3-{5-[(E)-(4-chloro-2-hydroxyphenyl)diazenyl]-4-methyl-6-oxo-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl}-2-(chloromethyl)quinazolin-4(3H)-one | 1319147-76-6

• 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-{5-[(E)-(4-chloro-2-hydroxyphenyl)diazenyl]-4-methyl-6-oxo-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl}-2-(chloromethyl)quinazolin-4(3H)-one
• CAS: 1319147-76-6
• 化学式: C₂₀H₁₄Cl₂N₆O₃S
• 分子量: 489.342
• InChiKey: XWMAZVGWOIQOGT-OCEACIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  112.51
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-氨基-5-氯苯酚 在 盐酸 、 sodium ethanolate 、 sodium nitrite 作用下， 以 吡啶 、 水 为溶剂， 反应 9.0h， 生成 3-{5-[(E)-(4-chloro-2-hydroxyphenyl)diazenyl]-4-methyl-6-oxo-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl}-2-(chloromethyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Exploration of antimicrobial and antioxidant potential of newly synthesized 2,3-disubstituted quinazoline-4(3H)-ones

  摘要：

  A series of 2-(chloromethyl)-3-(4-methyl-6-oxo-5-[(E)-phenyldiazenyl]-2-thioxo-5,6-dihydropyrimidine-1(2H)-yl)quinazoline-4(3H)-ones 9a-j was synthesized by treating 2-(chloroacetyl) amino benzoic acid with 3-amino-6-methyl-5-[(E)-phenyldiazenyl]-2-thioxo-2,5-dihydropyrimidine-4(3H)-one 8a-j and was screened for in vitro antibacterial activities against a representative panel of Gram-positive and Gram-negative bacteria. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, H-1 NMR, Mass and elemental analysis data. All the synthesized compounds elicited the potent inhibitory action against all the tested bacterial stains. Furthermore, in order to explore the antioxidant potential of newly synthesized compounds, the free radical scavenging activity measurement were performed by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay method. It is revealed from the antioxidant screening results that the compounds 9c and f manifested profound antioxidant potential. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.031

文献信息

• Exploration of antimicrobial and antioxidant potential of newly synthesized 2,3-disubstituted quinazoline-4(3H)-ones
  作者：Ashok Kumar、Pratibha Sharma、Prerna Kumari、Bhagwan Lal Kalal

  DOI：10.1016/j.bmcl.2011.05.031

  日期：2011.7

  A series of 2-(chloromethyl)-3-(4-methyl-6-oxo-5-[(E)-phenyldiazenyl]-2-thioxo-5,6-dihydropyrimidine-1(2H)-yl)quinazoline-4(3H)-ones 9a-j was synthesized by treating 2-(chloroacetyl) amino benzoic acid with 3-amino-6-methyl-5-[(E)-phenyldiazenyl]-2-thioxo-2,5-dihydropyrimidine-4(3H)-one 8a-j and was screened for in vitro antibacterial activities against a representative panel of Gram-positive and Gram-negative bacteria. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, H-1 NMR, Mass and elemental analysis data. All the synthesized compounds elicited the potent inhibitory action against all the tested bacterial stains. Furthermore, in order to explore the antioxidant potential of newly synthesized compounds, the free radical scavenging activity measurement were performed by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay method. It is revealed from the antioxidant screening results that the compounds 9c and f manifested profound antioxidant potential. (C) 2011 Elsevier Ltd. All rights reserved.