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Information × Registration Number 0206U004834, 0103U001222 , R & D reports Title New biologically active substances on the basis of synthetic muramylpeptides and natural triterpene glycosides. popup.stage_title Head Chirva Vasily Yakovlevich, Registration Date 22-03-2006 Organization National Taurida V.Vernadsky University popup.description2 Subject of the scientific study were: - Glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (muramyldipeptide, MDP). - Methods of synthesis and reactivity of 2-alkoxy-glyco-[2,1-d]-2-oxazolines. Synthesis of the necessary key derivatives to obtain muramylpeptides using 2-alkoxy-glyco-[2,1-d]-2-oxazolines. Synthetic scheme for obtaining of oligomer MDP analogues. A new MDP dimer analogue having fixed anomeric center configuration. - Triterpene glycosides of Tetrapanax papyriferum and stem bark of Kalopanax septemlobum. The aim of investigation:- To synthesize new (-glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (muramyldipeptide, MDP) with arylalkyl and alkylalicyclic aglycons for a search of immunoactive compounds. To test an action of these muramyldipeptide glycosides on protective antibacterial resistance of mice. - Synthesis and characteristic of 2-alkoxy-glyco-[2,1-d]-2-oxazolines varied in 2-oxyalkyl substituent nature. - Development of glycosylation method based on using of the synthesized glycooxazolines, evaluation of effectiveness and stereoselectivity of the obtained oxazoline derivatives interaction with alcohols. - Use the devised glycoside synthesis method for obtaining of the glycoside and oligosaccharide derivatives required to compose new muramylpeptides. - Creation of new potentially high active muramylpeptides by oligomerization of MDP 1,2-trans-glycosides using the synthetic scheme that involves directs linking of monomer glycopeptide fragments. - Search of new sources of triterpene glycosides having potential bioactivity. The result of research:- New glycosyl derivatives of MDP were synthesized. Investigation of stimulation of mice antibacterial resistance to Staphylococcus aureus by MDP glycosides found out the best protective effect for (-tolyl-MDP. - It was worked out a new synthetic scheme of the MDP oligomer analogue obtaining without use of the spacer fragments. A new dimer muramylpeptide having fixed anomeric center configuration was synthesized. For the first time 2-alkoxy-glyco-[2,1-d]-2-oxazolines - speciments of the new class of oxazolines derivative of sugars - were obtained. It was ascertained the synthesized 2-isobutoxy- and 2-trichcloroethoxy-glyco-[2,1-d]-2-oxazolines are high effective glycosyl donors. The optimal glycoside synthesis conditions were clarified, it were studied relative reactivity of the synthesized oxazolines and glycosylation stereoselectivity. With the developed glycosyde synthesis method it was obtained the row of key semiproducts for muramylpeptides synthesis including new 1,2-trans-glycosaminides and disaccharides of N-acyl-D-glucosamine with (-(1®3) and (-(1®4) glycosyl bond. - It were separated from stem bark of Tetrapanax papyriferum, from leaves and stem bark of Kalopanax septemlobum the individual triterpene glycosides and their complete chemical structures were established. There are twelve of separated glycosides the new ones. The melting points are determined with a PTP device. The optical rotation was measured with a Polamat-A polarimeter. 1H-NMR spectra are received on Bruker WP-200 (200 MHz), Varian Geminy-200 (200 MHz), Varian VXR-300 (300 MHz) and Bruker WМ-500 (500 MHz) spectrometers. TLC on the Kieselgel 60-F254 (Merck) and Silufol UV-254 (Kavalier) plates. Column Chromatography was performed with Aldrich 70 - 230 mesh, Merck 240 - 400 mesh and L-40/100 (Lachema) silica gel. High protective activity of p-tolyl-MDP was elucidated. This compound can be recommended to further biological tests as immunostimulator. The results of the work can be used for the synthesis of new muramylpeptides with potential high bioactivity and for the synthesis of others bioactive nature molecules and their analogues having 2-amino-2-deoxysugars fragments. The study of biological properties of the new dimer muramylpeptide which was synthesized in course of fulfillment of this work, let us receive new data about influence of muramylpeptides oligomerization into their biological action. In the case the synthesized preparation show high level of bioactivity it may be used in medicine and veterinary science as a new perspective immunomodulator. The elaborated synthetic schemes will be used for the synthesis of oligomer muramylpeptides. Product Description popup.authors popup.nrat_date 2020-04-02 Close