2,6-bis(3-piperidinopropionamido)anthraquinone | 134888-32-7

• 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-piperidinopropionamido)anthraquinone
• 英文别名: N,N'-(9,10-Dihydro-9,10-dioxo-2,6-anthracenediyl)bis-1-piperidinepropanamide；N-[9,10-dioxo-6-(3-piperidin-1-ylpropanoylamino)anthracen-2-yl]-3-piperidin-1-ylpropanamide
• CAS: 134888-32-7
• 化学式: C₃₀H₃₆N₄O₄
• 分子量: 516.64
• InChiKey: GUSIRLMAICXUKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  2,6-二氨基蒽醌 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醇 为溶剂， 反应 10.0h， 生成 2,6-bis(3-piperidinopropionamido)anthraquinone
  参考文献：
  名称：

  Anthracene-9,10-diones as potential anticancer agents. Synthesis, DNA-binding, and biological studies on a series of 2,6-disubstituted derivatives

  摘要：

  A series of 2,6-bis(omega-aminoalkanamido)anthracene-9,10-diones (9,10-anthraquinones), of general formula Ar(NHCO(CH2)nNR2)2, where Ar = anthracene-9,10-dione and n = 1 or 2, have been synthesized by treatment of the corresponding bis(omega-haloalkanamido) derivatives with appropriate secondary amines. The DNA-binding properties of these compounds were evaluated by thermal denaturation studies, unwinding of closed-circular DNA, determination of association constants in solution, and examined by molecular modeling. A representative compound in the series has been examined by X-ray crystallography. In vitro cytotoxicity data is reported for the compounds and some indications of structure-activity relationships have been discerned. In particular, those compounds with two methylene links (n = 2) in each side chain separating the amide and terminal amine moieties have superior activity and, in general, enhanced DNA binding characteristics. It is postulated that the mode of reversible binding of these compounds to DNA involves the side chains occupying both major and minor grooves and, further, that this may confer cytotoxic properties which are distinct from those of previously reported anthracene-9,10-dione cytotoxins.

  DOI：

  10.1021/jm00086a010

文献信息

• Molecular rec§ognition of telomere DNA sequence by 2, 6 anthraquinone derivatives leads to thermal stabilization and induces apoptosis in cancer cells
  作者：Arpita Dey、Kumud Pandav、Mala Nath、Ritu Barthwal、Ramasare Prasad

  DOI：10.1016/j.ijbiomac.2022.08.156

  日期：2022.11

  significant fluorescence quenching and changes in ellipticity resulting in external binding of both the ligands to G-quadruplex DNA. Ligand binding induced enhancement of thermostability of G4 DNA is greater in Na environment (Δ = 34 °C) as compared to that in K environment (Δ = 21 °C), thereby restricting telomerase binding access to telomeres. Microscopic images of treated cells indicated cellular shape

  根据目前的研究，抗癌蒽醌会影响端粒破坏，并可能与触发细胞凋亡信号的 G-四链体 DNA 相互作用。本研究代表了与实验室合成的基于哌啶的蒽醌衍生物 2, 6- 双 [(3-哌啶基)乙酰氨基)] 蒽-9,10- 结合后，癌细胞中氧化应激、晚期细胞凋亡和诱导衰老的生物物理学研究二酮 (N1P) 和 2, 6-双[哌啶基)丙酰胺基]蒽-9,10-二酮 (N2P)，具有 G-四链体 DNA。我们采用生物物理方法来探索合成蒽醌衍生物与四链体 DNA 序列的相互作用，以影响 K 和 Na 阳离子存在下的生物活性。 N2P 和 N1P 的结合亲和力分别为 = 5.8 × 10 M 和 = 1.0 × 10 M，导致低/高色度，红移 5–7 nm，显着的荧光猝灭和椭圆度变化，导致外部结合两者都是 G-四链体 DNA 的配体。与 K 环境 (Δ = 21 °C) 相比，Na 环境 (Δ = 34 °C) 中配体结合诱导的
• Compositions to improve the therapeutic benefit of bisantrene and analogs and derivatives thereof
  申请人：Race Oncology Ltd.

  公开号：US10548876B2

  公开（公告）日：2020-02-04

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to bisantrene or derivatives, analogs, or prodrugs thereof.

  本发明描述了通过提高单一疗法的疗效或减少副作用来改善以前因治疗效果不理想而受到限制的治疗剂的疗效的方法和组合物。这些方法和组合物尤其适用于双蒽或其衍生物、类似物或原药。
• Combinatorial methods to improve the therapeutic benefit of bisantrene and analogs and derivatives thereof
  申请人：Race Oncology Ltd.

  公开号：US11147800B2

  公开（公告）日：2021-10-19

  The present invention describes methods and compositions for improving the therapeutic efficacy of therapeutic agents previously limited by suboptimal therapeutic performance by either improving efficacy as monotherapy or reducing side effects. Such methods and compositions are particularly applicable to bisantrene or derivatives, analogs, or prodrugs thereof.

  本发明描述了通过提高单一疗法的疗效或减少副作用来改善以前因治疗效果不理想而受到限制的治疗剂的疗效的方法和组合物。这些方法和组合物尤其适用于双蒽或其衍生物、类似物或原药。
• Reduction of hair growth
  申请人：——

  公开号：US20030012755A1

  公开（公告）日：2003-01-16

  Mammalian hair growth is reduced by applying an inhibitor of telomerase to the skin.

  在皮肤上涂抹端粒酶抑制剂可减少哺乳动物毛发的生长。
• INTERCALATING AGENTS
  申请人：CANCER RESEARCH CAMPAIGN TECHNOLOGY LTD.

  公开号：EP0482119A1

  公开（公告）日：1992-04-29