Synthesis and antiviral evaluation of some 5-N-arylaminomethyl-2- glycosylsulphanyl-1,3,4-oxadiazoles and their analogs against hepatitis A and herpes simplex viruses

Journal of Carbohydrate Chemistry

Volumn 27, Issue 6, 2008, Pages 357-372

  El Sayed, Wael A ^a   Fathi, Nahed M ^a   Gad, W A ^a   El Ashry, El Sayed H ^b,c  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b Alexandria University Faculty Of Science   (Egypt)

^c UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

Antiviral activity; Glycinoyl hydrazine; Hepatitis A virus (HAV); Herpes simplex virus type 1 (HSV 1); Oxadiazole; S Functionalized oxadiazole; Thioglycosides

Indexed keywords

HEPATITIS A VIRUS; HUMAN HERPESVIRUS 1; SIMPLEXVIRUS;

EID: 49449117210     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300802262778     Document Type: Article

References (34)

1. Zareen, A.; Maimoona, R.; Choudhary, M.I.; Supino, R.; Khan; Khalid, M.; Atta-ur-Rahman. Kinetics of novel competitive inhibitors of urease enzymes by a focused library of oxadiazoles/thiadiazoles and triazoles. Biophys. Res. Comm. 2004, 319, 1053-1063.
2. El-Azzouny, A.A.; Maklad, Y.A.; Bartsch, H.; Zaghary, W.A.; Ibrahim, W.M.; Mohamed, M.S. Synthesis and pharmacological evaluation of fenamate analogues: 1,3,4-oxadiazol-2-ones and 1,3,4-oxadiazole-2-thiones. Sci. Pharmac. 2003, 71, 331-356.
3. (a) Loetchutinat, C.; Chau, F.; Mankhetkorn, S. Synthesis and evaluation of 5-Aryl-3-(4-hydroxyphenyl)-1,3,4-oxadiazole-2-(3H)-thiones as P-glycoprotein inhibitors. Chem. Pharmaceut. Bull. 2003, 51, 728-730;
4. (b) Jakubkiene, V.; Burbuliene, M.M.; Mekuskiene, G.; Udrenaite, E.; Gaidelis, P.; Vainilavicius, P. Synthesis and antiinflammatory activity of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives. Farmaco 2003, 58, 323-328.
5. (a) Grover, G.; Kini, S.G. Synthesis and evaluation of new 1,3,4-oxadiazoles and 1,3,4-oxadiazole-2-thione derivatives of nalidixic acid as potential antibacterial and antifungal agents. Ind. J. Heterocyclic Chem. 2003, 12, 289-290;
6. (b) Sahin, G.; Palaska, E.; Ekizoglu, M.; Ozalp, M. Synthesis and antimicrobial activity of some 1,3,4-oxadiazole derivatives. Farmaco 2002, 57, 539-542.
7. Ali, A.E.; Omar, A.A.; Mohamed, A.O.; Johen, L. Synthesis, antimicrobial and anti-HIV-1 activity of certain 5-(1-admantyl)-2-substituted thio-1,3,4-oxaidazoles and 5-(1-admantyl)-3-substituted aminomethyl-1,3,4- oxadiazoline-2-thiones. Bioorg. Med. Chem. Lett. 2004, 12, 5107-5113.
8. Hassan Khan, M.T.; Choudhary, M.I.; Mohammed Khan, K.; Rani, M.; Atta-ur-Rahman. Structure-activity relationship of tyrosinase inhibitory combinatorial library of 2,5-disubsituted-1,3,4-oxadiazole analogues. Bioorg. Med. Chem. Lett. 2005, 13, 3385-3395.
9. Brajeswar, P.; Walter, K. S-, N-, and O-glycosyl derivatives of 2-acetamido-2-deoxyglucose with hydrophobic aglycons as potential chemotherapeutic agents and N-acetyl-β-glucosaminidase inhibitors. Carbohydr. Res. 1984, 126, 27-43.
10. Kuhn, C.S.; Lehmann, J.; Steck, J. Syntheses and properties of some photolabile β-thioglycosides. Potential photoaffinity reagents for β-glycoside hydrolases. Tetrahedron 1990, 46, 3129-3134.
11. Blanc-Muesser, M.; Vigne, L.; Driguez, H.; Lehmann, J.; Steck, J.; Urbahns, K. Spacer-modified disaccharide and pseudo-trisaccharide methyl glycosides that mimic maltotriose, as competitive inhibitors for pancreatic alpha-amylase: a demonstration of the "clustering effect. Carbohydr. Res. 1992, 224, 59-71.
12. (a) El Ashry, E.S.H.; Awad, L.F.; Atta, I.A. Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry. Tetrahedron 2006, 62, 2943-2998;
13. (b) Mereyala, H.B.; Gurijala, V.R. Use of 2-pyridyl-2-acetamido-3,4,6- tri-O-acetyl-2-deoxy-1-thio-β-D-gluco-pyranoside as a glycosyl donor and methyl iodide as an activator for the synthesis of 1,2-trans-linked saccharides. Carbohydr. Res. 1993, 242, 277-280;
