Synthesis of 5-aryl-3-glycosylthio-4-phenyl-4H-1,2,4-triazoles and their acyclic analogs under conventional and microwave conditions

Journal of Carbohydrate Chemistry

Volumn 27, Issue 2, 2008, Pages 70-85

  El Ashry, El Sayed H ^a,b   Rashed, Nagwa ^a   Awad, Laila F ^a   Ramadan, El Sayed ^a   Abdel Maggeed, Somia M ^a   Rezki, Nagat ^a,c  

^a Alexandria University Faculty Of Science   (Egypt)

^b UNIVERSITY OF KARACHI   (Pakistan)

^c Ministry of High Education and Scientific Research   (Algeria)

Author keywords

1,2,4 Triazole; Alkylation; AM1 semi empirical calculation; Hydrogen bonding; Microwave irradiation (MWI); Thioglycoside

Indexed keywords

EID: 45849137859     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300802030795     Document Type: Article

References (45)

1. Varki, A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 1993, 3, 97-130.
2. Helenius, A.; Aebi, M. Intracellular functions of N-linked glycans. Science 2001, 291, 2364-2369.
3. Butters, T.D.; Dwek, R.A.; Platt, F.M. Inhibition of glycosphingolipid biosynthesis: application to lysosomal storage disorders. Chem. Rev. 2000, 100, 4683-4696.
4. El Ashry, E.S.H.; Ali, M.R. N-Acetylglucosamine-containing oligosaccharides. Pure Appl. Chem. 2007, 79, in press.
5. 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.
6. Vankar, Y.D.; Schmidt, R.R. Chemistry of glycosphingolipids-carbohydrate molecules of biological significance. Chem. Soc. Rev. 2000, 29, 201-216.
7. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Synthesis of glycopeptides containing carbohydrate and peptide recognition motifs. Chem. Rev. 2000, 100, 4495-4538.
8. Garegg, P.J. Thioglycosides as glycosyl donors in oligosaccharide synthesis. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
9. Schmidt, R.R.; Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method. Carbohydr. Chem. Biochem. 1994, 51, 21-124.
10. Paulsen, H. Advances in selective chemical synthesis of complex oligosaccharides. Angew. Chem. Int. Ed. Engl. 1982, 21, 155-160.
11. El Ashry, E.S.H.; Rashed, N.; Ibrahim, E.S.I. Strategies of synthetic methodology for constructing β-mannosidic linkage. Curr. Org. Synth. 2005, 2, 175-213.
12. El Ashry, E.S.H.; El Nemr, A. Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates; Blackwell: Oxford, UK, 2005.
13. El Ashry, E.S.H.; El-Nemr, A. Synthesis of mono- and di-hydroxylated prolines and 2-hydroxymethylpyrrolidines from non-carbohydrate precursors. Carbohydr. Res. 2003, 338, 2265-2290.
14. (a) El Ashry, E.S.H.; Awad, L.F.; Abdel-Hamid, H.; Atta, I.A. Microwave irradiation for accelerating the synthesis of thioglycosides. Syn. Commun. 2006, 36, 2769-2785;
15. (b) El Ashry, E.S.H.; Awad, L.F.; Abdel-Hamid, H.; Atta, I.A. Microwave-assisted organic synthesis of 3-(D-gluco-pentitol-1-yl)- 1H-1,2,4-triazole. Nucleosides Nucleotides Nucleic Acids 2006, 25, 325-335.
16. (a) Pornsuriyasak, P.; Demchenko, A.V. Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis. Tetrahedron Assym. 2005, 16, 433-439;
17. (b) Pornsuriyasak, P.; Gangadharmath, U.B.; Rath, N.P.; Demchenko, A.V. A novel strategy for oligosaccharide synthesis via temporarily deactivated S-thiazolyl glycosidase as glycosides as glycosyl acceptors. Org. Lett. 2004, 6, 4515-4518;
18. (c) Kamat, M.N.; Demchenko, A.V. Revisiting the armed-disarmed concept rationale: S-Benzoxazolyl glycosides in chemoselective oligosaccharide synthesis. Org. Lett. 2005, 7, 3215-3218.
19. Pastuch, G.; Wandzik, I.; Szeja, W. (5-Nitro-2-pyridyl) 1-thio-β-D-glucopyranoside as a stable and reactive acceptor. Tetrahedron Lett. 2000, 41, 9923-9926.
