1,4-Dihydroxy-5,8-bis[3-(2-hydroxyethylamino)propylamino]anthracene-9,10-dione | 73542-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-Dihydroxy-5,8-bis[3-(2-hydroxyethylamino)propylamino]anthracene-9,10-dione
• CAS: 73542-16-2
• 化学式: C₂₄H₃₂N₄O₆
• 分子量: 472.541
• InChiKey: VOSJYOUUOXAFHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  163
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-羟乙胺丙胺 、 2,3-二氢-1,4,5,8-四羟基-9,10-蒽醌 生成 1,4-Dihydroxy-5,8-bis[3-(2-hydroxyethylamino)propylamino]anthracene-9,10-dione
  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

• Polymeric(((oxazolidinyl)alkyl)amino)anthraquinones
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0122417A2

  公开（公告）日：1984-10-24

  This disclosure describes novel polymeric 1,4-bis-[(1,3-oxazolidin-3-yl) alkylamino] anthraquinones prepared by condensation of 1,4-bis-[(2-hydroxyalkyl-amino) alkylamino] anthraquinones with dialdehydes which are useful as anticancer agents.

  本公开介绍了新型聚合物 1,4-双-[(1,3-噁唑烷-3-基)烷基氨基]蒽醌，其制备方法是将 1,4-双-[(2-羟基烷基氨基)烷基氨基]蒽醌与可用作抗癌剂的二醛缩合。
• US4526788A
  申请人：——

  公开号：US4526788A

  公开（公告）日：1985-07-02
• US4614618A
  申请人：——

  公开号：US4614618A

  公开（公告）日：1986-09-30
• US4715993A
  申请人：——

  公开号：US4715993A

  公开（公告）日：1987-12-29
• 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.