Izvestiya of Saratov University.

Chemistry. Biology. Ecology

ISSN 1816-9775 (Print)
ISSN 2541-8971 (Online)
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Language: 
Russian
Heading: 
Chemistry
Article type: 
Article
UDC: 
547.541.3,547.542.7
DOI: 
10.18500/1816-9775-2021-21-4-405-414
EDN: 
TMBQQ

Study of the relationship between geometric isomerism and biologically active properties of compounds

Autors: 
Gasanov Arif G., Institute of Petrochemical Processes of National Academy of Sciences of Azerbaijan
Ayyubov Ilgar G., Institute of Petrochemical Processes of National Academy of Sciences of Azerbaijan
Hajiyeva Gulsum E., Institute of Petrochemical Processes of National Academy of Sciences of Azerbaijan
Qurbanova Fidan S., Institute of Petrochemical Processes of National Academy of Sciences of Azerbaijan
Abstract: 

The results of the research in the field of studying the relationship of the geometric structure of organic compounds with their biological activity are presented. It has been shown that the stereospecific structure of organic and inorganic molecules can have a direct effect on the biologically active properties of substances. Among the known types of stereoisomerism (geometric and optical), this work summarizes the effect of various types of geometric isomerism on the bioactivity of compounds. In addition, the results of the authors’ own research are presented. In particular, the results of studying the antimicrobial and antifungal activity of hydroxyalkyl monoesters of norbornedicarboxylic acid depending on their stereoisomeric forms in relation to various pathogenic microorganisms are shown. The studies were carried out by the serial dilution method. As nutrient media, we used MPA pH 7,2–7,4 for bacteria and Sabouraud’s medium for fungi. The incubation time in a thermostat for bacteria was 18–24 hours at 37?C, for fungi 1–10 days at 28?C. It has been noted that the endo-isomers of the synthesized compounds have a higher antimicrobial and antifungal activity against grampositive (Staphylococcus aureus), gramnegative (Escherichia coli, Pseudomonas aeruginosa) bacteria, as well as yeast-like fungi of the genus Candida. Based on the obtained test reports, the synthesized compounds have been recommended for use as local antiseptic preparations.

