6-chloro-3-methylthio-7-(phenylcarbamoyl)-1,1-dioxo-1,4,2-benzodithiazine | 189126-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-chloro-3-methylthio-7-(phenylcarbamoyl)-1,1-dioxo-1,4,2-benzodithiazine
• CAS: 189126-95-2
• 化学式: C₁₅H₁₁ClN₂O₃S₃
• 分子量: 398.915
• InChiKey: WYSCNTLHDCUQQY-UHFFFAOYSA-N

物化性质

• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.6
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-chloro-3-methylthio-7-(phenylcarbamoyl)-1,1-dioxo-1,4,2-benzodithiazine 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 2-chloro-4-mercapto-5-(3-oxo-[1,2,4]triazinane-4-sulfonyl)-N-phenyl-benzamide
  参考文献：
  名称：

  Pomarnacka, Elzbieta, Acta poloniae pharmaceutica, 1998, vol. 55, # 6, p. 481 - 486

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 、 chlorek kwasu 6-chloro-3-metylotio-1,1-diokso-1,4,2-benzoditiazyno-7-karboksylowego 以 苯 为溶剂， 反应 24.0h， 以87%的产率得到6-chloro-3-methylthio-7-(phenylcarbamoyl)-1,1-dioxo-1,4,2-benzodithiazine
  参考文献：
  名称：

  Pomarnacka, Elzbieta, Acta poloniae pharmaceutica, 1996, vol. 53, # 5, p. 373 - 378

  摘要：

  DOI：

文献信息

• Novel 5-Substituted 2-(Aylmethylthio)-4-chloro-N-(5-aryl-1,2,4-triazin-3-yl)benzenesulfonamides: Synthesis, Molecular Structure, Anticancer Activity, Apoptosis-Inducing Activity and Metabolic Stability
  作者：Beata Żołnowska、Jarosław Sławiński、Aneta Pogorzelska、Krzysztof Szafrański、Anna Kawiak、Grzegorz Stasiłojć、Mariusz Belka、Szymon Ulenberg、Tomasz Bączek、Jarosław Chojnacki

  DOI：10.3390/molecules21060808

  日期：——

  A series of novel 5-substituted 2-(arylmethylthio)-4-chloro-N-(5-aryl-1,2,4-triazin-3-yl) benzenesulfonamide derivatives 27–60 have been synthesized by the reaction of aminoguanidines with an appropriate phenylglyoxal hydrate in glacial acetic acid. A majority of the compounds showed cytotoxic activity toward the human cancer cell lines HCT-116, HeLa and MCF-7, with IC50 values below 100 μM. It was

  通过氨基胍与 2-(芳甲硫基)-4-氯-N-(5-芳基-1,2,4-三嗪-3-基)苯磺酰胺衍生物 27-60 的反应合成了一系列新型 5-取代的 2-(芳甲硫基)-4-氯-N-(5-芳基-1,2,4-三嗪-3-基)苯磺酰胺衍生物。一种合适的苯乙二醛水合物在冰醋酸中。大多数化合物对人类癌细胞系 HCT-116、HeLa 和 MCF-7 显示出细胞毒活性，IC50 值低于 100 μM。发现对于类似物 36-38，萘基部分对抗癌活性有显着贡献。磷脂酰丝氨酸易位以及线粒体膜电位和细胞周期的细胞计量分析显示，最活跃的化合物 37（HCT-116 和 HeLa）和 46（MCF-7）通过增加凋亡细胞的数量来抑制细胞增殖。凋亡样，在用 37 和 46 处理后，还注意到细胞系形态的剂量依赖性变化。此外，三嗪 37 和 46 在 HCT-116、HeLa 和 MCF-7 细胞系中诱导了半胱天冬酶活性。在合并的人肝微粒体和
• Synthesis and in vitro anticancer and anti-HIV evaluation of new 2-mercaptobenzenesulfonamides
  作者：Elżbieta Pomarnacka、Anita Kornicka

  DOI：10.1016/s0014-827x(01)01095-3

  日期：2001.8

  The reactions of 6-chloro-3-methylthio-1,4,2-benzodithiazine 1,1-dioxide derivatives with appropriate diamines were investigated. Depending on the reaction conditions 2-mercaptobenzenesulfonamide derivatives or their oxidation product disulfides were obtained. All the compounds were tested at the US National Cancer Institute (Bethesda) for their in vitro anticancer and anti-HIV activities. The highest sensibility against leukemia cell lines was found for bis[2-(6-chloro-4-phenyl-3,4-dihydroquinazolin-2-yl)aminosulfonyl-5-chloro-4-(4-R-2 -phenylcarbamoyl)phenyl]disulfides (R-2 = H or Cl). The results of anti-HIV tests displayed moderate activity of N-(pirydo[3,2-d]imidazol-2-yl)-2-mercaptobenzenesulfonamide. (C) 2001 Elsevier Science S.A. All rights reserved.
• Brzozowski; Slawinski, Polish Journal of Chemistry, 2007, vol. 81, # 8, p. 1419 - 1426
  作者：Brzozowski、Slawinski

  DOI：——

  日期：——
• Pomarnacka, Polish Journal of Chemistry, 2007, vol. 81, # 3, p. 345 - 352
  作者：Pomarnacka

  DOI：——

  日期：——
• Synthesis of novel 3-amino-2-(4-chloro-2-mercaptobenzenesulfonyl)-guanidine derivatives as potential antitumor agents
  作者：Zdzisław Brzozowski、Franciszek Sączewski、Jarosław Sławiński

  DOI：10.1016/j.ejmech.2007.01.020

  日期：2007.9

  Novel 3-amino-2-(4-chloro-2-mercaptobenzenesulfonyl)guanidine derivatives have been synthesized as potential anticancer agents. The in vitro antitumor activity of these compounds has been evaluated in the US National Cancer Institute (NCI), and relationships between structure and antitumor activity are discussed. The prominent compound was 1-allyl-2-[4-chloro-5-(4-chlorophenylcarbamoyl)-2-methylthiobenzenesulfonyl]-3-(5-nitrofurfurylideneamino)guanidine (8) with remarkable activity against 21 human tumor cell lines representing leukemia, lung, colon, melanoma, ovarian, renal, prostate and breast (GI(50) = 0.3-3.0 mu M), and selectivity toward leukemia RPMI-8226 cell line (GI(50) = 0.3 VM, TGI = 1.4 mu M). (c) 2007 Elsevier Masson SAS. All rights reserved.