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Triguanide Derivatives: Synthesis, Crystal Structure and Evaluation of the Proliferation Effect on Some Tumor Cell Lines


Štrukil, Vjekoslav; Glasovac, Zoran; Đilović, Ivica; Matković-Čalogović, Dubravka; Šuman, Lidija; Kralj, Marijeta; Eckert-Maksić, Mirjana
Triguanide Derivatives: Synthesis, Crystal Structure and Evaluation of the Proliferation Effect on Some Tumor Cell Lines // European journal of organic chemistry, 2012 (2012), 34; 6758-6797 doi:10.1002/ejoc.201200979 (međunarodna recenzija, članak, znanstveni)


Naslov
Triguanide Derivatives: Synthesis, Crystal Structure and Evaluation of the Proliferation Effect on Some Tumor Cell Lines

Autori
Štrukil, Vjekoslav ; Glasovac, Zoran ; Đilović, Ivica ; Matković-Čalogović, Dubravka ; Šuman, Lidija ; Kralj, Marijeta ; Eckert-Maksić, Mirjana

Izvornik
European journal of organic chemistry (1434-193X) 2012 (2012), 34; 6758-6797

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Medicinal chemistry ; antitumor agents ; antiproliferation ; nitrogen heterocycles ; rReaction mechanisms ; tautomerism

Sažetak
One-pot synthesis of new pentasubstituted triguanides 1a–e starting from the corresponding monosubstituted guanidine derivatives and diisopropylcarbodiimide is described and a mechanism for formation of the products observed is proposed. The structures of 1a–d were elucidated by spectroscopic analyses of their acetate salts. The structure of compound 1e was also confirmed by X-ray crystallography using its sulfate salt. The X-ray structure provided strong evidence of extensive electron delocalization within the triguanide core despite its non-planar structure. In addition, the effect of tautomerism on the course of the reaction, with emphasis on possible reaction paths leading to the side products, is discussed in some detail. Finally, antiproliferative effects of the acetate salts of the newly prepared compounds on five cancer lines in vitro were evaluated. It was found that acetates of 1a–c exhibit strong cytostatic and cytotoxic activity, with the strongest effect observed for the acetate of benzyl derivative 1c.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Marijeta Kralj, )
098-0982933-2920 - Organski i bioorganski procesi u osnovnom i elektronski pobuđenim stanjima (Mirjana Maksić, )
119-1193079-1084 - Strukturno istraživanje bioloških makromolekula metodom rentgenske difrakcije (Dubravka Matković-Čalogović, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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