Synthesis and biological activity of Hepta-O-acetyl-1-O- (2-chloro-3-phenyl thio propyl)-β-D-maltose
PDF

Keywords

Thioglycosides
maltose
Benzoyl peroxide
Phenylsulfonyl chloride
Biological activity

How to Cite

Tabatadze, L. ., Sidamonidze, N., Gulbani, D., & Iremashvili, D. (2021). Synthesis and biological activity of Hepta-O-acetyl-1-O- (2-chloro-3-phenyl thio propyl)-β-D-maltose. Georgian Scientists, 3(4), 1–8. https://doi.org/10.52340/gs.2021.11.01

Abstract

Carbohydrate derivatives are distinguished with wide range of biological activity which is proven by successful usage of preparations made of Carbohydrate based in different branches of pharmaceutical chemistry. As a result of research of Carbohydrate compounde, the relationship between unique structure and its chemical and biological properties has been studied. Input of bulk liphophilic adamantine moiety in the proved medications or biologically active molecule in most cases is improved molecule’s biological characteristic, drug’s lipopilycity and prolonged actin is enhanced, and at the same time toxicity and side negative effects is reduced.We studied the reactions of acetylaryl glycosides with phenylsulfonyl chloride in the presence of a benzoyl peroxide catalyst. A new sulfur-containing glucoside was synthesized: Hepta-O-acetyl-1-O-(2-chloro-3-phenyl thio propyl)-β-D-maltose. The bactericidal properties of β-O-(2-chloro-3-phenyl thio propyl)-D-maltose of the obtained product after deacetylation were studied. With the help of the com­­pu­ter program PASS (Prediction of Activity Spectra for Substance) onlaines were able to predict the range of activity of substances. The obtained result established correlations on bactericidal properties between biological activity and the intended biological activity. The structure of the synthesized compounds was determined by physico-chemical research methods.

 

https://doi.org/10.52340/gs.2021.11.01
PDF

References

Robert J. Ferrier; Radical-Mediated Brominations at Ring Positions of Carbohydrates January, Advances in Carbo¬hydrate Chemistry and Biochemistry 2010, 49(3):37-92.

Anna Czubatka-Bienkowska, Anna Macieja, Joanna Sarnik, Zbigniew J. Witczak, Tomasz Poplawski; The oxidative induction of DNA lesions in cancer cells by 5-thio-D-glucose and 6-thio-D-fructopyranose and their genotoxic effects. Part 3, Bioorganic & Medicinal Chemistry Letters, March 2017, 27(5): 1210-1214

Małgorzata Korycka-Machała, Anna Brzostek, Bozena Dziadek, Malwina Kawka, Tomasz Popławski, Zbigniew J. Witczak, and Jarosław Dziadek; Evaluation of the Mycobactericidal Effect of Thio-functionalized Carbohydrate Derivatives; J. Molecules 2017, 22, 812.

Nader Al Bujuq, Strategies for introducing sulfur atom in a sugar ring: synthesis of 5-thioaldopyranoses and their NMR data; Journal of Sulfur Chemistry, 2019, 40(6): 664-702

L.V. Tabatadze, N.G.Shengelia, M.N, Sidamonidze, T.N. Chipchiuri; Biological activity of 1,2-O-disaccharide products. Cha¬p¬ter from the book,V.1.Chemical and Technological Aspects of Biopolymers". 2020,58-69. ISBN 978-9941-25-790-2; www.Elibrary.sou.edu.ge

L.V. Tabatadze, N.N. Sidamonidze, D.J. Iremashvili; Synthesis, Research and Biological activity of Hepta-O-acetyl-1-O-(2-chloro-3-phenyl thio propyl)-β-D-lactose. Chapter from the book, V.1. "Chemical and Technological Aspects of Biopolymers". 2020, 18-26. www.Elibrary.sou.edu.ge

Lali V. Tabatadze, Neli N. Sidamonidze, Ema J. Churgulia, Natia G. Shengelia. SYNTHESIS AND BIO¬LO¬GICAL ACTIVITY OF 2,3,4,6-TETRA-O-ACETYL-1-O-(2CHLORO-3-PHENYL THIO PRO¬¬PYL¬)-β-D-GALAC¬TOPYRA¬NO¬SE. Chapter from the book - BLACK SEA SCIENTIFIC JOURNAL OF ACADEMIC RESEARCH, 2017, 49(06): 37-43; IARC Impact Factor 2.110, EESTI, TALLINN. http://sc-media.org/.

Evangelina Repetto, Carla Marino, M. Laura Uhrig, Oscar Varela; Two Straightforward Strategies for the Synthesis of Thiodisaccharides with a Furanose Unit as the Nonreducing End; European Journal of Organic Chemistry, 2008, I.3, pp.540-547.

Orianne Cholet, Alain He´naut, Serge Casaregola, and Pascal Bonnarme; Gene Expression and Biochemical Analysis of Cheese-Ripening Yeasts: Focus on Catabolism of L-Methio¬nine, Lactate, and Lactose; American Society for Microbiology. 2007, 73, 8. pp. 2561-2570

John A Sturman, Yong Y Lin, Tetsuo Higuchi & J H Fellman; N-Acetylneuramin Lactose Sulfate: A Newly Identified Nutrient in Milk. 1985, 19, pp. 216-219.

N.N. Sidamonidze, R.O. Vardiashvili, K.Z. Onashvili, L.V. Tabatadze; Synthesis and Bactericidal Properties Sulfur-Containing 1,2-Trans-Glycosides; Black Sea Scientific J. Of Academic Research. Eesti, Tallin 2018, 41, 0,3. pp. 35-44.

L.V. Tabatadze, N.N. Sidamonidze, R.O. Vardiashvili, K.Z. Onashvili. Synthesis and biological activity of 2,3,4,6-tetra-o-acetyl-1-O-(2-chloro-3-phenyl thio propyl)-β-D-Glucopyranose; "Annals of Agrarian Science; 2019, 17(3): 355-361. https://www.elsevier.com/journals/annals-of-agrarian-science

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...