2'-羟基甲喹酮 | 5060-50-4

• 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'-羟基甲喹酮
• 英文名称: 3-(2-(hydroxylmethyl)phenyl)-2-methylquinazolin-4(3H)-one
• 英文别名: 2-Methyl-3-<2-hydroxymethyl-phenyl>-4(3H)-chinazolinon；3-(2-hydroxymethyl-phenyl)-2-methyl-3H-quinazolin-4-one；4(3H)-Quinazolinone, 3-(alpha-hydroxy-o-tolyl)-2-methyl-；3-[2-(hydroxymethyl)phenyl]-2-methylquinazolin-4-one
• CAS: 5060-50-4
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: VHBSPUXYKQNPJR-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C(Solv: methanol (67-56-1))
• 沸点：
  473.2±47.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

羟基甲基喹酮是甲基喹酮的一个已知人体代谢物。

Hydroxy-methaqualone is a known human metabolite of methaqualone.

来源:NORMAN Suspect List Exchange

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2'-羟基甲喹酮 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 2-methyl-3-(2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Luotonin-A based quinazolinones cause apoptosis and senescence via HDAC inhibition and activation of tumor suppressor proteins in HeLa cells

  摘要：

  A series of novel quinazolinone hybrids were synthesized by employing click chemistry and evaluated for anti-proliferative activities against MCF-7, HeLa and 1(562 cell lines. Among these cell lines, HeLa cells were found to respond effectively to these quinazolinone hybrids with IC50 values ranging from 5.94 to 16.45 mu M. Some of the hybrids (4q, 4r, 4e, 4k, 4t, 4w) with promising anti-cancer activity were further investigated for their effects on the cell cycle distribution. FACS analysis revealed the G1 cell cycle arrest nature of these hybrids. Further to assess the senescence inducing ability of these compounds, a senescence associated beta-gal assay was performed. The senescence inducing nature of these compounds was supported by the effect of hybrid (4q) on p16 promoter activity, the marker for senescence. Moreover, cells treated with most effective compound (4q) show up-regulation of p53, p21 and down-regulation of HDAC-1, HDAC-2, HDAC-5 and EZH2 mRNA levels. Docking results suggest that, the triazole nitrogen showed Zn+2 mediated interactions with the histidine residue of HDACs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.057
• 作为产物：
  描述：

  邻氨基苯甲醇 、 邻乙酰胺苯甲酸內酯 在 四丁基溴化铵 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 生成 2'-羟基甲喹酮
  参考文献：
  名称：

  Luotonin-A based quinazolinones cause apoptosis and senescence via HDAC inhibition and activation of tumor suppressor proteins in HeLa cells

  摘要：

  A series of novel quinazolinone hybrids were synthesized by employing click chemistry and evaluated for anti-proliferative activities against MCF-7, HeLa and 1(562 cell lines. Among these cell lines, HeLa cells were found to respond effectively to these quinazolinone hybrids with IC50 values ranging from 5.94 to 16.45 mu M. Some of the hybrids (4q, 4r, 4e, 4k, 4t, 4w) with promising anti-cancer activity were further investigated for their effects on the cell cycle distribution. FACS analysis revealed the G1 cell cycle arrest nature of these hybrids. Further to assess the senescence inducing ability of these compounds, a senescence associated beta-gal assay was performed. The senescence inducing nature of these compounds was supported by the effect of hybrid (4q) on p16 promoter activity, the marker for senescence. Moreover, cells treated with most effective compound (4q) show up-regulation of p53, p21 and down-regulation of HDAC-1, HDAC-2, HDAC-5 and EZH2 mRNA levels. Docking results suggest that, the triazole nitrogen showed Zn+2 mediated interactions with the histidine residue of HDACs. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.057

文献信息

• Luotonin-A based quinazolinones cause apoptosis and senescence via HDAC inhibition and activation of tumor suppressor proteins in HeLa cells
  作者：Ramineni Venkatesh、M. Janaki Ramaiah、Hanmant K. Gaikwad、Sridhara Janardhan、Rajashaker Bantu、Lingaiah Nagarapu、G. Narahari Sastry、A. Raksha Ganesh、Manikapal Bhadra

  DOI：10.1016/j.ejmech.2015.02.057

  日期：2015.4

  A series of novel quinazolinone hybrids were synthesized by employing click chemistry and evaluated for anti-proliferative activities against MCF-7, HeLa and 1(562 cell lines. Among these cell lines, HeLa cells were found to respond effectively to these quinazolinone hybrids with IC50 values ranging from 5.94 to 16.45 mu M. Some of the hybrids (4q, 4r, 4e, 4k, 4t, 4w) with promising anti-cancer activity were further investigated for their effects on the cell cycle distribution. FACS analysis revealed the G1 cell cycle arrest nature of these hybrids. Further to assess the senescence inducing ability of these compounds, a senescence associated beta-gal assay was performed. The senescence inducing nature of these compounds was supported by the effect of hybrid (4q) on p16 promoter activity, the marker for senescence. Moreover, cells treated with most effective compound (4q) show up-regulation of p53, p21 and down-regulation of HDAC-1, HDAC-2, HDAC-5 and EZH2 mRNA levels. Docking results suggest that, the triazole nitrogen showed Zn+2 mediated interactions with the histidine residue of HDACs. (C) 2015 Elsevier Masson SAS. All rights reserved.