Thiaxanthonsulfoxid-(2,4-dinitro-phenylhydrazon) | 7648-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: Thiaxanthonsulfoxid-(2,4-dinitro-phenylhydrazon)
• CAS: 7648-77-3
• 化学式: C₁₉H₁₂N₄O₅S
• 分子量: 408.394
• InChiKey: SLVTWFQJLBVRRZ-VZCXRCSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127.74
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  thioxanthen-9-one 10-oxide 、 2,4-二硝基苯肼 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以90%的产率得到Thiaxanthonsulfoxid-(2,4-dinitro-phenylhydrazon)
  参考文献：
  名称：

  Design, Synthesis, and Anticancer Properties of 4,4‘-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone and Analogues

  摘要：

  4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) has recently completed a phase I clinical trial in advanced cancer with minimal toxicity, and impressive objective responses were noted. A-007 possesses three moieties that appear to have an influence on its anticancer activities: diphenylmethane, hydrazone, and dinitrophenyl. The goals of this study were to modify A-007's chemical moieties with the ultimate goal of maximizing its anticancer activity through increased planarity and introduction of functional groups. Thirty-five phenylhydrazone analogues of A-007 were synthesized and evaluated in vitro in a human primary cancer explant assay. Anticancer activities for selected analogues were also assayed for activity vs established human/murine cell lines. One-hundred-eighty-six fresh human solid tumors were used to screen for anticancer activity. Selected analogues were assayed for therapeutic indices (vs GM-CFC from bone marrow) in preparation for preclinical studies. Several polyaryl phenylhydrazones demonstrated improved cytotoxic activities by factors of 10(2)-10(3) when compared with A-007. However, the polyaryl quinone moieties of the latter analogues introduced potential toxic properties (cardiac, hematological) that do not exist with A-007.

  DOI：

  10.1021/jm0301080

文献信息

• Design, Synthesis, and Anticancer Properties of 4,4‘-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone and Analogues
  作者：Lee Roy Morgan、Kanappan Thangaraj、Blaise LeBlanc、Andrew Rodgers、Lionel T. Wolford、Catherine L. Hooper、Dominic Fan、Branko S. Jursic

  DOI：10.1021/jm0301080

  日期：2003.10.1

  4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) has recently completed a phase I clinical trial in advanced cancer with minimal toxicity, and impressive objective responses were noted. A-007 possesses three moieties that appear to have an influence on its anticancer activities: diphenylmethane, hydrazone, and dinitrophenyl. The goals of this study were to modify A-007's chemical moieties with the ultimate goal of maximizing its anticancer activity through increased planarity and introduction of functional groups. Thirty-five phenylhydrazone analogues of A-007 were synthesized and evaluated in vitro in a human primary cancer explant assay. Anticancer activities for selected analogues were also assayed for activity vs established human/murine cell lines. One-hundred-eighty-six fresh human solid tumors were used to screen for anticancer activity. Selected analogues were assayed for therapeutic indices (vs GM-CFC from bone marrow) in preparation for preclinical studies. Several polyaryl phenylhydrazones demonstrated improved cytotoxic activities by factors of 10(2)-10(3) when compared with A-007. However, the polyaryl quinone moieties of the latter analogues introduced potential toxic properties (cardiac, hematological) that do not exist with A-007.