2,4-dihydroxybenzophenone 2,4-dinitrophenylhydrazone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dihydroxybenzophenone 2,4-dinitrophenylhydrazone
• 英文别名: 4-{[(2,4-dinitrophenyl)hydrazono]phenylmethyl}benzene-1,3-diol；2,4-dihydroxy-benzophenone-(2,4-dinitro-phenylhydrazone)；2,4-Dihydroxy-benzophenon-(2,4-dinitro-phenylhydrazon)；4-[(E)-N-(2,4-dinitroanilino)-C-phenylcarbonimidoyl]benzene-1,3-diol
• 化学式: C₁₉H₁₄N₄O₆
• 分子量: 394.343
• InChiKey: MLHGXLBSSVHOAR-XUTLUUPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  157
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,4-二羟二苯甲酮 、 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2,4-dihydroxybenzophenone 2,4-dinitrophenylhydrazone
  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.
• 2,4-Dinitrophenylhydrazones of 2,4-dihydroxybenzaldehyde, 2,4-dihydroxyacetophenone and 2,4-dihydroxybenzophenone
  作者：Russell G. Baughman、Kenneth L. Martin、Rajendra K. Singh、James O. Stoffer

  DOI：10.1107/s0108270103027197

  日期：2004.2.15

  In 2,4-dihydroxybenzaldehyde 2,4-dinitrophenylhydrazone N,N-dimethylformamide solvate or 4-[(2,4-dinitrophenyl)-hydrazonomethyl]benzene-1,3-diol N,N-dimethylformamide solvate}, C13H10N4O6.C3H7NO, (X), 2,4-dihydroxyacetophenone 2,4-dinitrophenylhydrazone N,N-dimethylformamide solvate (or 4-1-[(2,4-dinitrophenyl)hydrazono]ethyl}-benzene-1,3-diol N,N-dimethylformamide solvate), C14H12N4O6.C3H7NO, (XI), and 2,4-dihydroxybenzophenone 2,4-dinitrophenylhydrazone N,N-dimethylacetamide solvate (or 4-[(2,4-dinitrophenyl)hydrazono]phenylmethyl}benzene-1,3-diol N,N-dimethylacetamide solvate), C19H14N4O6.C4H9NO, (XII), the molecules all lack a center of symmetry, crystallize in centrosymmetric space groups and have been observed to exhibit non-linear optical activity. In each case, the hydrazone skeleton is fairly planar, facilitated by the presence of two intramolecular hydrogen bonds and some partial N-N double-bond character. Each molecule is hydrogen bonded to one solvent molecule.