6-chloro-3-methylthio-1,4,2-benzodithiazine 1,1-dioxide | 113922-99-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-chloro-3-methylthio-1,4,2-benzodithiazine 1,1-dioxide
• 英文别名: 6-Chloro-3-(methylsulfanyl)-1H-1lambda~6~,4,2-benzodithiazine-1,1-dione；6-chloro-3-methylsulfanyl-1λ6,4,2-benzodithiazine 1,1-dioxide
• CAS: 113922-99-9
• 化学式: C₈H₆ClNO₂S₃
• 分子量: 279.792
• InChiKey: QBRVBKMQNJQVGK-UHFFFAOYSA-N

物化性质

• 熔点：
  191.5-192.5 °C
• 沸点：
  481.7±47.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-3-methylthio-1,4,2-benzodithiazine 1,1-dioxide 在 吡啶 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 4-chloro-2-mercapto-N-(1,2,4-triazolo<4,3-a>quinol-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Brzozowski, ZdzislLaw, Acta poloniae pharmaceutica, 1998, vol. 55, # 6, p. 473 - 480

  摘要：

  DOI：
• 作为产物：
  描述：

  硫酸二甲酯 、 6-chloro-3-thioxo-2,3-dihydro-1,4,2-benzodithiazine 1,1-dioxide 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以91%的产率得到6-chloro-3-methylthio-1,4,2-benzodithiazine 1,1-dioxide
  参考文献：
  名称：

  Synthesis, structural characterization and In vitro antitumor activity of novel 6-Chloro-1,1-dioxo-1,4,2-benzodithiazie derivatives

  摘要：

  A series of nonconventional aminium N-(6-chloro-7-R-1,1-dioxo- 1,4,2-benzodithiazin-3-yl)arylsulfonamidates 7-15 have been synthesized by the reactions of 6-chloro-7-R-3-methylthio-1,4,2-benzodithiazine 1,1-dioxides with 4-dimethylaminopyridine or Et3N and some arylsulfonamides. The free N-(6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazin-3-yl)benzenesulfonamides 16-18 were obtained by treatment of their aminium salts with H2SO4 in boiling acetic acid. The in vitro antitumor activity of the compounds 9, 11-14 and 16-18 has been tested in the antitumor screening of the National Cancer Institute (NCI), and relationships between structure and antitumor activity are discussed. 4-Dimethylaminopyridinium 4-chloro-N-(6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazin-3-yl)benzenesulfonamidate 9 is the prominent of the compounds due to its remarkable activity (log GI(50) < -8.00. log TGI = -5.50) and selectivity for the leukemia SR cell line. For that reason experimental and theoretical analysis of the geometric and electronic properties of 9 was carried out. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00345-6

文献信息

• Synthesis and anti-HIV-1 activity of a novel series of 1,4,2-benzodithiazine-dioxides
  作者：Zdzisław Brzozowski、Franciszek Sączewski、Nouri Neamati

  DOI：10.1016/j.bmcl.2006.07.089

  日期：2006.10

  we discovered a series of novel benzodithiazines-dioxides with both antiviral and anticancer activities. In order to design compounds with distinct antiviral properties, we prepared new compounds with modifications on the imidazole and pyrimidine rings. Herein, we present the synthesis and antiviral activity of 8-chloro-2,3-dihydroimidazo[1,2-b][1,4,2]benzodithiazine 5,5-dioxides (22, 23, 30, and 31)

  以前，我们发现了一系列具有抗病毒和抗癌活性的新型二苯并噻嗪类二氧化物。为了设计具有独特抗病毒特性的化合物，我们制备了在咪唑和嘧啶环上经过修饰的新化合物。在这里，我们介绍了8-氯-2,3-二氢咪唑并[1,2-b] [1,4,2]苯并噻二嗪5,5-二氧化物（22、23、30和31）的合成和抗病毒活性，以及9-氯-2,3,4-三氢嘧啶基[1,2-b] [1,4,2]苯并噻二嗪6,6-二氧化物（14、24、25和27）。我们成功地鉴定出具有显着抗HIV-1活性（EC（50）= 0.09microM）的先导化合物。这些化合物显示出最小的细胞毒性，因此适用于抗病毒开发。
• Synthesis, structural characterization and in vitro antitumor activity of 4-dimethylaminopyridinium (6-chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)methanides
  作者：Zdzislaw Brzozowski、Franciszek Sączewski、Maria Gdaniec