14. (c) El Ashry, E.S.H.; Awad, L.F.; Abdel-Hamid, H.; Atta, I.A. Synthesis of interglycosidically S-linked 1-thio-oligosaccharides under microwave irradiation. J. Carbohydr. Chem. 2005, 24, 745-753;
15. (d) Defaye, J.; Gelas, J. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1991; Vol. 8E, 315-357.
16. Awad, O.M.E.; Attia, W.E. El Ashry, E.S.H. Comparative evaluation of D-glucosyl thioronium, glucosylthio heterocycles, Daonil, and insulin as inhibitors for hepatic glycosidases. Carbohydr. Res. 2004, 339, 469-476.
17. El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides: part 1. seco-Nucleosides. Adv. Heterocyclic Chem. 1996, 67, 391-438.
18. (a) El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides: part 2. diseco- Nucleosides. Adv. Heterocyclic Chem. 1997, 68, 1-88;
19. (b) El Ashry, E.S.H. El Kilany, Y. Acyclonucleosides: part 3. tri-, tetra-, and pentaseco-Nucleosides. Adv. Heterocyclic Chem. 1998, 9, 129-215.
20. El Ashry, E.S.H.; Rashed, N.; Shobier, A.H. Glycosidase inhibitors and their chemotherapeutic value. Part 1. Pharmazie 2000, 55, 251-262.
21. El Ashry, E.S.H.; Rashed, N.; Shobier, A.H. Glycosidase inhibitors and their chemotherapeutic value. Part 2. Pharmazie. 2000, 55, 331-348.
22. El Ashry, E.S.H.; Rashed, N.; Shobier, A.H. Glycosidase inhibitors and their chemotherapeutic value. Part 3. Pharmazie. 2000, 55, 403-415.
23. El Ashry, E.S.H.; Rashed, N.; Awad, L.F.; Ramadan, E.; Abdel-Mageed, S.M.; Rezki, N. Novel regioselective hydroxyl-alkylation of 4,5- diphenylimidazole-2-thione and a competitive intramolecular ring closure of the S-hydroxyalkyl-imidazoles to imidazo[2,1-b]thiazines and thiazoles. Role of catalyst, microwave irradiation, and solid support. Nucleosides Nucleotides Nucleic Acids 2007, 26, 423-435.
24. El Ashry, E.S.H.; Kassem, A.A.; Abdel-Hamid, H.; Louis, F.F.; Khattab, Sh.A.N.; Aouad, M.R. Novel regioselective formation of S- and N-hydroxyl-alkyls of 5-(3-chlorobenzo[b]thien-2-yl)-3-sulfanyl-4H-1,2,4-triazole and a facile synthesis of triazolo-thiazoles and thiazolo-triazoles. Role of catalyst and microwave. Nucleosides Nucleotides Nucleic Acids 2007, 26, 437-451.
25. El Ashry, E.S.H.; Kassem, A.A.; Abdel-Hamid, H.; Louis, F.F.; Khattab, Sh.A.N.; Aouad, M.R. Novel glycosylation of 5-(3-Chlorobenzo[b]thien-2-yl)-4H-1, 2,4-triazole-3-thiol, regioselectivity, role of catalyst and MW irradiation. J. Carbohydr. Chem. 2007, in press.
26. El Ashry, E.S.H.; Rashed, N.; Ibrahim, E.S.I. Strategies of synethtic methodologies for constructing b-mannosidic linkage. Curr. Org. Synth. 2005, 2, 175-213.
27. Ibrahim, Y.A.; Abbas, A.A.; Elwahy, A.H.M. Selective synthesis and structure of 2-N- and 3-S-glucosyl-1,2,4-triazoles of potential biological interest. Carbohydr. Lett. 1999, 3, 331-338.
28. Mansour, A.K.; Ibrahim, Y.A.; Eid, M.M.; Abdel-Hady, S.A.L. N-Glucosyl derivatives of some 1,2,4-triazines with tetra-O-acetyl-α- D-glucopyranosyl bromide. J. Carbohydr. Nucleosides Nucleotides 1981, 8, 81-99.
29. Mansour, A.K.; Ibrahim, Y.A.; Eid, M.M. Nucleoside derivatives of 1,2,4-triazine. Reaction of some derivatives of 1,2,4-triazine with tetra O-acetyl-α-D-glucopyranosyl bromide. Z. Naturforsch. 1976, 31b, 505-508.
30. Eid, M.M.; Abdel-Hady, S.A.L.; Ali, H.A.W. Reaction of some 1,2,4-triazines with acetobromoglucose. Arch. Pharm. 1990, 323, 243-245.
31. Ibrahim, Y.A. Facile approach for the selective glycosidation of cyclic asymmetric amides and thioamides. Carbohydr. Lett. 1996, 1, 425-432.
32. Mansour, A.K.; Ibrahim, Y.A.; Khalil, N.S.A.M. Selective synthesis and structure of 6-arylvinyl-2- and 4-glucosyl-1,2,4-triazines of expected interesting biological activity. Nucleosides Nucleotides Nucleic Acids 1999, 18, 2256-2283.
33. Tien, X.P.; Buu-Hot, N.D.; Xuosg. Tuberculostatic N-arylglycines and derivatives. J. Org. Chem. 1958, 23, 186-188.
34. Farag, R.S.; Shalaby, A.S.; El-Baroty, G.A.; Ibrahim, N.A.; Ali, M.A.; Hassan, E.M. Chemical and biological evaluation of the essential oils of different Melaleuca species. Phytotherapy Res. 2004, 18, 30-35.