Microwave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 1, 2010, Pages 214-221

  Ajani, Olayinka O ^a   Obafemi, Craig A ^b   Nwinyi, Obinna C ^a   Akinpelu, David A ^b  

^a Covenant University ^*  (Nigeria)

^b OBAFEMI AWOLOWO UNIVERSITY   (Nigeria)

Author keywords

3 Hydrazinoquinoxalin 2(1H) one; Antibacterial activity; Gram positive bacteria; Microwave irradiation

Indexed keywords

2 QUINOXALINONE 3 HYDRAZONE DERIVATIVE; 3 (2 CYCLOHEXYLIDENEHYDRAZINYL)QUINOXALIN 2 (1H) ONE; 3 (2 CYCLOPENTYLIDENEHYDRAZINYL)QUINOXALIN 2 (1H) ONE; 3 [2 (1,7,7 TRIMETHYLBICYCLO[2.2.1]HEPTAN 2 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (2 BROMOCYCLOHEXYLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (2 CHLOROCYCLOHEXYLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (2 METHYLCYCLOHEXYLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (2 OXOINDOLIN 3 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (5 BROMO 2 OXOINDOLIN 3 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (5 CHLORO 2 OXOINDOLIN 3 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (5 METHYL 2 OXOINDOLIN 3 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (ANTHRACEN 9 (10H) YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (BUTAN 2 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (PENTAN 3 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 (PROPAN 2 YLIDENE)HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 [1 (2 OXO 2H CHROMEN 3 YL)ETHYLIDENE]HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 [1 (6 BROMO 2 OXO 2H CHROMEN 3 YL)ETHYLIDENE]HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 [1 (6 CHLORO 2 OXO 2H CHROMEN 3 YL)ETHYLIDENE]HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 [2 [1 (6 METHYL 2 OXO 2H CHROMEN 3 YL)ETHYLIDENE]HYDRAZINYL]QUINOXALIN 2 (1H) ONE; 3 HYDRAZINOQUINOXALIN 2 (1H) ONE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

ANTI-INFECTIVE AGENTS; CANDIDA ALBICANS; GRAM-NEGATIVE BACTERIA; HYDRAZONES; MICROBIAL SENSITIVITY TESTS; MICROWAVES; QUINOXALINES;

POSIBACTERIA;

EID: 72049108891     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.10.064     Document Type: Article

References (50)

