1,4-Bis((2-(dimethylamino)ethyl)amino)-6-methyl-9,10-anthracenedione | 70945-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-Bis((2-(dimethylamino)ethyl)amino)-6-methyl-9,10-anthracenedione
• 英文别名: 1,4-bis[2-(dimethylamino)ethylamino]-6-methylanthracene-9,10-dione
• CAS: 70945-54-9
• 化学式: C₂₃H₃₀N₄O₂
• 分子量: 394.517
• InChiKey: PSCSHWDJXRUYPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲基苯酐 在 三氯化铝 、 sodium chloride 作用下， 生成 1,4-Bis((2-(dimethylamino)ethyl)amino)-6-methyl-9,10-anthracenedione
  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：——
• Antitumor agents. 1. 1,4-Bis[(aminoalkyl)amino]-9,10-anthracenediones
  作者：K. C. Murdock、R. G. Child、P. F. Fabio、Robert D. Angier、Roslyn E. Wallace、Frederick E. Durr、R. V. Citarella

  DOI：10.1021/jm00195a002

  日期：1979.9

  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.