Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis of Certain Substituted Quinoxalines as Antimicrobial Agents (Part II)

  • Mohga.M.Badran (Department of Organic Chemistry, Faculty of Pharmacy, Cairo University) ;
  • Khaled.A.M.Abouzid (Department of Organic Chemistry, Faculty of Pharmacy, Cairo University) ;
  • M. H. M. Hussein (Department of Organic Chemistry, Faculty of Pharmacy, Cairo University)
  • Published : 2003.02.01
Download PDF
⟨ Previous Next ⟩

Abstract

Several fused triazolo and ditriazoloquinoxaline derivatives such as 1-aryl-4-chloro-[1,2,4]triazolo[4,3-a]quinoxalines (3a-d), 4-alkoxy[1,2,4]triazolo[4,3-a]quinoxalines (4a,b), 4-substituted-amino-[1,2,4] triazolo[4,3-a]quinoxalines (5a-h), 1-(aryl)-[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-thione (6), 4-(arylidenehydrazino )-1-phenyl-[1,2,4]triazolo[4,3-a]quinoxalines (10a-e) and [1,2,4]ditriazolo[4,3-a:3',4'-c]quinoxaline derivatives (11-13) have been synthesized and some of these derivatives were evaluated for antimicrobial and antifungal activity in vitro. It was found that compounds 3a and 9b possess potent antibacterial activity compared to the standard tetracycline.

Keywords

References

  1. Badr, M. Z. A, Mahgoub, S. A, Atla, F. M., and Moustafa, O. S., Chemistry and Cyclization Reactions of Pyrimidothienoquinoxaline Derivatives. Part-IV. J. Indian Chem. Soc., 74, 30-32 (1997)
  2. Campaigne, E. and Mclaughin, A R, Some Sulfur-containing Quinoxalines. J. Heterocyclic Chem., 20, 623-628 (1983) https://doi.org/10.1002/jhet.5570200323
  3. Campaigne, E. and Mclaughlin, A. R., Some 4-Alkyl s-Triazolo [4,3-a]quinoxalines. J. Heterocyclic Chem., 20, 781-782 (1983) https://doi.org/10.1002/jhet.5570200354
  4. Campiani, G. Aiello, F., Fabbrini, M. Morelli, E. Ramunno, A. Armaroli, S. Nacci, V. Garofalo, A. Greco, G. Novellino, E. Maga, G. Spadari, S. Bergamini, A. Ventura, L. Bongiovanni, B. Capozzi, M. Bolacchi, F. Marini, S. Coletta, M. Guiso, G., and Caccia, S., Quinoxalinylethylpyridylthioureas (QXPTs) as potent non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors. Further SAR studies and identification of a novel orally bioavailable hydrazine-based antiviral agent. J. Med. Chem., 44, 305-315 (2001)㈀硯⨀灯⨀䢤⨀က렋⨀⨀視⨀탡ﾖ⨀က塢⨀偢⨀婢⨀룥ﾖ⨀ကက䡣⨀䁣⨀䩣⨀飪ﾖ⨀က䀀롢⨀끢⨀멢⨀ﾖ⨀က਀⡢⨀⁢⨀⩢⨀ﾖ⨀က塥⨀健⨀ᣫﾖ⨀᠀ https://doi.org/10.1021/jm0010365
  5. Cheesman, G. W. H. and Rafiq, M., Quinoxaline and related compounds part VIII; Reactions of quinoxaline-2-(1H)ones and 2,3-(1H,4H)diones with hydrazines. J. Chem. Soc., (C), 452-456 (1971)
  6. Collins, C. H. Microbiological Methods. Butterworths, London, pp. 92, (1964)
  7. Dirlam, J. P., Presslitz, J. E., and Williams, B. J., Synthesis and antibacterial activity of some 3-[(alkylthio)methyl]quinoxaline 1-oxide derivatives. J. Med. Chem., 26, 1122-1126 (1983) https://doi.org/10.1021/jm00362a007
  8. El-Hawash, S. A., Habib, N. S., and Fanaki, N. H., Quinoxaline derivatives part II: Synthesis and antimicrobial testing of 1,2,4-triazolo[4,3-a]quinoxalines, 1,2,4-triazino[4,3-a]quinoxalines and 2-pyrazolylquinoxalines. Pharmazie, 54, 808-815 (1999)
  9. Krishnan, V. S. H., Narayan, G. K. A. S. S., Reddy-Sastry, C. V., Vemana, K., Trivedi, B. S., and Rao, B. E., Reaction of 3hydrazinoquinoxaline- 2-(1H)one with aromatic carbocyclic acids using diphenylphosphoryl azide: synthesis and antiallergic activity of s-triazolo[4,3-a]quionxaline-4-ones. Indian. J. Heterocyclic Chem., 3, 227-237 (1994)
  10. Kurasawa, Y., Muramatsu, M., Yamazaki, K., Okamoto, Y., and Takada, A, Synthesis of 3-(a-Chlorophenylhydrazono)heteroarylmethyl-2-oxo-1,2-dihydroquinoxalines with Antimicrobial Activity. J. Heterocyclic Chem., 23, 1387-1390 (1986) https://doi.org/10.1002/jhet.5570230526
  11. Rashed, N., El-Massry, A., El-Ashry, E. H., Amer, A., and Zimmer, H., A Facile Synthesis of Novel Triazoloquinoxalinones and Triazinoquinoxalinones. J. Heterocyclic Chem., 27, 691-694 (1990) https://doi.org/10.1002/jhet.5570270339
  12. Reddy-Sastry, C. V., Marwah, P., Marwah, A. K., and Rao, G.S., Synthesis and biological activity of some new N-arylcarbamoyl and arylthiocarbamoyl hydrazinoquinoxalin-2-ones. Indian. J. Chem., 28B, 885-891 (1989)
  13. Reddy-Sastry, C. V, Srinivasa-Rao, K., Krishnan, V. S. H., Rastogi, K., Jain, M. L., and Narayan, G. K. A. S. S., Synthesis and biological activity of some new tetrazolo-benzoxazines and bis-tetrazoloqinoxalines. Indian J. Chem., 29B, 396-403 (1990)
  14. Sarges, R., Howard, H. R., Browne, R. G., Lebel, L. A., Seymour, P. A., and Koe, B. K., 4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants. J. Med. Chem., 33, 2240-2254 (1990) https://doi.org/10.1021/jm00170a031
  15. Trivedi, B. K. and Bruns, R. F., [1,2,4]Triazolo[4,3-a]quinoxalin-4-amines: a new class of A1 receptor selective adenosine antagonists. J. Med. Chem., 31, 1011-1014 (1988) https://doi.org/10.1021/jm00400a021
  16. Vierfond, J. M., Legendre, L., Martin, C., Rinjard, P., and Miocque, M., Thieno- and isothiazolo(3,4-b)quinoxalines: synthesis, structure and pharmacological study. Eur. J. Med. Chem. Chim. Ther., 25, 251-255 (1990) https://doi.org/10.1016/0223-5234(90)90208-K
  17. Yoo, H. W., Suh, M. E., and Park, S. W., Synthesis and cytotoxicity of 2-methyl-4, 9-dihydro-1-substituted-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 2,3-disubstituted-5,10-pyrazino[2,3-g]quinoxalinediones. J. Med. Chem., 41, 4716-4722 (1998) https://doi.org/10.1021/jm970695n
  18. Youssef, A. F., Farag, H. H., Abdel-kader, M. A., and El-Gendy, M. A., Unsymetrical N,N-disubstituted anilines; Synthesis of $\alpha$(n-methylanilino)acetamide. Indian J. Chem., 14B, 279-286 (1976)