4-[2-thioxo-1,2,3,4-tetrahydroquinazolin-4-on-3-yl]benzenesulfonamide | 92164-73-3

• 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: 4-[2-thioxo-1,2,3,4-tetrahydroquinazolin-4-on-3-yl]benzenesulfonamide
• 英文别名: 4-(4-oxo-2-thioxo-1,2-dihydroquinazolin-3(4H)-yl)benzene sulfonamide；4-(4-oxo-2-thioxo-1,4-dihydro-2H-quinazolin-3-yl)-benzenesulfonamide；4-Oxo-2-thioxo-3-<4-sulfamoyl-phenyl>-1.2.3.4-tetrahydro-chinazolin；4-(4-oxo-2-sulfanylidene-1H-quinazolin-3-yl)benzenesulfonamide
• CAS: 92164-73-3
• 化学式: C₁₄H₁₁N₃O₃S₂
• 分子量: 333.392
• InChiKey: NABGQEWOUKHHHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[2-thioxo-1,2,3,4-tetrahydroquinazolin-4-on-3-yl]benzenesulfonamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到4-(2-hydrazinyl-4-oxoquinazolin-3-yl)benzenesulfonamide
  参考文献：
  名称：

  一些含有磺酰氨基部分的新型硫脲、萘并[2,3-d]噻唑、喹唑啉和噻吩并[2,3-d]嘧啶衍生物的合成和抗菌活性

  摘要：

  摘要 对取代的氨磺酰基苯基异硫氰酸酯 1a-d 是使用报道的程序制备的。研究了 1a-d 对一些含氮亲核试剂的反应性。因此，1 与芳香胺和邻氨基苯甲酸的相互作用提供了 N1,N3-二取代硫脲 2a-c 和 3-[4-N-取代磺酰氨基]苯基-2-thioxo-4-(3H)-quinazolin-4-ones 4a -f，分别。在含有无水碳酸钾的丙酮中用氯乙酸乙酯将 4c 烷基化得到喹唑啉 5。使用乙醇水合肼对 5 进行肼解得到相应的酰肼 6。最后，用 2-氨基-3-氰基-4 处理 1a、b、d ,5,6,7-四氢苯并[b]噻吩生成含有磺酰氨基部分的噻吩并[2,3-d]嘧啶10a-c。新化合物的结构是通过元素分析和光谱数据确定的。还，

  DOI：

  10.1080/10426500008045000
• 作为产物：
  描述：

  dimethyl N-<4-(4-oxo-2-thioxo-1,2,3,4-tetrahydro-3-quinazolinylphenylsulphonyl)>dithiocarbonoimidate 在 盐酸 作用下， 反应 2.0h， 以76%的产率得到4-[2-thioxo-1,2,3,4-tetrahydroquinazolin-4-on-3-yl]benzenesulfonamide
  参考文献：
  名称：

  SOME ASPECTS ON ACYCLO- 4-[QUINAZOLIN-3-YL]BENZENESULFONAMIDE NON-NUCLEOSIDES SYNTHESIS

  摘要：

  The reaction of 4-[1,2,3,4-tetrahydroquinazolin-2,4-dion-3-yl]benzenesulfonamide 4 and 4-[2-thioxo-1,2,3,4 tetrahydroquniazolin-4-on-3-yl]benznesulfonamide 5 with chloromethylethyl ether; chloromethylbenzyl ether; and (2-acetoxyethoxy)methyl bromide afforded compounds 7a-c, 8a,b, and 13 which are analogues to MKC-442, TNK 561, and HEPT.

  DOI：

  10.1080/10426500490459678

文献信息

• Exploration of N-alkyl-2-[(4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-yl)thio]acetamide derivatives as anticancer and radiosensitizing agents
  作者：Aiten M. Soliman、Mostafa M. Ghorab

  DOI：10.1016/j.bioorg.2019.102956

  日期：2019.7

  of 0.34-149.10 µM. The inhibition percentage of VEGFR-2 was measured for all the compounds and found to be in the range of 90.09-20.44%. The promising compounds 8, 12, 13, 16 and 17 were selected to measure their possible multikinase inhibitory activity against VEGFR-2 and EGFR. IC50 of the promising compounds were in the range of 247-793 nM for VEGFR-2 in reference to sunitinib (IC50 320 nM), and 369-725 nM

