3-(4-Bromo-phenyl)-6-chloro-4-thioxo-3,4-dihydro-benzo[e][1,3]oxazin-2-one

• 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-(4-Bromo-phenyl)-6-chloro-4-thioxo-3,4-dihydro-benzo[e][1,3]oxazin-2-one
• 英文别名: 3-(4-bromophenyl)-6-chloro-4-sulfanylidene-1,3-benzoxazin-2-one
• 化学式: C₁₄H₇BrClNO₂S
• 分子量: 368.638
• InChiKey: VPHDUAGOBSAMFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-溴苯基)-5-氯-2-羟基苯甲酰胺 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 1.33h， 生成 3-(4-Bromo-phenyl)-6-chloro-4-thioxo-3,4-dihydro-benzo[e][1,3]oxazin-2-one
  参考文献：
  名称：

  New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 -1,3-benzoxazine-2(3 )-ones and 6-chloro-3-phenyl-2 -1,3-benzoxazine-2,4(3 )-dithiones

  摘要：

  A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4 and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compounds 2c-e, 3 and 4 exhibited in vitro activity against Mycobacterium tuberculosis, M. kansasii (two strains) and M. avium better than or comparable to that of isoniazid. Replacement of the oxo group by a thioxo group at position 4 led to improvement in activity against M. tuberculosis and M. kansasii. The Free-Wilson method and procedure developed by the authors were used to analyse the structure-activity and structure-antimycobacterial profile relationships, respectively. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00174-4

文献信息

• New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 -1,3-benzoxazine-2(3 )-ones and 6-chloro-3-phenyl-2 -1,3-benzoxazine-2,4(3 )-dithiones
  作者：Karel Waisser、Jiří Gregor、Lenka Kubicová、Věra Klimešová、Jiří Kuneš、Miloš Macháček、Jarmila Kaustová

  DOI：10.1016/s0223-5234(00)00174-4

  日期：2000.8

  A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4 and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compounds 2c-e, 3 and 4 exhibited in vitro activity against Mycobacterium tuberculosis, M. kansasii (two strains) and M. avium better than or comparable to that of isoniazid. Replacement of the oxo group by a thioxo group at position 4 led to improvement in activity against M. tuberculosis and M. kansasii. The Free-Wilson method and procedure developed by the authors were used to analyse the structure-activity and structure-antimycobacterial profile relationships, respectively. (C) 2000 Editions scientifiques et medicales Elsevier SAS.