Key words: 
stereoisomers
geometric isomerism
biological activity
monoesters of norbornene-dicarboxylic acid
endo-isomers
exo-isomers
antimicrobial drugs
antifungal activity
Reference: 
  1. Jagattaran D., Laxman R., Sastry R., Gowrisankar A. Effects of positional and geometrical isomerism on the biological activity of some novel oxazolidinones. Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, no. 2, pp. 337–343. https://doi.org/10.1016/j.bmcl.2004.10.073 
  2. Schmitz R., Skoog F., Playtis A., Leonar N. Cytokinins: Synthesis and Biological Activity of Geometric and Position Isomers of Zeatin. Plant Physiol., 1972, vol. 50, no. 6, pp. 702–705. https://doi.org/10.1104/pp.50.6.702 
  3. Makota M., Dubery I., Koorsen G., Steenkamp P. The Effect of Geometrical Isomerism of 3,5-Dicaffeoylquinic Acid on Its Binding Affi nity to HIV-Integrase Enzyme: A Molecular Docking Study. Evid Based Complement Alternat. Med., 2016, no. 10, pp. 4138–4142. https://doi.org/10.1155/2016/4138263 
  4. Orailo F. Comparative studies of the antioxidant effects of cis- and trans-resveratrol. Curr. Med. Chem., 2006, vol. 13, no. 1, pp. 87–98. DOI: 10.2174/092986706775197953 
  5. Ford B., Franks L., Radominska-Pandya A., Prather P. Tamoxifen Isomers and Metabolites Exhibit Distinct Affi nity and Activity at Cannabinoid Receptors: Potential Scaffold for Drug Development. PLoS One, 2016, vol. 11, no. 12, pp. 1672–1679. https://doi.org/10.1371/ journal.pone.016724
  6. Lal N., Berenjian L. Cis and trans isomers of the vitamin menaquinone-7: which one is biologically signifi cant. Applied Microbology and Biotechnology, 2020, vol. 104, no. 7, pp. 2765–2776. https://doi.org/10.1007/s00253-020-10409-1 
  7. Loventhal J., Vergel-Rivera G.M. Comparison of the activity of the cis and trans isomer of vitamin K1 in vitamin K-defi cient and coumarin anticoagulant-pretreated rats. Journal of Pharmacology and Experimental Therapeutics, 1979, vol. 209, no. 3, pp. 330–33. PMID: 439009 
  8. Mirosha C., Pathre S., Behrens J., Schauerhamer B. Uterotropic activity of cis and trans isomers of zearalenone and zearalenol. Applied Environment Microbiology, 1978, vol. 35, no. 5, pp. 986–987. https://doi.org/10.1128/ AEM.35.5.986-987.1978 
  9. Carvalho E., Pereira I. M., Mancini-Filho J. Chemical and physiological aspects of isomers of conjugated fatty acids. Food Science and Technology, 2010, vol. 30, no. 2, pp. 2061–2075. https://doi.org/10.1590/S0101-20612010000200002 
  10. Valenzuela A., Morgado N. Trans fatty acid isomers in human health and in the food industry. Biol. Res., 1999, vol. 32, no. 4, pp. 273–287. https://doi.org/10.4067/s0716-97601999000400007 
  11. Zhou W., Almeqdadt M., Xifaras M., Riddell I. The effect of geometric isomerism on the anticancer activity of the monofunctional platinum complex trans- [Pt(NH3)2(phenanthridine)Cl]NO3. Chem. Commun., 2018, vol. 54, no. 22, pp. 2788–2791. https://doi.org/10.1039/c8cc00393a 
  12. Tripathi K., Pandey N. D., Bahar A. Structure elucidation and antihepatotoxic activity of cis and trans-isomers of piperine isolated from dried fruits of Piper longum. International Journal of Pharmaceutical Sciences and Research, 2014, vol. 29, no. 1, pp. 251–258. https://doi.org/10.13040/IJPSR.0975-8232.6(1).251-58 
  13. Burn P., Crooks P., Ratcliffe B., Rees J. Sympathomimetic effects of exo- and endo-isomers of 2-aminobenzonorbornene in vitro and in vivo. Journal of Pharmacy and Pharmacology, 1980, vol. 32, no. 2, pp. 87–91. https://doi.org/10.1111/j.2042-7158.1980.tb12858.x
  14. Belanger P., Dufresne C. Preparation of exo-6-benzylexo-2-(m-hydroxyphenyl)-l-dimethylaminomethylbicyclo[2.2.2.]~tane. A non-peptide mimic of enkephalins. Canadian Chem. Journal, 1986, vol. 64, pp. 1514–1520. https://doi.org/10.1139/v86-248 
  15. Angst M., Mueller C., Lanjer G., Jans P. Response of Scolytus multistriatus (Coleoptera: Scolytidae) to alpha- and delta-multistriatin in Switzerland. Journal of Chemical Ecology, 1982, vol. 8, no. 11, pp. 1345–1352. https://doi.org/10.15287/afr.2014.196 
  16. Pavelyev R. S., Gnevashev S. G., Vafi na R. M., Gnezdilov O. I. Synthesis and antimycotic properties of hydroxy sulfides derived from exo- and endo-4-phenyl-3,5,8- trioxabicyclo[5.1.0]octanes. Mendeleev Commun., 2012, vol. 22, pp. 127–128. https://doi.org/10.1016/j.mencom.2012.05.003 
  17. 17. Pat. RU2591042C1, 2015 Sposob polucheniya endo- i ekzo-izomerov 2-(6’-chlorpiridin-3’-il)-7-azabitsiklo[2.2.1] heptana [Metod for producing endo- and exoisomers of 2-(6'-chloropyridin-3'-yl)-7-azafi cyclo[2,2,1]heptane] / Kazakov P. V., Lukashov O. I., Mairzabekova N. S., Vlasov M. I. 
  18. Gasanov A. G., Mamedov E. G., Ayyubov I. G., Qurbanova M. M. Stereoselective synthesis of acidic 2-oxyalkyl ethers of norbornenedicarboxylic acid on thw basis of conjugated cyclodienes of pyrolysis C5 fraction and investigation of their biological activity. Processes of Petrochemistry and Oil Refi ning, 2004, no. 1, pp. 57–60. 
  19. Gasanov A. G., Mamedov E. G., Ayyubov I. G., Guseynov N. S. The esters of mono- and dicarboxylic acids of bicycle(2.2.1.)-hept-5-ene-series and their biological activity. Processes of Petrochemistry and Oil Refi ning, 2005, no. 2, pp. 19–22. 
  20. Mamedov E. G., Gasanov A. G., Ayyubov I. G., Babayeva R. Z. Asimmetricheskoe (4+2)-tsikloprisoedinenie sintez chiralnykh efi rov norbornenkarbonovykh kislot. Azerbaijan Chemical Journal, 2006, no. 1, pp. 124–128. 
  21. Gasanov A. G., Mamedov E. G., Ayyubov I. G., Babayeva R. Z. Stereo-and eantioselective synthesis of monoethers of bicyclic carboxylic acids. Processes of Petrochemistry and Oil Refi ning, 2006, no. 3, pp. 52–60.
Received: 
27.02.2021
Accepted: 
10.03.2021
Published: 
24.12.2021