  多靶点治疗被认为是成功的癌症治疗方法。通过杂交策略开发小分子多激酶抑制剂可以提供高效且选择性的抗癌药。设计并合成了N-烷基-2-[（4-氧代-3-（4-氨磺酰基苯基）-3,4-二氢喹唑啉-2-基）硫代]乙酰胺衍生物5-18的文库。筛选合成的化合物对MDA-MB-231乳腺癌细胞系的细胞毒活性，显示IC50为0.34-149.10 µM。测量所有化合物的VEGFR-2抑制百分数，发现其在90.09-20.44％的范围内。选择有希望的化合物8、12、13、16和17来测量其针对VEGFR-2和EGFR的可能的多激酶抑制活性。相对于舒尼替尼（IC50 320 nM），VEGFR-2的有希望化合物的IC50为247-793 nM，相对于厄洛替尼（IC50 568 nM），EGFR的IC50为369-725 nM。化合物12和13分别显示出对VEGFR-2和EGFR最有效的活性。测量12和13对MC
• Subudhi; Panda; Ghosh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 6, p. 899 - 903
  作者：Subudhi、Panda、Ghosh、Panda

  DOI：——

  日期：——
• Antioxidant activity of novel quinazolinones bearing sulfonamide: Potential radiomodulatory effects on liver tissues via NF-κB/ PON1 pathway
  作者：Aiten M. Soliman、Heba M. Karam、Mai H. Mekkawy、Mostafa M. Ghorab

  DOI：10.1016/j.ejmech.2020.112333

  日期：2020.7

  In order to discover new antioxidants, fifteen novel quinazolinone derivatives bearing benzenesulfonamide moiety with variable heterocyclic tail, were synthesized and their structures were established on the basis of spectral data. All the synthesized compounds were screened for their antioxidant potential using DPPH assay in comparison to ascorbic acid. The N-(pyrazin-2-yl)-2-[(4-oxo-3-(4-sulfamoylphenyl)-3,4-dihydroquinazolin-2-yl)thio]acetamide 16 was the most active scaffold in this series with greater scavenging activity than that of ascorbic acid. In vivo acute toxicity study of compound 16 indicates its relative safety with a median lethal dose of 200 mg/kg. The possible antioxidant and hepatoprotective activities of compound 16 were evaluated in irradiated mice. Compound 16 caused mitigation of gamma radiation-induced oxidative stress verified by the decline in MDA, ROS and NF-kappa B levels. Moreover, SOD and PON1 activities, as well as Zn2+ levels, were improved in liver tissues. Furthermore, molecular docking of compound 16 inside the active site of SOD and PON1 demonstrated the same binding interactions as that of the co-crystallized ligands considering the binding possibilities and energy scores. These findings support that compound 16 may represent a structural lead for developing new antioxidants and hepatoprotective agents. (C) 2020 Elsevier Masson SAS. All rights reserved.
• Antiproliferative, antiangiogenic and apoptotic effect of new hybrids of quinazoline-4(3H)-ones and sulfachloropyridazine
  作者：Sally S. Zahran、Fatma A. Ragab、Marwa G. El-Gazzar、Aiten M. Soliman、Walaa R. Mahmoud、Mostafa M. Ghorab

  DOI：10.1016/j.ejmech.2022.114912

  日期：2023.1
• SOME ASPECTS ON ACYCLO- 4-[QUINAZOLIN-3-YL]BENZENESULFONAMIDE NON-NUCLEOSIDES SYNTHESIS
  作者：Abd El-Hamid、A. A. Ismail

  DOI：10.1080/10426500490459678

  日期：2004.6

  The reaction of 4-[1,2,3,4-tetrahydroquinazolin-2,4-dion-3-yl]benzenesulfonamide 4 and 4-[2-thioxo-1,2,3,4 tetrahydroquniazolin-4-on-3-yl]benznesulfonamide 5 with chloromethylethyl ether; chloromethylbenzyl ether; and (2-acetoxyethoxy)methyl bromide afforded compounds 7a-c, 8a,b, and 13 which are analogues to MKC-442, TNK 561, and HEPT.