3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one | 92161-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one
• 英文别名: 2-(o-Chlor-phenyl)-3-amino-4-chinazolinon；3-Amino-2-<2-chlor-phenyl>-chinazolon-(4)；3-amino-2-(2-chloro-phenyl)-3H-quinazolin-4-one；3-Amino-2-(2-chlorophenyl)quinazolin-4-one
• CAS: 92161-79-0
• 化学式: C₁₄H₁₀ClN₃O
• 分子量: 271.706
• InChiKey: DFQNEVQVEIIPDN-UHFFFAOYSA-N

物化性质

• 沸点：
  464.8±47.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯磺酰氯 、 3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one 在 potassium hydroxide 作用下， 以60%的产率得到N-[2-(2-chlorophenyl)-4-oxoquinazolin-3(4H)-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents

  摘要：

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.

  DOI：

  10.3109/14756366.2013.845820
• 作为产物：
  描述：

  N-(2-chlorobenzoyl)anthranilic acid 在 乙酸酐 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents

  摘要：

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.

  DOI：

  10.3109/14756366.2013.845820

文献信息

• Synthesis and antitubercular activity of novel pyrazole–quinazolinone hybrid analogs
  作者：Unnat Pandit、Amit Dodiya

  DOI：10.1007/s00044-012-0351-0

  日期：2013.7

  A series of 2-(substituted-phenyl)-3-(((3-(pyridin-4-yl)-1-(p-tolyl)-1H-pyrazol-4-yl)methylene)amino)-quinazolin-4(3H)-ones have been synthesized. The structures of the synthesized compounds were assigned on the basis of IR, H-1 NMR, C-13 NMR, and mass spectral data, while their abilities to inhibit growth of Mycobacterium tuberculosis in vitro have been determined. The results show that compounds 5a, 5c, 5d, 5g, and 5k exhibited excellent antitubercular activity with percentage inhibition of 96, 90, 94, 93, and 92, respectively at a minimum inhibitory concentration (MIC) of < 6.25 mu g/mL, whereas compounds 5b, 5e, 5f, 5h, 5i, 5j, and 5l exhibited moderate- to- good antitubercular activity with percentage inhibition of 68, 70, 67, 64, 59, 73, and 67, respectively, at a MIC of > 6.25 mu g/mL. From the secondary screening, the actual MIC of compounds 5a, 5c, 5d, 5g, and 5k are < 3.125.
• Abdo, M. Anwar.; Abdel-Megeed, M. Farghaly; Saleh, M. Atia., Polish Journal of Chemistry, 1995, vol. 69, # 4, p. 583 - 590
  作者：Abdo, M. Anwar.、Abdel-Megeed, M. Farghaly、Saleh, M. Atia.、El-Hiti, G. Abdel-Rahman

  DOI：——

  日期：——
• Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents
  作者：Mujeeb Ur Rahman、Ankita Rathore、Anees A. Siddiqui、Gazala Parveen、M. Shahar Yar

  DOI：10.3109/14756366.2013.845820

  日期：2014.10.1

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.