Derivatives Incorporating Acridine, Pyrrole, and Thiazolidine Rings as Promising Antitumor Agents.

HR MS spectroscopy IR spectroscopy NMR spectroscopy X-ray analysis acridine antiproliferative activity pyrrole thiazolidine

Journal

Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009

Informations de publication

Date de publication:
14 Sep 2023
Historique:
received: 27 08 2023
revised: 10 09 2023
accepted: 12 09 2023
medline: 29 9 2023
pubmed: 28 9 2023
entrez: 28 9 2023
Statut: epublish

Résumé

Derivatives combining acridine, pyrrole, and thiazolidine rings have emerged as promising candidates in the field of antitumor drug discovery. This paper aims to highlight the importance of these three structural motifs in developing potent and selective anticancer agents. The integration of these rings within a single molecule offers the potential for synergistic effects, targeting multiple pathways involved in tumor growth and progression. Spiro derivatives were efficiently synthesized in a two-step process starting from isothiocyanates and 2-cyanoacetohydrazide. The thiourea side chain in spiro derivatives was utilized as a key component for the construction of the thiazolidine-4-one ring through regioselective reactions with bifunctional reagents, namely methyl-bromoacetate, dietyl-acetylenedicarboxylate, ethyl-2-bromopropionate, and ethyl-2-bromovalerate. These reactions resulted in the formation of a single regioisomeric product for each derivative. Advanced spectroscopic techniques, including 1D and 2D NMR, FT-IR, HRMS, and single-crystal analysis, were employed to meticulously characterize the chemical structures of the synthesized derivatives. Furthermore, the influence of these derivatives on the metabolic activity of various cancer cell lines was assessed, with IC

Identifiants

pubmed: 37764394
pii: molecules28186616
doi: 10.3390/molecules28186616
pmc: PMC10537105
pii:
doi:

Substances chimiques

Acridines 0
Pyrroles 0
Thiazolidines 0
Antineoplastic Agents 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

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Auteurs

Monika Garberová (M)

Institute of Chemistry, Faculty of Science, Pavol Jozef Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia.

Ivan Potočňák (I)

Institute of Chemistry, Faculty of Science, Pavol Jozef Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia.

Monika Tvrdoňová (M)

Institute of Chemistry, Faculty of Science, Pavol Jozef Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia.

Monika Majirská (M)

Department of Pharmacology, Faculty of Medicine, Pavol Jozef Šafárik University, Trieda SNP 1, 040 01 Košice, Slovakia.

Martina Bago-Pilátová (M)

Department of Pharmacology, Faculty of Medicine, Pavol Jozef Šafárik University, Trieda SNP 1, 040 01 Košice, Slovakia.

Slávka Bekešová (S)

Thermo Fisher Scientific, Mlynské Nivy 5, 821 09 Bratislava, Slovakia.

Andrej Kováč (A)

Department of Pharmacology and Toxicology, University of Veterinary Medicine and Pharmacy, Komenského 73, 041 81 Košice, Slovakia.
Institute of Neuroimmunology, Slovak Academy of Sciences, Dúbravská Cesta 9, 845 10 Bratislava, Slovakia.

Peter Takáč (P)

Department of Pharmacology and Toxicology, University of Veterinary Medicine and Pharmacy, Komenského 73, 041 81 Košice, Slovakia.

Krutika Khiratkar (K)

Institute of Neuroimmunology, Slovak Academy of Sciences, Dúbravská Cesta 9, 845 10 Bratislava, Slovakia.

Zuzana Kudličková (Z)

Institute of Chemistry, Faculty of Science, Pavol Jozef Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia.

Ján Elečko (J)

Institute of Chemistry, Faculty of Science, Pavol Jozef Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia.

Mária Vilková (M)

Institute of Chemistry, Faculty of Science, Pavol Jozef Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia.

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