculature damaging activity. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.056

文献信息

• Regioselectivity of Electrophilic Attack on 4-Methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one. Part 1: Reactions at the Sulfur Atom
  作者：Walid Fathalla、Michal Čajan、Pavel Pazdera

  DOI：10.3390/60600557

  日期：——

  The regioselectivity of the model compound 4-methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one (3) towards different electrophiles was studied. Compound 3 reacts with alkyl and aryl halides to give the corresponding S-substituted derivatives. The reaction of the model thioamide with acyl halides proceeds by the formation of kinetically controlled S-acyl derivatives followed by a transacylation reaction to give the N2-acyl derivatives as thermodynamically controlled products. Theoretical DFT computational studies supported the explanation of these results. The synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, and mass spectroscopy.

  对模型化合物4-甲基-1-硫酮-1,2,4,5-四氢[1,2,4]三唑并[4,3-a]喹唑啉-5-酮（3）对不同亲电试剂的区域选择性进行了研究。化合物3与烷基和芳基卤化物反应生成相应的S-取代衍生物。模型硫酰胺与酰卤的反应过程是先生成动力学控制的S-酰基衍生物，随后通过酰基转移反应生成热力学控制的N2-酰基衍生物。理论DFT计算研究支持了这些结果的解释。合成的化合物通过FTIR、1H-NMR、13C-NMR和质谱进行了表征。
• Synthesis of New 4(3H)-Quinazolinone Derivatives Using 5(4H)-Oxazolones
  作者：Hooshang Hamidian、Ahmad Tikdari、Hojatollah Khabazzadeh

  DOI：10.3390/11050377

  日期：——

  New derivatives of 5(4H)-quinazolinone containing 2-imidazolin-5-one rings have been prepared from 5(4H)-oxazolone derivatives.

  已从 5(4H)-恶唑酮衍生物制备了含有 2-咪唑啉-5-酮环的 5(4H)-喹唑啉酮的新衍生物。
• Synthesis, Anti-inflammatory and Analgesic Synthesis, Anti-inflammatory and Analgesic New 4(3H)-Quinazolinone Derivatives
  作者：Akgül Yeşilada、Semra Koyunoğlu、Nezire Saygılıa、Esra Kupeli、Erdem Yeşilada、Erdal Bedir、Ikhlas Khanc

  DOI：10.1002/ardp.200200752

  日期：2004.2

  derivatives have been shown to have analgesic and anti‐inflammatory properties. In this study, 14 new 3‐methyl‐4(3H)quinazolinone derivatives bearing 2‐[1′‐phenyl‐3′‐(substituted‐phenyl)‐2′‐propenylidene]hydrazino or 2[5′‐(substituted phenyl)‐3′‐phenyl‐2′‐pyrazolin‐1′‐yl] groups have been synthesized with the aim of obtaining new analgesic and anti‐inflam matory leads. The structures were elucidated

  4 (3H)-喹唑啉酮和吡唑衍生物已被证明具有镇痛和抗炎特性。本研究中，14个新的3-甲基-4(3H)喹唑啉酮衍生物带有2-[1'-苯基-3'-(取代-苯基)-2'-亚丙烯]肼基或2[5'-(取代苯基) -3'-苯基-2'-吡唑啉-1'-基]基团已被合成，目的是获得新的镇痛和抗炎线索。通过UV、IR、1H-NMR、13C-NMR、质谱和元素分析数据对其结构进行了阐明。通过角叉菜胶诱导的小鼠后爪水肿试验测定合成化合物的抗炎活性。所有化合物均显示出统计学上显着的效果。对于镇痛活性评估，对苯醌诱导的扭体试验应用于小鼠。
• Synthesis and structure of as-triazinoquinazolines. 3
  作者：Mohamed A. Badawy、Sayed A. Abdel-Hady、Ahamed H. Mahmoud、Yehia A. Ibrahim

  DOI：10.1021/jo00288a060

  日期：1990.1
• Badawy, Mohamed A.; Abdel-Hady, Sayed A.; Mahmoud, Ahmed H., Liebigs Annalen der Chemie, 1990, # 8, p. 815 - 817
  作者：Badawy, Mohamed A.、Abdel-Hady, Sayed A.、Mahmoud, Ahmed H.、Ibrahim, Yehia A.

  DOI：——

  日期：——