2,6-bis[3-(heptamethyleneimino)propionamido]anthracene-9,10-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-bis[3-(heptamethyleneimino)propionamido]anthracene-9,10-dione
• 英文别名: 3-(azocan-1-yl)-N-[6-[3-(azocan-1-yl)propanoylamino]-9,10-dioxoanthracen-2-yl]propanamide
• 化学式: C₃₄H₄₄N₄O₄
• 分子量: 572.748
• InChiKey: DOMCCQXROQQPDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  四氢吡咯 、 七亚甲基亚胺 、 2,6-bis(3-chloropropionamido)anthracene-9,10-dione 在 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到2,6-bis[3-(heptamethyleneimino)propionamido]anthracene-9,10-dione
  参考文献：
  名称：

  Molecular Modeling Studies on G-Quadruplex Complexes of Telomerase Inhibitors:  Structure−Activity Relationships

  摘要：

  Inhibition of the ability of the enzyme telomerase to add telomeric repeats to the end of chromosomes is a novel target for potential anticancer therapy. This paper examines the hypothesis that compounds possessing a planar aromatic chromophore inhibit telomerase via stabilization of, and binding to, a folded guanine quadruplex structure. Two series of telomerase inhibitors have been designed based on the 2,6-disubstituted amidoanthracene-9,10-dione and a,6-disubstituted acridine chromophores in order to investigate structure-activity relationships between biological activity and substituent group size. The relative binding energies between these compounds and the folded human telomere DNA quadruplex were determined using molecular simulation methods, involving explicitly solvated structures. The results obtained are in excellent agreement with the biological activity as measured in vitro using a modified TRAP assay and in general agreement with the ranking order of binding enthalpies found in isothermal titration calorimetry studies. This broad agreement provides strong support for the hypothesis that guanine quadruplexes are the primary target for telomerase inhibitors with extended planar chromophores.

  DOI：

  10.1021/jm990287e

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.