7-Chloro-4-(3-methoxy-phenyl)-3-methylsulfanyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,4]thiazine-2-carbonitrile | 853688-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 7-Chloro-4-(3-methoxy-phenyl)-3-methylsulfanyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,4]thiazine-2-carbonitrile
• CAS: 853688-34-3
• 化学式: C₁₇H₁₃ClN₂O₃S₂
• 分子量: 392.887
• InChiKey: OEKNCUFLARSRTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  559.0±50.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.4
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  7-Chloro-4-(3-methoxy-phenyl)-3-methylsulfanyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,4]thiazine-2-carbonitrile 在 吡啶 、 一水合肼 作用下， 反应 5.0h， 以42%的产率得到3-amino-6-chloro-9-(3-methoxyphenyl)-1,9-dihydropyrazolo[4,3-b][1,4]benzothiazine 4,4-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
• 作为产物：
  描述：

  (Z)-2-(2,5-Dichloro-benzenesulfonyl)-3-(3-methoxy-phenylamino)-3-methylsulfanyl-acrylonitrile 在 potassium carbonate 作用下， 反应 0.15h， 以87%的产率得到7-Chloro-4-(3-methoxy-phenyl)-3-methylsulfanyl-1,1-dioxo-1,4-dihydro-1λ⁶-benzo[1,4]thiazine-2-carbonitrile
  参考文献：
  名称：

  Charris, Jaime; Barazarte, Arthur; Dominguez, Jose, Journal of Chemical Research, 2005, # 1, p. 27 - 28

  摘要：

  DOI：

文献信息

• Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs
  作者：Arthur Barazarte、José Camacho、José Domínguez、Gricela Lobo、Neira Gamboa、Juan Rodrigues、Mario V. Capparelli、Ángel Álvarez-Larena、Sebastian Andujar、Daniel Enriz

  DOI：10.1016/j.bmc.2008.02.011

  日期：2008.4.1

  An improved procedure for the synthesis of 3-amino-9-arylsubstituted-thieno[3,2-b]benzothiazine S,S-dioxide 2-decarboxylated is reported. Thieno-[3,2-b]benzothiazine S,S-dioxide derivatives were investigated for their abilities to inhibit beta-hematin formation, hemoglobin hydrolysis and in vivo for their efficacy in rodent Plasmodium berghei. Compounds 5j-o were the most promising as inhibitors of

  报道了一种改进的合成3-氨基-9-芳基取代的噻吩并[3，2-b]苯并噻嗪S，S-二氧化物2-脱羧的方法。研究了噻吩并[[3,2-b]苯并噻嗪S，S-二氧化物衍生物具有抑制β-血红素形成，血红蛋白水解的能力，并具有体内杀灭鼠伯氏疟原虫的功效。化合物5j-o是最有希望的血红蛋白水解抑制剂，但是，这些化合物不如氯喹有效。在该系列中进行了结构-活性关系（SAR）研究。我们的结果使我们能够确定产生生物学反应的最小结构要求。