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Estimated results:
- development of competitive new antimicrobial, fungicidic substances and growth regulators of plants on the basis of phenothiazinic, sulfurcontaining naphthoquinonic and thiosulfonatic derivatives;
- development of preparative methods of synthesis of most new perspective, earlier not studied sulfurcontaining hetero- and carbocyclic compounds and evaluations of their physical and chemical properties;
- establishment of dependence "structure-action" on the basis of experimental data of biological research and methods of computer-calculations with bringing in the internet on-line software;
- establishment of minimum acting concentrations and selection of low toxic of the synthesized compounds - perspective substances for creation of antimicrobial, fungicidic and growth regulative preparations;
- expansion of order of valuable sulfurcontaining synthones for the obtain of potential physiological active compounds.
Collaboration results:
The collective articles will be published in professional native and foreign publishers as a result of implementation of Project
After every visit to the partner University will be elaborate scientifical reports.
The results of project are also got will be used in an educational process, calculated, laboratorial, master's degree and dissertation works.
Final Results
Within the bilateral cooperation between Romania and Ukraine 5 new 10-sulfonyl-benzo-phenothiazine compounds were obtained by classical reactions and under microwave irradiation. These substances were characterized by IR, NMR (1H NMR, 13C NMR), elemental analysis and by mass spectrometry. 4 New pyrazol-benzene-sulfonamide compounds were obtained and characterized by mass spectrometry. The 10-acetyl -, and 10-formyl-phenotiazine compounds were obtained as precursors for regioselective fuctionalization with chlorosulfonic acid. From this reaction 10-acetyl-10H-phenothiazine-2-sulfonic acid and respectively 10-formyl-10H-phenothiazine-2-sulfonic acid were obtained, but because of their low stability these two substances were further transformed into 10-acetyl-10H-phenothiazine-2-chlorosulfonic acid and 10-formyl-10H-phenothiazine-2-chlorosulfonic acid respectively. These substances were characterized by mass spectrometry. New sulfonamide derivative obtained starting with 10-formyl-10H-phenothiazine-2-chlorosulfonic acid and N1, N1-dimetilpropan-1, 3-diamine was characterized by IR and mass spectrometry.
New heterocyclic Schiff bases were obtained in good yields by thermal condensation of 10-alkyl-3-formyl-10H-phenothiazine derivatives with aromatic amines as precursors for fuctionalization with chlorosulfonic acid. Structural characterization was based on high resolution NMR, UV-Vis and fluorescence spectroscopy.
Prediсtive computer screening of biological activity of new sulfur-containing derivatives of 1,4-naphthoquinone and thiosulfoacides, their salts and S-esthers of thiosulfoacides with nitrogencontaining heterocyclic, carbocyclic, aliphatic, functionally substituted aliphatic and different substituent was carried out with the use of the program PASS S&T and priority directions of the experimental research were shown, in particular: investigation of antitumor, antidiabetic, anti-virus, anaesthetic, antiasthmatic, antiprotozoal, antifungal, anthelmintic, antialcohol effects.
Interaction of sodium and potassium salts of aliphatic thiosulfoacids with 2,4,6-trichlorо-1,3,5-trizine was investigated. 2,4-dichlor-1,3,5-triazine S-esthers of aliphatic thiosulfoacides were obtained. Ability of 6-chlor-2,4-bis(alkylsulfonylthio)-sym-triazines to hydrolysis with obtaining of 2,4-bis(alkylsulfonylthio)-1,3,5-triazines-6 was found. The preparative methods of acylation of alkyl S-esthers of 4-aminobenzenethiosulfoacid by cyanurchloride were developed and terms of passing of these reactions were investigated.
New substituted 1,4-naphthoquinone – thiols, sulfides and sulfenamides were synthesized.
New phenothiazine derivatives containing disulfide, thiol and sulfide functional groups were synthesized. The reaction of cyclization with formation of new thiazoline derivatives of phenothiazine were carried out on the basis of synthesized thiosemicarbazone derivative of 2-chloro-phenothiazine. These substances were characterized by NMR, IR and elemental analysis.
On the basis of interaction of 2-amino-3-carbetoxynaphtho[2,3-b]thiphene-4,9-diones with various arylchloranhydrides in different terms were synthesized 2-arylamino-3-carbethoxynaphtho[2,3-b]thiophene-4,9-diones, which at a reaction with dichlortriphenylphosphorane resulted the formation of 2-aryl-4Н-naphtho[2’,3’:4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones.
The structure of the obtained compounds were confirmed by results of NMR, IR, mass-spectroscopies, element analysis.
For the new 10-sulfonyl-benzo-phenothiazine compounds and for some substituted naphthalene-1,4-dione derivatives the biological activity was assigned using the PASS biological activity prediction program.
As a result of this joint research activities carried under the frame of this bilateral project in 2009 one scientific article was accepted for publication in the journal (covered by Thomson Routers products) Studia UBB “Chemia” Emese Gál, Luiza Găină, Tamás Lovász, Castelia Cristea and Luminiţa Silaghi-Dumitrescu «Synthesis and fluorescence properties of new Schiff bases containing phenothiazine units», and one manuscript was acceptted in "Organic Chemistry International": М.V. Stasevych, R.Ya. Musyanovych, S.V. Vasylyuk, V.I. Lubenets, V.P. Novikov, E. Gál, L. Silaghi-Dumitrescu «Synthesis of new sulfur- and nitrogencontaining phenothiazine derivatives».
As a result of implementation of project 2 articles were published in 2008:
- S. V. Vasylyuk, V. I. Lubenets, Yu. I. Bychko, and V. P. Novikov «Interaction of cyanuric chloride with alkanethiosulfonates» / Chemistry of Heterocyclic Compounds. – 2008. - Vol. 44. - №. 1. – Р. 111-112.
- M.V. Stasevych, S.I.Sabat, M.I. Semenyuk, R.Ya.Musyanovych, V.P. Novikov «2-Аryl-4Н-naphtho[2’,3’:4,5]thieno[2,3-d][1,3]oxazine-4,5,10-triones» Chemistry of Heterocyclic Compounds. – 2008. – Vol. 44. - № 7. – Р.897-898.
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