1,4-Bis[(2-dimethylaminoethyl)amino]-5,6-dihydroxy-anthraquinone | 69837-16-7

• 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-dimethylaminoethyl)amino]-5,6-dihydroxy-anthraquinone
• 英文别名: 9,10-Anthracenedione, 5,8-bis((2-(dimethylamino)ethyl)amino)-1,2-dihydroxy-；5,8-bis[2-(dimethylamino)ethylamino]-1,2-dihydroxyanthracene-9,10-dione
• CAS: 69837-16-7
• 化学式: C₂₂H₂₈N₄O₄
• 分子量: 412.489
• InChiKey: FJSGMFGNISZAGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  醌茜素 在 四甲基乙二胺 、 溶剂黄146 、 锌 作用下， 生成 1,4-Bis[(2-dimethylaminoethyl)amino]-5,6-dihydroxy-anthraquinone
  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

• US4138415A
  申请人：——

  公开号：US4138415A

  公开（公告）日：1979-02-06
• 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.