Synthesis and biological activity of 4-(4-hydroxybenzylidene)-2-(substituted styryl) oxazol-5-ones and their o -glucosides
Main Article Content
Keywords
Oxazolone, α - acetobromoglucose, decetylation, o -glucosides, antimicrobial and antifungal activity.
Abstract
The 4-(4-hydroxybenzylidene)-2-methyl oxazol-5-ones 1 treated with various aldehydes in the presence of acetic acid to form 4-(4-hydroxybenzylidene)-2-(substituted styryl) oxazol-5-ones 2a-i which were glucosylated by using α-acetobromoglucose as a glucosyl donor to affords 4-(4-o-β-d-tetra-o-acetyl- glucoxybenzylidene)-2-(substituted styryl) oxazol-5-ones 3a-i which was deacetylated by using Zinc acetate in absolute methanol to formed 4-(4-o-β-d-glucoxybenzylidene)-2-(substituted styryl) oxazol-5-ones 4a-i. Compounds showed good antimicrobial and antifungal activity.
References
2. Richard H.Wilys, Chem. Rev. 401-442 (1945).
3. Ignatius J.Turchi and Michael J.S. Dewar, Chem.Rev, 75, No-4, 389-437(1975).
4. For general discussion, See E.D. Bransome, Ed, “The Current status of liquid scintillation counting” Grune and Stratton, New York, N.Y. (1970); J.B.Birsks, “The Theory and Practice of Scintillation counting” Pergamon press, Oxford, (1964)
5. C.F.Laiborne; N.J.Liverton; K.T. Nguyen, Tetrahedron Letters, 39, 8939(1998).
6. U.G.Kang; H. Shechter, J. Am. Chem. Soc., 100, 651, (1978).
7. S.Sarshar; C.Zhang; E. J.Moran; S.Krane; J.C Rodrate; K.D.Benbatoul; R. Dixon; A.M.M. Mjalli, Bioorg. Med. Chem., 10, 2599 (2000).
8. S. C.Shilcrat; M. K.Mokhallalati; J.M.D.Fortunak; L. N. Pridgen, J.Org Chem., 62, 8449. (1997),
9. Y.Zung; P.Brokowich; Eu. J. Nat. Sci., 28, 1001(2000).
10. H.Lis, & N.Sharon; Eu. J .Biochem., 1, 218 (1993).
11. Goodman & Gillman, “The Pharmacological Basis of Therpeutics”, Tenth Edition, McGraw-Hill Medical Publishing Division (2000).
12. Essential Glucobiology, Cummings, R. Esko, J.Freeze.H; H.Harts.Eds; Cold Spring Harbor Laboratory Press: Plainview, NY (1999).
13. V.N.Ingle, K.M.Hatzade, V.S.Taile, P.K.Gaidhane and S.T.Kharche, J.Carbohydrate, Chem, 26, 107-123 (2007).
14. B. S.Fufniss; A.J.Hannaford; P.W.G.Smith; A.R. Tatchell, Vogel’s text book of Practical Organic Chemistry,5th Ed; Pearson Education(Singapore)Pte.Ltd. Delhi (2005).
15. P.T.Lewis; K.Wahala, Molecules, 2, 137-139(1998).
16. Y. Wang ; L.Li; Q.Wang; Y. Li,Synth.Commun., 31(22), 3423-27(2001).
17. V.K.Pandey & Meenal Tandon, Indian J.Chem. 40B, 527-529(2001).
Article Sidebar
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
All articles published in JPTCP are licensed under Copyright Creative Commons Attribution-NonCommercial 4.0 International License.