Chemical properties of 3-(5-amino-1H-1,2,4-triazol-1-yl)- and 3-(2-amino-1H-benzo[d]imidazol-1-yl)-3-phenylpropanehydrazides
DOI:
https://doi.org/10.24959/ophcj.14.806Keywords:
dihydro-7-phenyl-1, 2, 4-triazolo[1, 5-a]pyrimіdin-5-one, dihydro-4-phenylpyrimіdo[1, 2-a]benzіmіdazol- 2-one, hydrazinolysis, 3-(5-amіno-1, 4-triazolyl)-3-phenylpropanehydrazide, 3-(2-amіnobenzo[d]іmіdazolyl)- 3-phenylpropanehydrazide, chemical properties,Abstract
Reactions of 3-(5-amino-1H-1,2,4-triazol-1-yl)- and 3-(2-amіno-1H-benzo[d]іmіdazol-1-yl)-3-phenylpropanehydrazides with carbonyl electrophiles such as acetylacetone, aromatic and heterocyclic aldehydes in the alcoholic medium complete by formation of the corresponding hydrazones as a E-geometric isomers and s-trans/cis conformers with respect to the amide bond. In more severe conditions elimination of hydrazone fragments and retrocondensation of aminoazolophenylpropionyl residues in dihydroazolopyrimidinones have been observed.
The composition and structure of the hydrazones synthesized for the first time have been proven by data of elemental analysis, infrared spectroscopy (IR), nuclear magnetic resonance on protones (1H NMR) and mass spectra.
Virtual screening of the substances obtained carried out by using the PASS programme for 780 types of pharmacological action has shown that these compounds are advisable to test for the presence of their antibacterial and fungicidal properties. However, the experimental evaluation of the antimicrobial activity of N1-ylidene derivatives of 3-phenylpropanehydrazides performed on five museum strains of test cultures has revealed a weak activity against Staphylococcus aureus only in 3-(5-amіno-1H-1,2,4-triazol-1-yl)-N1 benzilіdene-3-phenylpropanehydrazide.
Downloads
References
- Bolton W. K., Abdel-Rahman E. Pimagedine: a novel therapy for diabetic nephropathy. Expert Opinion on Investigational Drugs, 2002, Vol. 11 (4), pp.565-574. doi: 10.1517/13543784.11.4.565
- Ivаnоvа О. V., Pоltоrаk V. V., Gоrbenkо N. I. Ekspеrimentalna i klіnіchna mеditsinа – Experimental and Clinical Medicine, 2004, No.4, pp.40-43.
- Pаt. 43676 (2001) Ukrаine. B. V., 2001, No.11.
- Ivanova O., Poltorak V., Gorbenko N., Lipson V. Abstracts. The 37th Annual Meeting of the EASD, Glasgow, 2001, A. 226.
- Ivanova O., Gorbenko N., Poltorak V., Gladkich A., Leshchenko Z. Antiatherogenic effect of new antioxidant L-2264 in diabetic rabbits, Diabetologia, 2004, Vol. 47, Suppl. 1, P. A 278.
- Lіpsоn V. V., Pоltоrаk V. V., Ivаnоvа О. V., Kаrnоzhits`kа Т. М., Svitlychna N. V., Shirоbоkоvа М. G., Vоrоbiоvа N. P. Аktuаl`nі prоblemy sintezu i stvоrеnnya novykh biоlоgіchnо аktyvnykh spоluk tа fаrmаtsеftychnykh prеpаrаtіv: Теzy dоpovidei Nаtsіоnаl`nоi nаukоvо-tеkhnіchnоi kоnfеrеntsіi z mіzhnаrоdnоyu uchаstyu (Actual Problems of Synthesis and Creation of New Biologically Active Compounds and Pharmaceuticals: Abstracts of the National Science and Technology Conference with International Participation), Lvіv, 2008, p.84.
