3-allyl-2,3-dihydro-6-methyl-2-thioxoquinazolin-4(1H)-one | 104996-60-3

• 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: 3-allyl-2,3-dihydro-6-methyl-2-thioxoquinazolin-4(1H)-one
• 英文别名: 3-allyl-6-methyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one；3-Allyl-6-methyl-2-thioxo-2,3-dihydro-1H-chinazolin-4-on；6-methyl-3-prop-2-enyl-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 104996-60-3
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: NUBJBXLVKJMDMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-allyl-2,3-dihydro-6-methyl-2-thioxoquinazolin-4(1H)-one 在 溴 作用下， 生成 2-bromomethyl-7-methyl-2,3-dihydro-thiazolo[2,3-b]quinazolin-5-one
  参考文献：
  名称：

  Dhami et al., Journal Of Scientific and Industrial Research, 1957, vol. 16 B, p. 311,313

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 、 天然芥菜籽油 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以92%的产率得到3-allyl-2,3-dihydro-6-methyl-2-thioxoquinazolin-4(1H)-one
  参考文献：
  名称：

  Quinazoline–sulfonamides with potent inhibitory activity against the α-carbonic anhydrase from Vibrio cholerae

  摘要：

  Thirteen novel sulfonamide derivatives incorporating the quinazoline scaffold were synthesized by simple, eco-friendly procedures. These compounds were tested for their ability to inhibit the alpha-carbonic anhydrases (CA, EC 4.2.1.1) from Vibrio cholerae (VchCA) as well as the human alpha-CA isoforms, hCA I and hCA II. Nine compounds were highly effective, nanomolar inhibitors of the pathogenic enzyme VchCA. Three of them were also highly effective sub-nanomolar inhibitors of the cytosolic isoform II. The best VchCA inhibitor had a K-I of 2.7 nM. Many of these developed compounds showed high selectivity for inhibition of the bacterial over the mammalian CA isoforms, with one compound possessing selectivity ratios as high as 97.9 against hCA I and 9.7 against hCA II. Compound 9d was another highly effective VchCA inhibitor presenting a selectivity ratio of 99.1 and 8.1 against hCA I and hCA II, respectively. These results suggest that sulfonamides with quinazoline backbone could be considered suitable tools to better understand the role of bacterial CAs in pathogenesis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.015