2,4-diamino-8-chloro-10-(4-methoxyphenyl)-10H-pyrimido[5,4-b][1,4]benzothiazine 5,5-dioxide | 1147373-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2,4-diamino-8-chloro-10-(4-methoxyphenyl)-10H-pyrimido[5,4-b][1,4]benzothiazine 5,5-dioxide
• 英文别名: 8-Chloro-10-(4-methoxyphenyl)-5,5-dioxopyrimido[5,4-b][1,4]benzothiazine-2,4-diamine
• CAS: 1147373-40-7
• 化学式: C₁₇H₁₄ClN₅O₃S
• 分子量: 403.849
• InChiKey: LBKWFAXCBDHNPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  盐酸胍 、 6-chloro-4-(4-methoxyphenyl)-3-methylthio-1,4-benzothiazine-2-carbonitrile 1,1-dioxide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以68%的产率得到2,4-diamino-8-chloro-10-(4-methoxyphenyl)-10H-pyrimido[5,4-b][1,4]benzothiazine 5,5-dioxide
  参考文献：
  名称：

  Synthesis and antimalarial activity of pyrazolo and pyrimido benzothiazine dioxide derivatives

  摘要：

  A series of phenylsubstituted pyrazolo and pyrimido benzothiazine dioxide derivatives were synthesized and investigated for their abilities to inhibit beta-hematin formation, hemoglobin hydrolysis and in vivo for their antimalarial efficacy in rodent Plasmodium berghei. Compounds 3-amino-7-chloro-9-(2'-methylpheyl)-1,9-dihydro-pyrazolo-[4,3-b]benzothiazine 4,4-dioxide 2b and 2,4-diamino-8-chloro-10H-phenyl-pyrimido-[5,4-b]benzothiazine 5,5-dioxide 3a were the most promising as inhibitors of hemoglobin hydrolysis, however, their effect as inhibitors of beta-hematin formation was marginal, except for compound 3-amino-7-chloro-9-(3'-chlorophenyl)-1,9dihydro-pyrazolo-[4,3-b]benzothiazine 4,4-dioxide 2g. The most active compound to emerge from the in vitro and in vivo murine studies was 2b, suggesting an antimalarial activity via inhibition of hemoglobin hydrolysis, however, not as efficient as chloroquine. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2008.08.005

文献信息

• Synthesis and antimalarial activity of pyrazolo and pyrimido benzothiazine dioxide derivatives
  作者：Arthur Barazarte、Gricela Lobo、Neira Gamboa、Juan R. Rodrigues、Mario V. Capparelli、Ángel Álvarez-Larena、Simón E. López、Jaime E. Charris

  DOI：10.1016/j.ejmech.2008.08.005

  日期：2009.3

  A series of phenylsubstituted pyrazolo and pyrimido benzothiazine dioxide derivatives were synthesized and investigated for their abilities to inhibit beta-hematin formation, hemoglobin hydrolysis and in vivo for their antimalarial efficacy in rodent Plasmodium berghei. Compounds 3-amino-7-chloro-9-(2'-methylpheyl)-1,9-dihydro-pyrazolo-[4,3-b]benzothiazine 4,4-dioxide 2b and 2,4-diamino-8-chloro-10H-phenyl-pyrimido-[5,4-b]benzothiazine 5,5-dioxide 3a were the most promising as inhibitors of hemoglobin hydrolysis, however, their effect as inhibitors of beta-hematin formation was marginal, except for compound 3-amino-7-chloro-9-(3'-chlorophenyl)-1,9dihydro-pyrazolo-[4,3-b]benzothiazine 4,4-dioxide 2g. The most active compound to emerge from the in vitro and in vivo murine studies was 2b, suggesting an antimalarial activity via inhibition of hemoglobin hydrolysis, however, not as efficient as chloroquine. (C) 2008 Published by Elsevier Masson SAS.