(1,1,3-trioxo-1,2-benzothiazol-2-yl)methyl 2,6-dimethylmorpholine-4-carbodithioate

• 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: (1,1,3-trioxo-1,2-benzothiazol-2-yl)methyl 2,6-dimethylmorpholine-4-carbodithioate
• 化学式: C₁₅H₁₈N₂O₄S₃
• 分子量: 386.517
• InChiKey: MPZDUNFEMKURMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 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：
  0.47
• 拓扑面积：
  66.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-羟基甲基糖精 在 氢氧化钾 、 氯化亚砜 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 26.0h， 生成 (1,1,3-trioxo-1,2-benzothiazol-2-yl)methyl 2,6-dimethylmorpholine-4-carbodithioate
  参考文献：
  名称：

  Synthesis, antimycobacterial and antitumor activities of new (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl N,N-disubstituted dithiocarbamate/O-alkyldithiocarbonate derivatives

  摘要：

  Reaction of 2-chloromethylsaccharin with substituted potassium dithiocarbamates and substituted potassium dithiocarbonates furnished (1, 1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl NN-disubstituted dithiocarbamates (4-15) and (1, 1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyI O-alkyldithiocarbonates (16-20). The new derivatives were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Compounds 4-13, 15, and 16-20 described herein showed moderate to good inhibitory activity. In particular, seven analogs 4, 5, 6, 13, and 7, 8, and 12 exhibited excellent MIC values of 1.56 and 0.78 mu g/mL, respectively. Compounds 4, 5, 10, 12, 13, and 16 were selected and screened for antitumor activity. Among the tested compounds, 4 and 5 were found to be cytotoxic, especially against leukemia cell lines CCRF-CEM, HL-60(TB), RPMI-8226, and SR with log(10)GI(50) values lower than -6.69, and against non-small cell lung cancer NCI-H522 cell line with log(10)GI(50) values lower than -6.31. Compound 10 was cytotoxic against leukemia cell line HL-60(TB), whereas 16 displayed favorable cytotoxicity against ovarian cancer cell line OVCAR-3 with log(10)GI(50) values of -6.31 and -7.45, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.065

文献信息

• Synthesis, antimycobacterial and antitumor activities of new (1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl N,N-disubstituted dithiocarbamate/O-alkyldithiocarbonate derivatives
  作者：Özlen Güzel、Aydın Salman

  DOI：10.1016/j.bmc.2006.07.065

  日期：2006.12

  Reaction of 2-chloromethylsaccharin with substituted potassium dithiocarbamates and substituted potassium dithiocarbonates furnished (1, 1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyl NN-disubstituted dithiocarbamates (4-15) and (1, 1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)methyI O-alkyldithiocarbonates (16-20). The new derivatives were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Compounds 4-13, 15, and 16-20 described herein showed moderate to good inhibitory activity. In particular, seven analogs 4, 5, 6, 13, and 7, 8, and 12 exhibited excellent MIC values of 1.56 and 0.78 mu g/mL, respectively. Compounds 4, 5, 10, 12, 13, and 16 were selected and screened for antitumor activity. Among the tested compounds, 4 and 5 were found to be cytotoxic, especially against leukemia cell lines CCRF-CEM, HL-60(TB), RPMI-8226, and SR with log(10)GI(50) values lower than -6.69, and against non-small cell lung cancer NCI-H522 cell line with log(10)GI(50) values lower than -6.31. Compound 10 was cytotoxic against leukemia cell line HL-60(TB), whereas 16 displayed favorable cytotoxicity against ovarian cancer cell line OVCAR-3 with log(10)GI(50) values of -6.31 and -7.45, respectively. (c) 2006 Elsevier Ltd. All rights reserved.