20. 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.
21. (a) El Ashry, E.S.H.; Rashed, N.; Shobier, A.H. Glycosidase inhibitors and their chemotherapeutic value. Pharmazie Part 1 2000, 55, 251-262;
22. (b) El Ashry, E.S.H.; Rashed, N.; Shobier, A.H. Glycosidase inhibitors and their chemotherapeutic value. Pharmazie Part 2 2000, 55, 331-348;
23. (c) El Ashry, E.S.H.; Rashed, N.; Shobier, A.H. Glycosidase inhibitors and their chemotherapeutic value. Pharmazie Part 3 2000, 55, 403-415.
24. Haikal, A.M.; El Ashry, E.S.H. Banoub. Synthesis and structural characterization of 1-(D-glycosyloxy)phthalazines. J. Carbohydr. Res. 2003, 338, 2291-2299.
25. (a) El Ashry, E.S.H.; Rashed, N.; Awad, L.F.; Abdel-Rahman, A.A.-H.; Rasheed, H.A. Synthesis of new 7-alkylated theophyllines by chemical modification of dyphylline. J. Chem. Res. (S) 2001, 2, 129-130;
26. J. Chem. Res. (M) 2001, 440-450;
27. (b) El Ashry, E.S.H.; Abdel Rahman, A.A.-H.; Rashed, N.; Rasheed, H.A. Homoacylovir analogues of unnatural bases and their activity against hepatitis B virus. Pharmazie 1999, 54, 893-897;
28. (c) El Ashry, E.S.H.; Abdel-Rahman, A.A.H.; Rashed, N.; Rasheed, H.A. Synthesis and anti-hepatitis B virus activity of some 2,3-dihydroxyprop-1-yl unnatural hetaryls. Arch. Pharm. Med. Chem. 1999, 332, 327-330.
29. (a) Tozkoparan, B.; Gokhan, N.; Aktay, G.; Yeşilada, E.; Ertan, M. Eur. J. Med. Chem. 2000, 34, 743;
30. (b) Chimirri, A.; Gitto, R.; Quartarone, S.; Orlando, V.; De Sarro, A.; De Sarro, G.B. Farmaco 2002, 57, 759;
31. (c) Akbarzadeh, T.; Tabatabai, S.A.; Khoshnoud, M.J.; Shafaghi, B.; Shafiee, A. Biooorg. Med. Chem. 2003, 11, 769;
32. (d) Rollas, S.; Kalyoncuoglu, N.; Sur-Altiner, D.; Yegenoglu, Y. Pharmazie 1993, 48, 308.
33. (a) El Ashry, E.S.H.; Ramadan, E.; Kassem, A.A.; Haggar, M. Microwave irradiation for accelerating organic reactions. Part 1: three, four and five membered heterocycles. Adv. Heterocyclic Chem. 2005, 88, 1-110;
34. (b) El Ashry, E.S.H.; Kassem, A.A.; Ramadan, E. Microwave irradiation for accelerating organic reactions. Part 2: six, seven fused and spiro heterocyclic ring Systems. Adv. Heterocyclic Chem. 2006, 90, 1-127;
35. (c) El Ashry, E.S.H.; Kassem, A.A. Account of microwave irradiation for accelerating organic reactions. Arkivoc 2006, ix, 1-15.
36. (a) Lidström, P.; Tierney, J.; Wathey, B.; Westman, J. Microwave assisted organic synthesis. Tetrahedron 2001, 57, 9225-9283;
37. (b) Hamelin, J.; Bazureau, J.P.; Texier-Boullet, F. In Microwave in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002; 253-293.
38. Stewart, J. J. P. MOPAC, Version 7.00, QCPE program.
39. Hoggart, E. Compounds related to thiosemicarbazide part II 1-benzoylthiosemicarbazides. J. Chem. Soc. 1949, 1163-1167;
40. Chem. Abstr. 1950, 40 2541i.
41. Tomayo, M.L.; Alonso, G.; Madrohero, R. No. 183 antituberculeux potentials 1-1-Aroyl-thiosemicarbazides. Bull. Soc. Chim. Fr. 1962, 1020-1023;
42. Chem. Abstr. 1962, 57, 9834d.
43. (a) Shah, M.H.; Mhasalkar, M.Y.; Patki, V.M.; Deliwala, C.V.; Sheth, U.K. New 1,2,4 (H) - triazole derivatives as diuretic agent. J. Pharm. Sci. 1969, 11, 1398-1401;
44. (b) Barryl, Y.; Joseph, J. Substituted triazole and related compounds. J. Med. Chem. 1966, 9, 42-46.
45. Tandon, M.; Barthwal, J.P.; Bhalla, T.N.; Bhargava, K.P. Synthesis & antiinflammatory activity of some new 3-(o-substituted phenyl)-4-substituted-phenyl-5-alkyl/alkenyl-mercapto-1H-1,2,4-triazoles. Indian J. Chem. 1981, 20B, 1017-1018.