1. Rashed N., El Massry A.M., El Ashry E.-S.H., Amer A., and Zimmer H. J. Heterocycl. Chem. 27 (1990) 691
2. Rollas S., and Küçükgüzel S.G. Molecule 12 (2007) 1910
3. Rollas S., Gülerman N., and Edeniz H. Farmaco 57 (2002) 171
4. Imramovský A., Polanc S., Vinšová J., Kočevar M., Jampítek J., Rečková Z., and Kaustová J.A. Bioorg. Med. Chem. 15 (2007) 2551 2513
5. Janin Y. Bioorg. Med. Chem. 15 (2007) 2479
6. Dimmock J.R., Vasishtha S.C., and Stables J.P. Eur. J. Med. Chem. 35 (2000) 241
7. Lima P.C., Lima L.M., Silva K.C., Leda P.H., Miranda A.L.P., Fraga C.A.M., and Barreiro E.J. Eur. J. Med. Chem. 35 (2000) 187
8. Salgin-Göksen U., Gökham-Keleçi N., Göstal O., Köysal Y., Kiliçi E., Işik S., Aktay G., and Özalp M. Bioorg. Med. Chem. 12 (2004) 3149
9. Kalsi R., Shrimali M., Bhalla T.N., and Barthwal J.P. Ind. J. Pharm. Sci. 41 (2006) 353
10. Silva G.A., Costa L.M.M., Brito F.C.F., Miranda A.L.P., Barreiro E.J., and Fraga C.A.M. Bioorg. Med. Chem. 12 (2004) 3149
11. Savini L., Chiasserini L., Travagli V., Pellerano C., Novellino E., Consentino S., and Pisano M.B. Eur. J. Med. Chem. 39 (2004) 113
12. Bijev A. Lett. Drug Descrip. Discovery 3 (2006) 506
13. Loncle C., Brunel J.M., Vidal N., Dherbomez M., and Letourneux Y. Eur. J. Med. Chem. 39 (2004) 1067
14. Abdel-Aal M.T., El-sayed W.A., and El-ashry E.H. Arch. Pharm. Chem. Life Sci. 339 (2006) 656
15. El-Hawash S.A.M., Abdel W.A.E., and El-Dewellawy M.A. Arch. Pharm. Chem. Life Sci. 339 (2006) 14
16. Cocco M.T., Congiu C., Lilliu V., and Onnis V. Bioorg. Med. Chem. 14 (2005) 366
17. Capilla J., Serena C., Javier F., Ortoneda T., and Guarro J. Antimicrob. Agents Chemother. 47 (2003) 3976
18. Walcourt A., Loyevsky M., Lovejoy D.B., Gordeuk V.R., and Richardson D.R. Int. J. Biochem. Cell Biol. 36 (2004) 401
19. Fischer E. Ber. Deutsch. Bot. Ges. band 8 (1875) 589
20. Sridhar S.K., Saravanan M., and Ramesh A. Eur. J. Med. Chem. 36 (2001) 61
21. Sridhar S.K., and Ramesh A. Biol. Pharm. Bull. 24 (2001) 1149
22. Sarangapani M., and Reddy V.M. Ind. J. Pharm. Sci. 59 (1997) 105
23. Soliman F.S.G., Labouta I.M., and Stadlbauer W. Arch. Pharm. Chem. Sci. Ed. 13 (1985) 49
24. Cho C.S., Lim D.K., Hoe N.H., Kim T.J., and Shim S.C. Chem. Commun. 6 (2004) 104
25. Kappe T., Aigner R., Jobstel M., Hohengassner P., and Stadlbauer W. Heterocycl. Commun. 1 (1995) 341
26. Abd El-hafez O.M., El-khrisy E.D., Badria F., and Fathy A.D. Arch. Pharm. Res. 26 (2003) 686
27. Vicini P., Zani F., Cozzini P., and Daytchinova I. Eur. J. Med. Chem. 37 (2002) 553
28. Sridharan V., Perumal P.T., Avendaño C., and Menéndez J.C. Org. Biomol. Chem. 5 (2007) 1351
29. Küçükgüzel S.G., Mazi A., Sahin F., Ozturk S., and Stables J. Eur. J. Med. Chem. 38 (2003) 1005
30. Nayak N., Nag T.C., Satpathy G., and Ray S.B. Ind. J. Med. Res. 125 (2007) 767
31. Masunari A., and Tavares L.C. Bioorg. Med. Chem. 15 (2007) 4229
32. Kaatz G.W., McAleese F., and Seo S.M. Am. Soc. Microbiol. 49 (2005) 1857
33. Strahilevitz J., Truong-Bolduc Q.C., and Hooper D.C. Antimicrob. Agents Chemother. 49 (2005) 5051
34. Jensen L.B., Baloda S., Boye M., and Aerestrup F.M. Environ. Int. 26 (2001) 581
35. Wong K.K.Y., and Hancock R.E.W. J. Bacteriol. 82 (2000) 2402
36. Edoh D., and Alomatu B. Comparison African J. Sci. Technol. 8 (2007) 1
37. Lundin J.I., Dargatz D.A., Wagner B.A., Lombard J.E., Hill A.E., Ladely S.R., and Fedorka-Cray P.J. Food Borne Pathogen Dis. 5 (2008) 7
38. Kang J.H., and Lee M.S. J. Appl. Microbiol. 98 (2005) 1169
39. Kumar S., Kohlhoff S., and Valencia G. Int. J. Antimicrob. Agents 29 (2007) 740
40. Goldblatt D., and Thrasher A.J. Clin. Exp. Immunol. 122 (2000) 1
41. Dyatkina N.B., Roberts C.D., Keicher J.D., Dai Y., Nadherny J.P., Zhang W., Schmitz U., Kongpachith A., Fung K., Novikov A.A., Lou L., Velligan M., Khorlin A.A., and Chen M.S. J. Med. Chem. 45 (2002) 805
42. Lemriss S., Laurent F., Couble A., Casoli E., Lancelin J.M., Saintpierre B.D., Rafia S., Fassounane A., and Boiron P. Can. J. Microbiol. 49 (2003) 669
43. Kanamaru T., Nakano Y., Toyoda Y., Miyagawa K.I., Tada M., Kaisho T., and Nakao M. Antimicrob. Agents Chemother. 45 (2001) 2455
44. Ajani O.O., Obafemi C.A., Ikpo C.O., Ajanaku K.O., Ogunniran K.O., and James O.O. Int. J. Phys. Sci. 4 (2009) 156
45. Obafemi C.A., and Pfleiderer W. Helv. Chim. Acta 77 (1994) 1549
46. Cheeseman G.W.H., and Rafiq M. J. Chem. Soc., Sect. C 3 (1971) 452
47. Voet, D.; Voet, J. D. In Biochemistry 3rd ed.; 2004; pp 1341-1342. ISBN 0-471-19250-x (cloth).
48. Prescott L.M., Harley J.P., and Donald K.A. Microbiology. 6th ed. (2005), McGraw Hill
49. Russell A.D., and Furr J.R. J. Appl. Bacteriol. UK 43 (1977) 253
50. Okigbo R.N., and Ogbonnaya U.O. African J. Biotechnol. 5 9 (2006) 727