Synthesis, antimicrobial activity and conformational analysis of novel substituted pyridines: BF3-promoted reaction of hydrazine with 2-alkoxy pyridines

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 8, 2004, Pages 1845-1852

  Goda, Fatma E ^a   Abdel Aziz, Alaa A M ^b   Attef, Omer A ^c  

^a Mansoura University 35516   (Egypt)

^b MANSOURA UNIVERSITY   (Egypt)

^c AJMAN UNIVERSITY   (United Arab Emirates)

Author keywords

1H pyrazolo 3,4 b pyridines; Antimicrobial; Conformational analysis; Molecular mechanics; Pyridine; Semiemperical molecular orbital

Indexed keywords

ALCOHOL; ANTIINFECTIVE AGENT; CEFOTAXIME; CLOTRIMAZOLE; GENTAMICIN; HYDRAZINE DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; MALONONITRILE; NYSTATIN; PYRIDINE DERIVATIVE; SODIUM; STREPTOMYCIN;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANDIDA ALBICANS; CHEMICAL REACTION; CYCLIZATION; DRUG CONFORMATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; INFRARED SPECTROSCOPY; MICROANALYSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

ANTI-INFECTIVE AGENTS; HYDRAZINES; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; PYRIDINES;

EID: 1642420589     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.01.040     Document Type: Article

References (33)

1. Attia A., Michael M. Pharmazie. 37:1982;551.
2. Patel P., Koregaokar S., Shah M., Pareckh H. Il Farmaco. 1996;51.
3. Pourrias B., Dorme N., Pouvet P., Raynaud G. Therapie. 26:1971;859.
4. Yamada K., Takeda M., wakuua L., Itoh N., Ohtsuka H., Tsunashima A., Wakuua T.I. Chem. Pharm. Bull. 30:1982;3197.
5. Vìra K., Martin S., Karel W., Milan P., Jarmila K. Il Farmaco. 54:1999;666. and references therein.
6. Massimo P., Marco T., Daniela U., Giuseppe P., Pietro B., Fiorenzo P., Fabrizio Z. Il Farmaco. 55:2000;669.
7. Borgna P., Pregnolato M., Gamba I.A., Mellerio G. J. Heterocyclic Chem. 30:1993;1079.
8. Maria G.M., Valeria F., Daniele Z., Luciano V., Elena B. Il Farmaco. 56:2001;587. and references therein.
9. Sanna M.E., Wahid M.B., Laila I.I. Egypt J. Pharm. Sci. 39:1998;197.
10. Carla M.S.M., Carlos M.R.S.A., Carlos R.R., Eliezer J.B. Journal of Molecular Structure (Theochem). 579:2002;31.
11. Poreba K., Opolski A., Wietrzyk J., Kowalska M. Arch Pharm (Weinheim). 334:2001;219.
12. Poreba K., Opolski A., Wietrzyk J. Acta Pol. Pharm. 59:2002;215.
13. Bernardino A.M.R., Ferreira V.F., Fontoura G.A.T., Frugulhetti I.C.P.P., Lee M.M., Romeiro G.A., souza M.C.B., Sá P.M. J. Braz. Chem. Soc. 7:1996;273.
14. Kuo S.C., Huang L.J., Nakamura H. J. Med. Chem. 27:1984;539.
15. Arita, M.; Saito, T.; Sato, H.; Uehata, M.; Okuda, H. JP App. 91/255, 689; Chem. Abstr. 1993, 119, 95006u.
16. Sato, Y.; Shimogi, Y.; Kumakura, S.; Takagi, H. Ja pan, Kokai 75,151, 896; Appl. 74,61,149; Chem. Abstr. 1976, 84, 164771.
17. Sakurai A., Midoikawa N. Bull. Chem. Soc. Japan. 40:1967;1680.
18. Sakurai A., Midoikawa N. Bull. Chem.Soc. Japan. 41:1968;430.
19. Al-Arab M.M. J. Heterocycl. Chem. 26:1989;1665.
20. Al-Arab M.M., Tabba H.D., Abu-Yousef L.A., Marilyn M.O. Tetrahedron. 44:1988;7293.
21. Moustafa M.A., El-Emam A.A., Mashaley M.M. Chin.Pharm. J. 44:1992;37. and references therein.
22. More details about the effect of Lewis acids on the displacement of 2-alkoxypyridines with hydrazines and other nucleophiles, mechanistic study will be the subject of separate paper.
23. Abdel-Aziz A.A.-M., Matsunaga H., Kunieda T. Tetrahedron Lett. 42:2001;6565. and references cited therein.
24. Jain S.R., Kar A. Planta Med. 20:1971;118.
25. Jones, R. N.; Barry, A. L.; Gavan, T. L., Washington IIJA 1985, Manual of Clinical Microbiology 4th ed.; Lennette, E. H., Ballows, A., Hausler, W. J., Jr., Shadomy, H. J., Eds.; American Society for microbiology, Washington DC, pp 972-977.
26. Calculated logP (ClogP) values were computed by using the CS ChemDraw Ultra ver.7.0, November 27, 2001 by CambridgeSoft.Com, Cambridge, MA, USA.
27. Profeta S., Allinger N.L. J. Am. Chem. Soc. 107:1985;1907.
28. Allinger N.L. J. Am. Chem. Soc. 99:1977;8127.
29. CS Chem 3-D ultra™, Version 7.0 CambridgeSoft Corporation (2001).
30. Alvarez-Larena A., Piniella J.F. Victory, P, Borrell, J. I. and Vidal-Ferran, A., Zeitschrift für Kristallographie. 209:1994;773.
31. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. J. Am. Chem. Soc. 107:1985;3902.
32. Hyperchem version 5.1Hypercube, Inc.
33. Umezawa Y., Tsuboyama S., Takahashi H., Uzawa J., Nishio M. Tetrahedron. 55:1999;10047.