1,4-bis[3-(dimethylamino)propionamido]-9,10-anthracenedione | 115290-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-bis[3-(dimethylamino)propionamido]-9,10-anthracenedione
• 英文别名: 3-(dimethylamino)-N-[4-[3-(dimethylamino)propanoylamino]-9,10-dioxoanthracen-1-yl]propanamide
• CAS: 115290-33-0
• 化学式: C₂₄H₂₈N₄O₄
• 分子量: 436.511
• InChiKey: MOLNOJMQDXFBME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二甲胺 、 N,N'-(9,10-dioxo-9,10-dihydroanthracene-1,4-diyl)bis(3-chloropropanamide) 以 乙醇 为溶剂， 反应 0.5h， 以91%的产率得到1,4-bis[3-(dimethylamino)propionamido]-9,10-anthracenedione
  参考文献：
  名称：

  1,4- and 2,6-Disubstituted Amidoanthracene-9,10-dione Derivatives as Inhibitors of Human Telomerase

  摘要：

  A number of 1,4- and 2,6-difunctionalized amidoanthracene-9, l0-diones have been prepared. We have examined their in vitro cytotoxicity in several tumor cell lines and their ability to inhibit the telomere-addition function of the human telomerase enzyme together with their inhibition of the Taq polymerase enzyme. Compounds with -(CH2)(2)- side chains terminating in basic groups such as piperidine show inhibition of telomerase at (IC50)-I-tel levels of 4-11 mu M. These are thus among the most potent nonnucleoside telomerase inhibitors reported to date. Cytotoxicity levels in human tumor cell lines were at comparable levels for several compounds. Implications for amidoanthracene-9,10-dione telomerase inhibitors as potential anticancer agents are discussed.

  DOI：

  10.1021/jm9801105

文献信息

• [EN] ANTHRAQUINONES WITH BIOLOGICAL ACTIVITY<br/>[FR] ANTHRAQUINONES A ACTIVITE BIOLOGIQUE
  申请人：CANCER RESEARCH CAMPAIGN TECHNOLOGY LIMITED

  公开号：WO1998025885A1

  公开（公告）日：1998-06-18

  (EN) Novel 1,4- and 2,6-substituted anthracene-9,10-diones ('9,10-anthraquinones'). The use of the novel compounds and known 1,4- and 2,6-substituted anthracene-9,10-diones ('9,10-anthraquinones') in the inhibition of telomerase activity and/or their use in the treatment of cancer.(FR) La présente invention concerne de nouveaux anthracène-9,10-diones 1,4- et 2,6-substitués ('9,10-anthraquinones'), ainsi que l'utilisation de ces nouveaux composés et des anthracène-9,10-diones 1,4- et 2,6-substitués ('9,10-anthraquinones') connus dans l'inhibition de l'activité de la télomérase et/ou leur utilisation dans le traitement du cancer.
• 1,4- and 2,6-Disubstituted Amidoanthracene-9,10-dione Derivatives as Inhibitors of Human Telomerase
  作者：Philip J. Perry、Sharon M. Gowan、Anthony P. Reszka、Paolo Polucci、Terence C. Jenkins、Lloyd R. Kelland、Stephen Neidle

  DOI：10.1021/jm9801105

  日期：1998.8.1

  A number of 1,4- and 2,6-difunctionalized amidoanthracene-9, l0-diones have been prepared. We have examined their in vitro cytotoxicity in several tumor cell lines and their ability to inhibit the telomere-addition function of the human telomerase enzyme together with their inhibition of the Taq polymerase enzyme. Compounds with -(CH2)(2)- side chains terminating in basic groups such as piperidine show inhibition of telomerase at (IC50)-I-tel levels of 4-11 mu M. These are thus among the most potent nonnucleoside telomerase inhibitors reported to date. Cytotoxicity levels in human tumor cell lines were at comparable levels for several compounds. Implications for amidoanthracene-9,10-dione telomerase inhibitors as potential anticancer agents are discussed.