3-benzyl-6-bromo-2H-1,3-benzoxazine-2,4(3H)-dione | 708230-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 3-benzyl-6-bromo-2H-1,3-benzoxazine-2,4(3H)-dione
• 英文别名: 3-Benzyl-6-bromo-1,3-benzoxazine-2,4-dione
• CAS: 708230-86-8
• 化学式: C₁₅H₁₀BrNO₃
• 分子量: 332.153
• InChiKey: PJHMIEVEPPGCDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-6-bromo-2H-1,3-benzoxazine-2,4(3H)-dione 在 tetraphosphorus decasulfide 作用下， 反应 0.33h， 以21%的产率得到3-benzyl-6-bromo-4-thioxo-2H-1,3-benzoxazine-2(3H)-one
  参考文献：
  名称：

  关于含硫代氧杂基团的苯并恶嗪衍生物的生物活性的注意事项

  摘要：

  合成了新的3-苄基-4-thioxo-2 H -1,3-苯并恶嗪-2（3 H）-1和3-苄基-2 H -1,3-苯并恶嗪-2,4（3 H）-二硫。测试了这些化合物对结核分枝杆菌，堪萨斯分枝杆菌和鸟分枝杆菌的体外抗分枝杆菌活性。用硫代羰基取代羰基提高了抗分枝杆菌的活性。活性最高的衍生物比异烟肼（INH）更具活性。还研究了细胞毒性和抗增殖活性。

  DOI：

  10.1016/j.ejmech.2010.02.037
• 作为产物：
  描述：

  N-benzyl-5-bromo-2-hydroxybenzamide 、 氯甲酸乙酯 在 吡啶 作用下， 反应 1.0h， 以52%的产率得到3-benzyl-6-bromo-2H-1,3-benzoxazine-2,4(3H)-dione
  参考文献：
  名称：

  3-Benzyl-2H-1,3-benzoxazine-2,4(3H)-diones, a new group of antimycobacterial compounds against potentially pathogenic strains

  摘要：

  A series of derivatives of 3-benzyl-2H-benzoxazine-2,4(3H)-dione substituted in positions 6, 7 or 8 on the benzoxazine, and in positions 3 or 4 on the benzyl moiety was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium avium and two strains of Mycobacterium kansasii. The disadvantage of the compounds is in their low solubility in water. The antimycobacterial activity of N-benzylsalicylamides correlates with that of 3-benzyl-2H-1,3-benzoxazin-2,4(3H)-diones and depends on the partition coefficients and electronic indexes.

  DOI：

  10.1016/j.farmac.2003.07.004

文献信息

• 3-Benzyl-2H-1,3-benzoxazine-2,4(3H)-diones, a new group of antimycobacterial compounds against potentially pathogenic strains
  作者：Karel Waisser、Milan Peřina、Jiřı́ Kuneš、Vera Klimešová、Jarmila Kaustová

  DOI：10.1016/j.farmac.2003.07.004

  日期：2003.11

  A series of derivatives of 3-benzyl-2H-benzoxazine-2,4(3H)-dione substituted in positions 6, 7 or 8 on the benzoxazine, and in positions 3 or 4 on the benzyl moiety was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium avium and two strains of Mycobacterium kansasii. The disadvantage of the compounds is in their low solubility in water. The antimycobacterial activity of N-benzylsalicylamides correlates with that of 3-benzyl-2H-1,3-benzoxazin-2,4(3H)-diones and depends on the partition coefficients and electronic indexes.
• A note to the biological activity of benzoxazine derivatives containing the thioxo group
  作者：Karel Waisser、Eva Petrlíková、Milan Peřina、Věra Klimešová、Jiří Kuneš、Karel Palát、Jarmila Kaustová、Hans-Martin Dahse、Ute Möllmann

  DOI：10.1016/j.ejmech.2010.02.037

  日期：2010.7

  synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. The replacement of the carbonyl group by the thiocarbonyl group increased the antimycobacterial activity. The most active derivatives were more active than isonicotinhydrazide (INH). The cytotoxicity and the antiproliferative activity were studied as

  合成了新的3-苄基-4-thioxo-2 H -1,3-苯并恶嗪-2（3 H）-1和3-苄基-2 H -1,3-苯并恶嗪-2,4（3 H）-二硫。测试了这些化合物对结核分枝杆菌，堪萨斯分枝杆菌和鸟分枝杆菌的体外抗分枝杆菌活性。用硫代羰基取代羰基提高了抗分枝杆菌的活性。活性最高的衍生物比异烟肼（INH）更具活性。还研究了细胞毒性和抗增殖活性。