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
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 17 条
  • [1] 1,3-Substituted Imidazolidine-2,4,5-triones: Synthesis and Inhibition of Cholinergic Enzymes
    Pejchal, Vladimir
    Stepankova, Sarka
    Padelkova, Zdenka
    Imramovsky, Ales
    Jampilek, Josef
    MOLECULES, 2011, 16 (09): : 7565 - 7582
  • [2] Synthesis and inhibitory activity of 1,3-(adamantan-1(2)-yl)- imidazolidine-2,4,5-triones and 3,3'-(adamantan-1-yl)- bis(1-alkylimidazolidine-2,4,5-triones)
    D'yachenko, Vladimir S.
    Burmistrov, Vladimir V.
    Nishi, Kosuke
    Kim, In-Hae
    Butov, Gennady M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (10) : 1080 - 1083
  • [3] Synthesis and inhibitory activity of 1,3-(adamantan-1(2)-yl)- imidazolidine-2,4,5-triones and 3,3'-(adamantan-1-yl)- bis(1-alkylimidazolidine-2,4,5-triones)
    Vladimir S. D’yachenko
    Vladimir V. Burmistrov
    Kosuke Nishi
    In-Hae Kim
    Gennady M. Butov
    Chemistry of Heterocyclic Compounds, 2017, 53 : 1080 - 1083
  • [4] Dual DNA topoisomerase 1 and tyrosyl-DNA phosphodiesterase 1 inhibition for improved anticancer activity
    Zakharenko, Alexandra
    Dyrkheeva, Nadezhda
    Lavrik, Olga
    MEDICINAL RESEARCH REVIEWS, 2019, 39 (04) : 1427 - 1441
  • [5] AP-site cleavage activity of tyrosyl-DNA phosphodiesterase 1
    Lebedeva, Natalia A.
    Rechkunova, Nadejda I.
    Lavrik, Olga I.
    FEBS LETTERS, 2011, 585 (04): : 683 - 686
  • [6] Human Tyrosyl-DNA Phosphodiesterase 1 Possesses Transphosphooligonucleotidation Activity With Primary Alcohols
    Dyrkheeva, Nadezhda
    Anarbaev, Rashid
    Lebedeva, Natalia
    Kuprushkin, Maxim
    Kuznetsova, Alexandra
    Kuznetsov, Nikita
    Rechkunova, Nadejda
    Lavrik, Olga
    FRONTIERS IN CELL AND DEVELOPMENTAL BIOLOGY, 2020, 8
  • [7] A fluorescence-based assay for the apurinic/apyrimidinic-site cleavage activity of human tyrosyl-DNA phosphodiesterase 1
    Thomson, Graeme J.
    Hamilton, Nicola S.
    Hopkins, Gemma V.
    Waddell, Ian D.
    Watson, Amanda J.
    Ogilvie, Donald J.
    ANALYTICAL BIOCHEMISTRY, 2013, 440 (01) : 1 - 5
  • [8] Synthesis of 11-aminoalkoxy substituted benzophenanthridine derivatives as tyrosyl-DNA phosphodiesterase 1 inhibitors and their anticancer activity
    Yang, Hao
    Wang, Fang-Ting
    Wu, Min
    Wang, Wenjie
    Agama, Keli
    Pommier, Yves
    An, Lin -Kun
    BIOORGANIC CHEMISTRY, 2022, 123
  • [9] 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,
  • [10] Design, synthesis, and evaluation of dehydroabietyl imidazolidine-2,4-diones, 2,4,5-triones, and 2-thioxoimidazolidine-4,5-diones as TDP1 inhibitors and dual TDP1/TDP2 inhibitors
    Kovaleva, Kseniya S.
    Yarovaya, Olga I.
    Gatilov, Yuriy V.
    Lastovka, Anastasiya V.
    Chernyshova, Irina A.
    Dyrkheeva, Nadezhda S.
    Chepanova, Arina A.
    Lavrik, Olga I.
    Salakhutdinov, Nariman F.
    ARCHIV DER PHARMAZIE, 2025, 358 (01)