  DOI：10.1016/j.ejmech.2003.09.007

  日期：2003.11

  Previously, We have described a novel series of low molecular weight cancer-specific antitumor agents with aminium N-(1,1-dioxo-1,4,2-benzodithiazin-3-yl)arylsulfonamidate structure. In an attempt to determine some of the structural features that account for the cytotoxic activity of such aminium salts, a novel series of 4-dimethylaminopyridinium (1,1-dioxo-1,4,2-benzodithiazin-3-yl)methanides (6-19) has been synthesized by the reactions of 3-methylthio-1,4,2-benzodithiazine1,1-dioxides with 4-DMAP and some active methylene compounds. The in vitro antitumor activity of these compounds has been tested in the National Cancer Institute (NCI), and relationships between structure and antitumor activity are discussed. Among the aminium salts 4-dimethylamino-pyridinium 4-chlorobenzoyl cyano (6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazin-3-yl)methanide (9) was superior to other pyridinium salts in terms of both remarkable activity (log GI(50) and log TGI < -8.00) and high selectivity for the lung HOP-92 and melanoma UACC-257 cell lines. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Synthesis and biological activity of new 2-amino-8-chloro-5,5-dioxo[1,2,4]triazolo[2,3-b][1,4,2]benzodithiazines
  作者：Elżbieta Pomarnacka、Patrick J. Bednarski、Przemysław Reszka、Ewa Dziemidowicz-Borys、Andrzej Bieńczak、Władysław Werel、Rafał Hałasa

  DOI：10.1016/j.ejmech.2005.11.009

  日期：2006.5

  Two series of 1-(6-chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)-4-arylsemicarbazides 6-17 and 2-arylamino-8-chloro-5,5-dioxo[1,2,4]triazolo [2,3-b][1,4,2]benzodithiazines 18-26 were prepared in order to evaluate their biological activity. Compounds 6 and 18-26 were tested for their in vitro cytotoxic potency against 12 human cancer cell lines. The compounds 6 and 19 were inactive, whereas triazolobenzodithiazines 18, 20-26 possess tumor growth inhibitory properties. The prominent methyl 8-chloro-2-(4-chlorophenylamino)-5,5-dioxo[1,2,4]triazolo[2,3-b][1,4,2]benzodithiazine-7-carboxylate (21) exhibited potency higher or comparable to cisplatin. Moreover, compounds 6, 9 19 and 23-25 with structure similar to other chemotherapeutic agents were tested for their antibacterial activity and exhibited MIC and MBC against Staphylococcus aureus (3.9-31.5 mu g ml). (c) 2006 Elsevier SAS. All rights reserved.
• Brzozowski, ZdzislLaw, Acta poloniae pharmaceutica, 1998, vol. 55, # 6, p. 473 - 480
  作者：Brzozowski, ZdzislLaw

  DOI：——

  日期：——
• Synthesis, structural characterization and In vitro antitumor activity of novel 6-Chloro-1,1-dioxo-1,4,2-benzodithiazie derivatives
  作者：Zdzislaw Brzozowski、Franciszek Sa̧czewski、Maria Gdaniec

  DOI：10.1016/s0968-0896(03)00345-6

  日期：2003.8

  A series of nonconventional aminium N-(6-chloro-7-R-1,1-dioxo- 1,4,2-benzodithiazin-3-yl)arylsulfonamidates 7-15 have been synthesized by the reactions of 6-chloro-7-R-3-methylthio-1,4,2-benzodithiazine 1,1-dioxides with 4-dimethylaminopyridine or Et3N and some arylsulfonamides. The free N-(6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazin-3-yl)benzenesulfonamides 16-18 were obtained by treatment of their aminium salts with H2SO4 in boiling acetic acid. The in vitro antitumor activity of the compounds 9, 11-14 and 16-18 has been tested in the antitumor screening of the National Cancer Institute (NCI), and relationships between structure and antitumor activity are discussed. 4-Dimethylaminopyridinium 4-chloro-N-(6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazin-3-yl)benzenesulfonamidate 9 is the prominent of the compounds due to its remarkable activity (log GI(50) < -8.00. log TGI = -5.50) and selectivity for the leukemia SR cell line. For that reason experimental and theoretical analysis of the geometric and electronic properties of 9 was carried out. (C) 2003 Elsevier Ltd. All rights reserved.