| 71065-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 71065-58-2
• 化学式: C₁₄H₈Cl₂O₄
• 分子量: 311.121
• InChiKey: AJCKNOAPFCCOMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  、 N,N-二甲基乙二胺 生成 9,10-Anthracenedione, 6,7-dichloro-1,4-bis((2-(dimethylamino)ethyl)amino)-
  参考文献：
  名称：

  Antitumor agents. 1. 1,4-Bis[(aminoalkyl)amino]-9,10-anthracenediones

  摘要：

  The condensation of alkylenediamines with quinizarin or with 2,3-dihydro-1,4,5,8-tetrahydroxy-9,10-anthracenedione, followed by oxidation, gave 1,4-bis[aminoalkyl)amino]-9,10-anthracenediones. Some of these compounds and their 2,3-dihydro derivatives were markedly active against both leukemias and solid tumors in mice. Activity was maximal with 5,8-dihydroxylation and 1,4-bis[(2-aminoethyl)amino] substitution, in which the terminal nitrogen atoms were either unsubstituted (compound 50) or carried 2-hydroxyethyl groups (compound 40), indicating the importance of hydrophilicity. Against B-16 melanoma, 50 gave greater than 433% increase in median life span (ILS) with 7/10 80-day survivors. Against P-388 leukemia, 40 gave greater than 500% ILS with 4/5.60-day survivors; its efficacy and therapeutic index equaled or surpassed those of adriamycin, cyclophosphamide, daunorubicin, methotrexate, or 5-fluorouracil. Against L-1210 leukemia, B-16 melanoma, and colon tumor 26, 40 was generally as effective or more effective than adriamycin and is now undergoing preclinical toxicological evaluation.

  DOI：

  10.1021/jm00195a002
• 作为产物：
  描述：

  6,7-二氯-1,4-二羟基蒽醌 在 溶剂黄146 、 锌 作用下， 生成
  参考文献：
  名称：

  Antitumor agents. 1. 1,4-Bis[(aminoalkyl)amino]-9,10-anthracenediones

  摘要：

  The condensation of alkylenediamines with quinizarin or with 2,3-dihydro-1,4,5,8-tetrahydroxy-9,10-anthracenedione, followed by oxidation, gave 1,4-bis[aminoalkyl)amino]-9,10-anthracenediones. Some of these compounds and their 2,3-dihydro derivatives were markedly active against both leukemias and solid tumors in mice. Activity was maximal with 5,8-dihydroxylation and 1,4-bis[(2-aminoethyl)amino] substitution, in which the terminal nitrogen atoms were either unsubstituted (compound 50) or carried 2-hydroxyethyl groups (compound 40), indicating the importance of hydrophilicity. Against B-16 melanoma, 50 gave greater than 433% increase in median life span (ILS) with 7/10 80-day survivors. Against P-388 leukemia, 40 gave greater than 500% ILS with 4/5.60-day survivors; its efficacy and therapeutic index equaled or surpassed those of adriamycin, cyclophosphamide, daunorubicin, methotrexate, or 5-fluorouracil. Against L-1210 leukemia, B-16 melanoma, and colon tumor 26, 40 was generally as effective or more effective than adriamycin and is now undergoing preclinical toxicological evaluation.

  DOI：

  10.1021/jm00195a002

文献信息

• MURDOCK K. C.; CHILD R. G.; FABIO P. F.; ANGIER R. B.; WALLACE R. E.; DUR+, J. MED. CHEM., 1979, 22, NO 9, 1024-1030
  作者：MURDOCK K. C.、 CHILD R. G.、 FABIO P. F.、 ANGIER R. B.、 WALLACE R. E.、 DUR+

  DOI：——

  日期：——