Browsing by Author "Barba, Nicanor"

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    AROMATIC ISOTHIOCYANATOPROPENONES AND THIOUREA DERIVATIVES. SYNTHESIS AND BIOLOGICAL PROPERTIES
    (2014) Barba, Nicanor; Gulea, Aurelian; Popușoi, Ana; Lozan-Tîrșu, Carolina; Poirier, Donald
    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.
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    COMPOUNDS REMOVED FROM THE CONDENSATION REACTION BETWEEN 2 - ACETYLPYRIDINE AND 2 - FORMYLPYRIDINE. SYNTHESIS, CRYSTAL STRUCTURE AND BIOLOGICAL EVALUATION
    (Institutul de Chimie al AŞM, 2020) Rusnac, Roman; Botnaru, Maria; Barba, Nicanor; Petrenko, Peter; Chumakov, Yurii; Gulea, Aurelian
    The research is devoted to the study of unexpected products that formed as a result of the condensation reaction between 2-acetylpyridine and 2-formylpyridine under the Claisen-Schmidt reaction conditions. The structure of the compoundswas determined and confirmed using FTIR, 1H and 13 C NMR spectroscopy, and X-ray diffraction technique. As a result, a sequence of reactions leading to the following compounds has been proposed: 1,3-bis(pyridin -2-yl)prop-2-en-1-one (3); 1,3,5-tri(pyridin-2-yl)pentane-1,5-dione (4); (2,4-dihydroxy -2,4,6-tri(pyridin-2-yl)cyclohexyl)(pyridin-2-yl)methanone (5) and (4-hydroxy-2,4,6 -tri(pyridin-2-yl)cyclohexane-1,3-diyl)bis(pyridin-2-ylmethanone) (6) as well as2- formylpyridine (1) and 2-acetylpyridine (2). The plausible mechanisms of these chemical transformations and synthetic methods for obtaining substituted cyclohexanol derivatives are also presented. The synthesized compounds were tested for antimicrobial and antioxidant activity. The obtained results show that the compounds 4-6have moderate antifungal activity. The activity of compound 6is nine times higher towards Cryptococcus neoformans than the activity of Nistatinthat is used in medical practice. The present experimental results show that compound 6has potential application in antibacterial and antifungal areas.
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    SUBSTITUTED 1,3-PHENYL(PYRIDYL) PROPENONES AND DERIVATIVES WITH THIOSEMICARBAZIDIC GROUPS. STRUCTRURE – (HL-60) ANTILEUKEMIA ACTIVITY RELATIONSHI
    (Institute of Chemistry of ASM, 2014) Popuşoi, Ana; Barba, Nicanor; Gulea, Aurelian; Roy, Jenny; Poirier, Donald
    3-(4-(Dimethylamino)phenyl-1-(4-isothiocyanatophenyl)prop-2-en-1-one was obtained from the corresponding N,N-dimethylthyoureas by elimination of dimethylamine at heating with gaseous hydrogen chloride in chloroform and 1-(4-isothiocyanatophenyl)-3-(pyridin-2-il)prop-2-en-1-one by treating 1,1-dimethyl-3-(4-(3-(pyridin-2-il)-acryloyl)-phenyl)thyourea with acetic anhydride. The difference in the reactivity of the groups >C=O and NCS in the synthesis with hydrazine hydrate and its derivatives allows the synthesis of some 1,3-disubstituted propenones with thiosemicarbazide groups (4- and 1,4-disubstituted) in good yields. From 4-substituted thiosemicarbazides and 2-formilpyridine thiosemicarbazones were obtained. In the case of some derivatives, the propenone group in the reaction with hydrazine hydrate allows the formation of pyrazole derivatives. All obtained compounds were investigated for antileukemia activity. It was found that this activity is more pronounced for thiosemicarbazide derivatives with two pyridine nuclei at concentrations 10-5-10-7 mol/L.
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    SUBSTITUTED 1,3-PHENYL(PYRIDYL) PROPENONES AND DERIVATIVES WITH THIOSEMICARBAZIDIC GROUPS. STRUCTRURE – (HL-60) ANTILEUKEMIA ACTIVITY RELATIONSHIP
    (2014) Popușoi, Ana; Barba, Nicanor; Gulea, Aurelian; Roy, Jenny; Poirier, Donald
    3-(4-(Dimethylamino)phenyl-1-(4-isothiocyanatophenyl)prop-2-en-1-one was obtained from the corresponding N,N-dimethylthyoureas by elimination of dimethylamine at heating with gaseous hydrogen chloride in chloroform and 1-(4-isothiocyanatophenyl)-3-(pyridin-2-il)prop-2-en-1-one by treating 1,1-dimethyl-3-(4-(3-(pyridin-2-il)-acryloyl)-phenyl)thyourea with acetic anhydride. For all obtained compounds in the course of reaction the antileukemia activity was investigated.
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    SYNTHESIS AND ANTITUMOR PROPERTIES OF DERIVATIVES 4-SUBSTITUTED-5-(PIRIDIN-4-YL)-4H-1,2,4-TRIAZOLE-3-THIOL
    (Academia de Ştiinţe a Moldovei, 2015) Rusnac, Roman; Zatic, Ana; Paholnitscaia, Anastasia; Barba, Nicanor; Perreault, M.; Gulea, Aurelian
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    SYNTHESIS AND BIOLOGIC PROPERTIES OF SOME1-(ALCHYL) PHENYL-3-(4-(3-(PYRIDIN-2-IL)ACRYLOYL)PHENYLTHIOUREA
    (2013) Popușoi, Ana; Barba, Nicanor; Gulea, Aurelian; Roy, Jenny; Poirier, Donald; Prisacari, Viorel
    This paper describe the synthesis of some 1-(alchyl)aril-3-(4-(3-pyridin-2-il) acryloyl)phenylthiourea obtained by condensation of 2-pyridincarboxaldehide with some derivatives of 4-acetylphenilthioureas in basic medium or by addition of aliphatic and aromatic amines to the correspondingisothiocyanatopropenones. 12 new compounds were obtained and their biological properties were analysed. The substituted thioureas by pyridine radicals, morpholine and phenol show a maximum bacteriostatic activity for Gram positive microorganisms like: Staphylococcus Aureus and Enterococcus Faecalis at the minimum inhibitory concentration 9.37-37.5 μM. Antifungal activity for Candida Albicans, Aspergillus Niger, AspergillusFumigatus, Penicillium is weak, in minimum inhibitory concentration 600->600 μM. The leukemia activity like inhibitor (HL-60), is 84-96.9% at the concentration 10-5mol/l and 15-20% and at the concentrations 10-6, 10-7mol/l.