methyleneorthosulfonictetrakis(8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylic) anhydride | 393843-05-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyleneorthosulfonictetrakis(8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylic) anhydride
• 英文别名: [Tris[(8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carbonyl)oxy]-methylidene-lambda6-sulfanyl] 8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylate；[tris[(8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carbonyl)oxy]-methylidene-λ6-sulfanyl] 8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylate
• CAS: 393843-05-5
• 化学式: C₄₁H₁₈Cl₄N₈O₁₆S₉
• 分子量: 1309.04
• InChiKey: IKABPSPYAGXEDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  78
• 可旋转键数：
  12
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  449
• 氢给体数：
  0
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  亚氨基芪 、 methyleneorthosulfonictetrakis(8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylic) anhydride 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以89%的产率得到Benzo[b][1]benzazepin-11-yl-(8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazin-7-yl)methanone
  参考文献：
  名称：

  A New Type of Mixed Anhydride and Its Applications to the Synthesis of 7-Substituted 8-Chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazines with in Vitro Antitumor Activity

  摘要：

  A new series of 8-chloro-5,5-dioxoimidazo[1,2-b] [1,4,2]benzodithiazine derivatives 8-25 with heteroaryloxycarbonyl or heteroarylcarbamoyl substituents at position 7 have been synthesized as potential antitumor agents. In this procedure a novel type of mixed anhydride 7 was prepared from 8-chloro-5,5-dioxoimidazo[1,2-b] [1,4,2]benzodithiazine-7-carboxylic acid 6 and methanesulfonyl chloride, which in turn was condensed either with heteroarylamines or heteroarylhydroxy compounds. All the compounds prepared were screened at the National Cancer Institute (NCI) for their activities against a panel of 60 tumor cell lines, and relationships between structure and antitumor activity in vitro are discussed. The amides 8, 10, 12, 13, 21, and ester 25 were inactive, whereas the other compounds exhibited rather moderate activity against one or more human tumor cell lines. The prominent compound with remarkable activity (log GI(50) < -8) and selectivity for the leukemia HL-60(TB) cell line was 2-methyl-8-quinolyl 8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylate 24.

  DOI：

  10.1021/jm010953n
• 作为产物：
  描述：

  6-Chloro-3-(2,2-dimethoxy-ethylamino)-1,1-dioxo-1H-1λ6-benzo[1,4,2]dithiazine-7-carboxylic acid methyl ester 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.5h， 生成 methyleneorthosulfonictetrakis(8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylic) anhydride
  参考文献：
  名称：

  A New Type of Mixed Anhydride and Its Applications to the Synthesis of 7-Substituted 8-Chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazines with in Vitro Antitumor Activity

  摘要：

  A new series of 8-chloro-5,5-dioxoimidazo[1,2-b] [1,4,2]benzodithiazine derivatives 8-25 with heteroaryloxycarbonyl or heteroarylcarbamoyl substituents at position 7 have been synthesized as potential antitumor agents. In this procedure a novel type of mixed anhydride 7 was prepared from 8-chloro-5,5-dioxoimidazo[1,2-b] [1,4,2]benzodithiazine-7-carboxylic acid 6 and methanesulfonyl chloride, which in turn was condensed either with heteroarylamines or heteroarylhydroxy compounds. All the compounds prepared were screened at the National Cancer Institute (NCI) for their activities against a panel of 60 tumor cell lines, and relationships between structure and antitumor activity in vitro are discussed. The amides 8, 10, 12, 13, 21, and ester 25 were inactive, whereas the other compounds exhibited rather moderate activity against one or more human tumor cell lines. The prominent compound with remarkable activity (log GI(50) < -8) and selectivity for the leukemia HL-60(TB) cell line was 2-methyl-8-quinolyl 8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylate 24.

  DOI：

  10.1021/jm010953n

文献信息

• A New Type of Mixed Anhydride and Its Applications to the Synthesis of 7-Substituted 8-Chloro-5,5-dioxoimidazo[1,2-<i>b</i>][1,4,2]benzodithiazines with in Vitro Antitumor Activity
  作者：Zdzisław Brzozowski、Franciszek Sa̧czewski

  DOI：10.1021/jm010953n

  日期：2002.1.1

  A new series of 8-chloro-5,5-dioxoimidazo[1,2-b] [1,4,2]benzodithiazine derivatives 8-25 with heteroaryloxycarbonyl or heteroarylcarbamoyl substituents at position 7 have been synthesized as potential antitumor agents. In this procedure a novel type of mixed anhydride 7 was prepared from 8-chloro-5,5-dioxoimidazo[1,2-b] [1,4,2]benzodithiazine-7-carboxylic acid 6 and methanesulfonyl chloride, which in turn was condensed either with heteroarylamines or heteroarylhydroxy compounds. All the compounds prepared were screened at the National Cancer Institute (NCI) for their activities against a panel of 60 tumor cell lines, and relationships between structure and antitumor activity in vitro are discussed. The amides 8, 10, 12, 13, 21, and ester 25 were inactive, whereas the other compounds exhibited rather moderate activity against one or more human tumor cell lines. The prominent compound with remarkable activity (log GI(50) < -8) and selectivity for the leukemia HL-60(TB) cell line was 2-methyl-8-quinolyl 8-chloro-5,5-dioxoimidazo[1,2-b][1,4,2]benzodithiazine-7-carboxylate 24.