3-amino-6-bromo-2,3-dihydro-2-thioxo-4(1H)-quinazolinone | 314021-00-6

• 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-amino-6-bromo-2,3-dihydro-2-thioxo-4(1H)-quinazolinone
• 英文别名: 3-amino-6-bromo-2-thioxo-2,3-dihydroquinazolin-4(1H)-one；3-amino-6-bromo-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 314021-00-6
• 化学式: C₈H₆BrN₃OS
• 分子量: 272.125
• InChiKey: FZSAASAGUXWPPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-6-bromo-2,3-dihydro-2-thioxo-4(1H)-quinazolinone 在 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 N-(6-bromo-2-(methylthio)-4-oxoquinazolin-3(4H)-yl)methanesulfonamide
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and bioactivity evaluation of 6-bromo-quinazolinone derivatives

  摘要：

  6-Bromo-quinazolinone derivatives were prepared and evaluated for the ability to inhibit cyclooxygenase-2 (COX-2). An extensive structure-activity relationship work was carried out, thus some potent and selective COX-2 inhibitors were identified. The key compound isothiocyanate was prepared through a simple and ecological method using di-2-pyridyl thionocarbonate in substitution of the thiophosgene, a potential air pollutant. The cyclization reaction of intermediate derivatives was developed through the methods reporting by Wamhoff. The anti-inflammatory activity of the derivatives (5-12) was evaluated by determining (by Western blot) the expression of cyclooxygenase (COX)-2, of inducible NO synthase (iNOS) and of intercellular adhesion molecule-1 (ICAM-1). The biological assays showed that the derivatives 7, 9, 10, 12 act as potent inhibitors of COX-2, iNOS, and ICAM-1 expression in human keratinocytes NCTC-2544 cells. This work showed that the new derivatives could be used as a novel class of anti-inflammatory agents.

  DOI：

  10.1007/s00044-014-1311-7
• 作为产物：
  描述：

  sodium 3-amino-6-bromo-4-oxo-3,4-dihydroquinazoline-2-thiolate 在 盐酸 作用下， 以 水 为溶剂， 以60%的产率得到3-amino-6-bromo-2,3-dihydro-2-thioxo-4(1H)-quinazolinone
  参考文献：
  名称：

  Synthesis, structure–activity relationships, and bioactivity evaluation of 6-bromo-quinazolinone derivatives

  摘要：

  6-Bromo-quinazolinone derivatives were prepared and evaluated for the ability to inhibit cyclooxygenase-2 (COX-2). An extensive structure-activity relationship work was carried out, thus some potent and selective COX-2 inhibitors were identified. The key compound isothiocyanate was prepared through a simple and ecological method using di-2-pyridyl thionocarbonate in substitution of the thiophosgene, a potential air pollutant. The cyclization reaction of intermediate derivatives was developed through the methods reporting by Wamhoff. The anti-inflammatory activity of the derivatives (5-12) was evaluated by determining (by Western blot) the expression of cyclooxygenase (COX)-2, of inducible NO synthase (iNOS) and of intercellular adhesion molecule-1 (ICAM-1). The biological assays showed that the derivatives 7, 9, 10, 12 act as potent inhibitors of COX-2, iNOS, and ICAM-1 expression in human keratinocytes NCTC-2544 cells. This work showed that the new derivatives could be used as a novel class of anti-inflammatory agents.

  DOI：

  10.1007/s00044-014-1311-7

文献信息

• Santagati; Modica; Santagati, Pharmazie, 2000, vol. 55, # 10, p. 737 - 740
  作者：Santagati、Modica、Santagati、Cutuli、Mangano、Caruso

  DOI：——

  日期：——
• Synthesis, structure–activity relationships, and bioactivity evaluation of 6-bromo-quinazolinone derivatives
  作者：Mariarita Barone、Venerando Pistarà、Giuseppina Frasca、Clio Noto、Maria Scribano、Alfio Catalfo、Andrea Santagati

  DOI：10.1007/s00044-014-1311-7

  日期：2015.6

  6-Bromo-quinazolinone derivatives were prepared and evaluated for the ability to inhibit cyclooxygenase-2 (COX-2). An extensive structure-activity relationship work was carried out, thus some potent and selective COX-2 inhibitors were identified. The key compound isothiocyanate was prepared through a simple and ecological method using di-2-pyridyl thionocarbonate in substitution of the thiophosgene, a potential air pollutant. The cyclization reaction of intermediate derivatives was developed through the methods reporting by Wamhoff. The anti-inflammatory activity of the derivatives (5-12) was evaluated by determining (by Western blot) the expression of cyclooxygenase (COX)-2, of inducible NO synthase (iNOS) and of intercellular adhesion molecule-1 (ICAM-1). The biological assays showed that the derivatives 7, 9, 10, 12 act as potent inhibitors of COX-2, iNOS, and ICAM-1 expression in human keratinocytes NCTC-2544 cells. This work showed that the new derivatives could be used as a novel class of anti-inflammatory agents.