- Lipsоn V. V., Dеsеnkо S. M., Оrlоv V. D., Shishkin О. V., Shirоbоkоvа М. G., Chеrnеnkо V. N., Zinоv`еvа L. I. Khimiya geterotsiklicheskikh soedinenii – Chemistry of Heterocyclic Compounds, 2000, No.11, pp.1542-1549.
- Lipsоn V. V., Dеsеnkо S. M., Оrlоv V. D., Kаrnоzhitskаya Т. М., Shirоbоkоvа М. G. Khimiya geterotsiklicheskikh soedinenii – Chemistry of Heterocyclic Compounds, 1999, No.5, pp.664-668.
- Lipsоn V. V., Оrlоv V. D., Dеsеnkо S. M., Shishkina S. V., Shishkin О. V., Shirоbоkоvа М. G. Khimiya geterotsiklicheskikh soedinenii – Chemistry of Heterocyclic Compounds, 2000, No.9, pp.1190-1196.
- Lipsоn V. V. Azoloazynovi systemy z chastkovo gidrogenizovanym azynovym frаgmеntom (Аvtоrеfеrаt dysеrtаtsіi … dоktоrа khіmіchnykh nаuk) – Azoloazine systems with partially hydrogenated azine fragment (Synopsis of the dissеrtаtion … of Doctor of Chemical Sciences). Kharkov, 2007, 33 p.
- Desenko S. M., Lipson V. V., Shishkin O. V., Komykhov S. A., Orlov V. D., Lakin S. E., Kuznetsov V. P., Meier H. Cyclocondensation of 3-amino-1,2,4-triazole with substituted methyl cinnamates, Journal of Heterocyclic Chemistry, 1999, Vol. 36, pp.205-208.
- Lide D. R. (ed.). Handbook of chemistry and physics. London, CRC Press, 1994, 324 p.
- Kuodis Z., Rutavičius A., Matijoška A., Eicher-Lorka O. Synthesis and isomerism of hydrazones of 2-(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-ylthio) acetohydrazide, Central European Journal of Chemistry, 2007, Vol. 5, pp.996-1006.
- Patorski P., Wyrzykiewicz E., Bartkowiak G. Synthesis and Conformational Assignment of N-(E)- Stilbenyloxymethylenecarbonyl-Substituted Hydrazones of Acetone and o-(m- and p-) Chloro- (nitro-) benzaldehydes by Means of 1H and 13C NMR Spectroscopy, Journal of Spectroscopy, 2013, Vol. 2013, Article ID 197475, 12 p.
- Palla G., Predieri G., Domiano P. Conformational behaviour and E/Z isomerization of N-acyl and N-aroylhydrazones, Tetrahedron, 1986, Vol. 42, pp.3649-3654.
- Litvinov I. A., Kataeva O. N., Ermolaeva L. V., Vagina G. A., Troepol’skaya T. V., Naumov V. A. Crystal and molecular structure of aroyl- and acetylhydrazones of acet- and benzaldehydes, Bulletin of the USSR Academy of Sciences, Division of Chemical Sciences (English Translation), 1991, Vol. 40,
- pp.62-67.
- Wyrzykiewicz E., Blaszczyk A. New isomeric N-substituted hydrazones of 2-, 3- and 4-pyridinecarboxaldehydes and methyl-3-pyridylketone, Journal of Heterocyclic Chemistry, 2000, Vol. 37, No.4, pp.975-981.
- www.ibmc.msk.ru/pass
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2014 National University of Pharmacy
This work is licensed under a Creative Commons Attribution 4.0 International License.
Authors publishing their works in the Journal of Organic and Pharmaceutical Chemistry agree with the following terms:
1. Authors retain copyright and grant the journal the right of the first publication of the work under Creative Commons Attribution License allowing everyone to distribute and re-use the published material if proper citation of the original publication is given.
2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal’s published version of the work (e.g., post it to an institutional repository or publish it in a book) providing proper citation of the original publication.
3. Authors are permitted and encouraged to post their work online (e.g. in institutional repositories or on authors’ personal websites) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (see The Effect of Open Access).