Aromatic isothiocyanatopropenones and thiourea derivatives. Synthesis and biological properties
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BARBA, Nicanor, GULYA, Aurelian, POPUSHOI, Ana, LOZAN-TYRSHU, K., POIRIER, Donald. Aromatic isothiocyanatopropenones and thiourea derivatives. Synthesis and biological properties. In: Buletinul Academiei de Ştiinţe a Moldovei. Ştiinţele vieţii, 2014, nr. 1(322), pp. 146-160. ISSN 1857-064X.
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Buletinul Academiei de Ştiinţe a Moldovei. Ştiinţele vieţii
Numărul 1(322) / 2014 / ISSN 1857-064X

Aromatic isothiocyanatopropenones and thiourea derivatives. Synthesis and biological properties
CZU: 579.61:615.281.9

Pag. 146-160

Barba Nicanor1, Gulya Aurelian1, Popushoi Ana1, Lozan-Tyrshu K.2, Poirier Donald3
 
1 Moldova State University,
2 ”Nicolae Testemițanu” State University of Medicine and Pharmacy,
3 Universitatea Laval
 
Disponibil în IBN: 24 iulie 2014


Rezumat

În prezenta lucrare se descriu metode de sinteză a unor propenone aromatice cu grupe tioamidice sau izotiocian şi caracteristica lor biologică in vitro. Prin condensarea în cataliză acidă sau bazică a 4-(dimetilamino)benzaldehidei 4-Hidroxi-3-metoxibenzaldehidei şi furan-2-carbaldehidei cu 3-(4-acetilfenil)-1,1dimetiltioureea au fost obţinute propenone aromatice cu grupări –NHCSN(CH3)2, care la tratare termică sau în prezenţă de agenţi cu caracter acid (HCl, H2SO4, (CH3CO)2O, CH3COCl) elimină dimetilamină, transformîndu-se în izotiocianato -propenon cu randamentul de 54-92 %. La tratarea izotiocianatopropenonelor cu amine primare au fost obţinuti derivaţi cu grupări tioamidice-NHCSNH. Structura compuşilor noi obţinuţi cu conţinut de sulf a fost confirmată prin analiză elementală şi spectrală IR, 1H-, 13C- RMN. Compuşii sintetizaţi au fost testaţi ca inhibitori ai proliferării celulelor leucemice (HL-60), iar pentru produşii care au manifestat proprietăţi mai ponunţate, a fost testată in vitro activitatea lor antibacteriană faţă de unele microorganisme gram-pozitive şi gram-negative: Escherichia coli, Staphylococcus aureus, Shigella sonnei, Salmonella abony şi Bacillus cereus.

This paper is devoted to the methods of synthesis of aromatic propenones containing thioamidic or isothiocyan groups and their in vitro biological characteristics. Aromatic propenones with the NHCSN(CH3)2-group have been obtained by catalytic condensation of 4-(dimethylamino)benzaldehyde, 4-hydroxy-3-methoxybenzaldehyde and furan-2-carbaldehyde with 3-(4-acetylphenyl)-1,1-dimethylthiourea in acid or base medium. These aromatic propenones removed dimethylamine and transformed into isothiocyanatopropenones with 54-92% yields by means of thermal treatment or in the presence of acid agents (HCl, H2SO4,(CH3CO)2O, CH3COCl). Derivatives with NHCSNH thioamidic group have been obtained by treating isothiocyanatopropenones with primary amines. The structures of the new sulphur containing compounds have been confirmed by means of elemental analysis and IR, 1H NMR, 13C NMR and mass spectra. All the compounds were tested as inhibitors of HL-60 leukemia cell proliferation and the most potent of them have been also tested for their in vitro antibacterial activity against some gram-positive and gram-negative microorganisms: Escherichia coli, Staphylococcus aureus, Shigella sonnei, Salmonella abony, and Bacillus cereus.

Были получены новые координационные соединения меди (II) содержащие 4- фенилтиoсемикарбазон 2-формилпиридина и сульфаниламиды с выраженной антибактериальной активностью по отношению к бактериям рода Bacillus сеreus, а также к другим грамположительным и грамотрицательным микроорганизмам. Выявленные антимикробные свойства позволяют рекомендовать соответствующие комплексы меди (II) с 4- фенилтисемикарбазоном 2-формилпиридина и сульфаниламидами для применения в медицинской практике против резистентных штаммов микроорганизмов.

Cuvinte-cheie
chalconă, izotiocianatopropenonă, propenonă, inhibitori ai proliferării

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