6-chloro-3-thioxo-2,3-dihydro-1,4,2-benzodithiazine 1,1-dioxide | 642442-13-5

• 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-thioxo-2,3-dihydro-1,4,2-benzodithiazine 1,1-dioxide
• 英文别名: 6-Chloro-3-sulfanylidene-2,3-dihydro-1H-1lambda~6~,4,2-benzodithiazine-1,1-dione；6-chloro-1,1-dioxo-1λ6,4,2-benzodithiazine-3-thione
• CAS: 642442-13-5
• 化学式: C₇H₄ClNO₂S₃
• 分子量: 265.765
• InChiKey: FEFDYTPHKAOMEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-3-thioxo-2,3-dihydro-1,4,2-benzodithiazine 1,1-dioxide 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 生成 4-dimethylaminopyridinium 4-chloro-N-(6-chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)benzenesulfonamidate
  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, 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.