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The Pharmaceutical Society of Korea (대한약학회)
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Synthesis of New 2-Thiouracil-5-Sulfonamide Derivatives with Biological Activity

  • Fathalla, O.A. (Department of Medicinal Chemistry, National Research Centre) ;
  • Zaghary, W.A. (Pharmaceutical Chemistry Dept. Helwan University Faculty of Pharmacy) ;
  • Radwan, H.H. (Microbiology Dept. Helwan University Faculty of Pharmacy) ;
  • Awad, S.M. (Organic Chemistry Dept. Helwan University Faculty of Pharmacy) ;
  • Mohamed, M.S. (Organic Chemistry Dept. Helwan University Faculty of Pharmacy)
  • Published : 2002.06.01
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Abstract

2-Thiouracil-5-sulfonylchloride 1 reacted with a series of aromatic and heterocyclic amines to give 2a-j. The same compound 1 was reacted with a series of sulphonamides giving different sulphonamides of type 3a-e. On the other hand compound 1 was allowed to react with p-aminoacetophenone givining compound 4 which in turn was allowed to react with derivatives of alkyl thiosemicarbazides to give thiosemicarbazones of type 5a-e, also compound 4 was monobrominated to give compound 6 which in turn was reacted thiosemicarbazones of some aldehydes to give the corresponding thiazole derivatives 7a-f. In the same time compound 4 was reacted with a series of aromatic and heterocyclic aldehydes givining chalcones 8a-g (Claisen-Schemidt reaction). Also compound 4 was allowed to react with a series of aromatic and heterocyclic aldehydes, ethyl cyano acetate and/or malononitrile, and ammonium acetate giving pyridine derivatives 9a-d and 10a-e respectively. The biological effects of some of the new synthesized compounds was also investigated.

Keywords

References

  1. Abdel-Hamid, A. Z. and Fathalla, O. A. Effect of some new uracil derivatives on ehrlish ascites carcinoma cells. Egypt. J. Pharm. Sci., 34, 67-80 (1993)
  2. Afifi, A. Contribution to the chemical carcinogenesis in Xen-opus. "Ph.D. Thesis, UCL, Louvainha Neuve, Belgium, 90-91(1986)
  3. Bauer, A. W., Kirby, W. M. M., Sherris, J. C. and Turck, M. Antibiotic susceptibility testing by a standardized single disc method. Amer. J. Clin. Pathol., 45, 493-496 (1966)
  4. Beri A., Ross, L., Goodn, K. and Bakr, B, Potentionl anticancer agents (XL), synthesis of the B-anomer ef 9-(D-arabino-furanosyl)adinene. J. A. Chem. Soc., 82, 4585 (1960) https://doi.org/10.1021/ja01502a036
  5. Della, T., Scovill, J., Munslow, W. and Burchalter. 1B-D-Arabino-furanosyl cytosine and its derivatives and their biological activity. J. Med. Chem., 19,344 (1976) https://doi.org/10.1021/jm00224a032
  6. Ebeid, M. Y., Kamel, M. M., Nofal, Z. M., Gadalla, K. Z. and Abdou, W. A. M. Sythesis of some new-p-cinnamoylamino pyrimidines and other related products of possible Anti-Schistosomal activity. Egypt. J. Pharm. Sci., 32, 381-387 (1991)
  7. Essawy, S. and Wasfy, A. Convenient synthesis of heterocyclic compounds Bearing a succinimido moity. Egypt. J. Chem., 37, 283-293 (1994)
  8. Fathalla, O. A. Synthesis of some 1,3-dimethyluracil-5-sulphon-amide-p-derivatives with expected biological activity. Bulleten of Faculty of Science, Al-Azhar University, 3, No2 (Dec) 713-726 (1992)
  9. Fathalla, O. A. Synthesis of New Pyrazolo [1,5-a] Pyrimidine Derivatives Using 5-Aminouracil and Ketene Dithio Acital With expected Biological Activity. Arch. Pharm. Res., 22, 571-574 (1999) https://doi.org/10.1007/BF02975328
  10. Fathalla, O. A., Gad, H. S. M. and Maghraby, A. S. Synthesis of some new uracil-5-sulphonamide-p-phenyl derivatives and their effect on biomphalaria alexandrina snail's nucleoproteins. Arch. Pharm. Res., 23,128-138 (2000) https://doi.org/10.1007/BF02975501
  11. Giner Sorolla, Alfredo and Mediek. L. Synthesis and properties of 5-mercapto methyluracil and related derivatives. J. Med. Chem., 9, 79 (1966) https://doi.org/10.1021/jm00319a021
  12. Hamers, R. and Hamers, C. Synthesis by E-coli of a B-galadosidase-like protein under the influnce of thiouracil. Biochem. et Biophys. Acta 33,269-271 (1956)
  13. Lang, P. Antimetabolites of Nucliec acid metabolism, New York(1975)
  14. Mamesi, E. A. and Marciane, A. Action of thiouracil on the development of Lactobacillus species. Boll. Soc. Ital. Biol. sper., 37, 228-231 (1961)
  15. Maniates, T., Fritsch, E. F. and J. Sambrook CSH. Molecular cloning, Alaboratory Manual, 55-75 (1989)
  16. Moravek, J., Parkanyi, C. and Skoda, J. Antimicrobial effect of some pyrimidine analoges and related compounds. J. Gut, 3154-3162 (1980)
  17. Nakamura, M. and Jonsson, S. The effect of antimetabolites on the growth of Entamoebahistolyica. Archives of Biochemistry and Biophysics, 66,183-189 (1957) https://doi.org/10.1016/0003-9861(57)90549-0
  18. Sarkar, B. R. and Pathak, B. Synthesis of 4,4'-bithiazoles and 4-(2-thia-zolyl)aminoquinolines and their antiamobic activity. J. Ind. Chem. Soc., LXI, 151-153 (1984)
  19. Wyrzykiewicz-E, Bartkowiak, G. and Kedzia, B. Synthesis of anti-microbial properties of S-Substituted derivatives of 2-thiouracil. Farmaco, Poland., 48 (Jul), 979-988 (1993)