Synthesis of Norabietyl and Nordehydroabietyl Imidazolidine-2,4,5-Triones and Their Activity against Tyrosyl-DNA Phosphodiesterase 1

被引：2
|
作者：
Kovaleva, Kseniya S. [1 ]
Yarovaya, Olga I. [1 ]
Chernyshova, Irina A. [2 ]
Zakharenko, Alexandra L. [2 ]
Cheresiz, Sergey V. [3 ]
Azimirad, Amirhossein [3 ]
Pokrovsky, Andrey G. [3 ]
Lavrik, Olga I. [2 ]
Salakhutdinov, Nariman F. [1 ]
机构：
[1] Russian Acad Sci, N N Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentiev Ave 9, Novosibirsk 630090, Russia
[2] Russian Acad Sci, Novosibirsk Inst Chem Biol & Fundamental Med, Siberian Branch, Lavrentiev Ave 8, Novosibirsk 630090, Russia
[3] Novosibirsk State Univ, V Zelman Inst Med & Psychol, Pirogova St 1, Novosibirsk 630090, Russia
来源：
MOLBANK | 2023年 / 2023卷 / 04期
基金：
俄罗斯科学基金会;
关键词：
resin acids; TDP1; inhibitors; heterocyclic compounds; DNA repair; parabanic acid; adamantane; dehydroabietic acid; abietic acid; TDP1; INHIBITORS;
D O I：
10.3390/M1743
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New imidazolidine-2,4,5-triones with norabietic, nordehydroabietic, and adamantane substituents were synthesized by reacting oxalyl chloride and the corresponding ureas, providing good yields. Bioisosteric replacement of the ureide group with a parabanic acid fragment made it possible to increase the solubility of compounds and conduct biological studies. The compounds inhibit the DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 in submicromolar concentrations. Cytotoxic concentrations were also studied on the glioblastoma cell line SNB19.
引用
收藏
页数：8
相关论文
共 50 条
  • [31] Poly(ADP-ribose) polymerase 1 stimulates the AP-site cleavage activity of tyrosyl-DNA phosphodiesterase 1
    Lebedeva, Natalia A.
    Anarbaev, Rashid O.
    Sukhanova, Maria
    Vasil'eva, Inna A.
    Rechkunova, Nadejda I.
    Lavrik, Olga I.
    BIOSCIENCE REPORTS, 2015, 35
  • [32] Combining a Nanosensor and ELISA for Measurement of Tyrosyl-DNA Phosphodiesterase 1 (TDP1) Activity and Protein Amount in Cell and Tissue Extract
    Jakobsen, Ann-Katrine
    Stougaard, Magnus
    NANO LIFE, 2015, 5 (02)
  • [33] The influence of an enamine usnic acid derivative (a tyrosyl-DNA phosphodiesterase 1 inhibitor) on the therapeutic effect of topotecan against transplanted tumors in vivo
    Nikolin, V. P.
    Popova, N. A.
    Kaledin, V., I
    Luzina, O. A.
    Zakharenko, A. L.
    Salakhutdinov, N. F.
    Lavrik, O., I
    CLINICAL & EXPERIMENTAL METASTASIS, 2021, 38 (05) : 431 - 440
  • [34] Synthesis and Biological Activities of 11-and 12-Substituted Benzophenanthridinone Derivatives as DNA Topoisomerase IB and Tyrosyl-DNA Phosphodiesterase 1 Inhibitors
    Yang, Hao
    Qin, Chao
    Wu, Min
    Wang, Fang-Ting
    Wang, Wenjie
    Agama, Keli
    Pommier, Yves
    Hu, De-Xuan
    An, Lin-Kun
    CHEMMEDCHEM, 2023,
  • [35] New Dual Inhibitors of Tyrosyl-DNA Phosphodiesterase 1 and 2 Based on Deoxycholic Acid: Design, Synthesis, Cytotoxicity, and Molecular Modeling
    Salomatina, Oksana V.
    Kornienko, Tatyana E.
    Zakharenko, Alexandra L.
    Komarova, Nina I.
    Achara, Chigozie
    Reynisson, Johannes
    Salakhutdinov, Nariman F.
    Lavrik, Olga I.
    Volcho, Konstantin P.
    MOLECULES, 2024, 29 (03):
  • [36] A Novel Class of Tyrosyl-DNA Phosphodiesterase 1 Inhibitors That Contains the Octahydro-2H-chromen-4-ol Scaffold
    Li-Zhulanov, Nikolai S.
    Zakharenko, Alexandra L.
    Chepanova, Arina A.
    Patel, Jinal
    Zafar, Ayesha
    Volcho, Konstantin P.
    Salakhutdinov, Nariman F.
    Reynisson, Johannes
    Leung, Ivanhoe K. H.
    Lavrik, Olga I.
    MOLECULES, 2018, 23 (10):
  • [37] The influence of an enamine usnic acid derivative (a tyrosyl-DNA phosphodiesterase 1 inhibitor) on the therapeutic effect of topotecan against transplanted tumors in vivo
    V. P. Nikolin
    N. A. Popova
    V. I. Kaledin
    O. A. Luzina
    A. L. Zakharenko
    N. F. Salakhutdinov
    O. I. Lavrik
    Clinical & Experimental Metastasis, 2021, 38 : 431 - 440
  • [38] Synthesis and Biological Evaluation of Indenoisoquinolines That Inhibit Both Tyrosyl-DNA Phosphodiesterase I (Tdp1) and Topoisomerase I (Top1)
    Conda-Sheridan, Martin
    Reddy, P. V. Narasimha
    Morrell, Andrew
    Cobb, Brooklyn T.
    Marchand, Christophe
    Agama, Keli
    Chergui, Adel
    Renaud, Amelie
    Stephen, Andrew G.
    Bindu, Lakshman K.
    Pommier, Yves
    Cushman, Mark
    JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (01) : 182 - 200
  • [39] Synthesis and Biological Evaluation of the First Dual Tyrosyl-DNA Phosphodiesterase I (Tdp1)-Topoisomerase I (Top1) Inhibitors
    Trung Xuan Nguyen
    Morrell, Andrew
    Conda-Sheridan, Martin
    Marchand, Christophe
    Agama, Keli
    Bermingam, Alun
    Stephen, Andrew G.
    Chergui, Adel
    Naumova, Alena
    Fisher, Robert
    O'Keefe, Barry R.
    Pommier, Yves
    Cushman, Mark
    JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (09) : 4457 - 4478
  • [40] Dehydroabietylamine-based thiazolidin-4-ones and 2-thioxoimidazolidin-4-ones as novel tyrosyl-DNA phosphodiesterase 1 inhibitors
    Kseniya Kovaleva
    Evgeniya Mamontova
    Olga Yarovaya
    Olga Zakharova
    Alexandra Zakharenko
    Olga Lavrik
    Nariman Salakhutdinov
    Molecular Diversity, 2021, 25 : 2389 - 2397
12345