A New Class of Dihaloquinolones Bearing N′- Aldehydoglycosylhydrazides, Mercapto-1,2,4-triazole, Oxadiazoline and α-Amino Ester Precursors: Synthesis and Antimicrobial Activity

Journal of the Brazilian Chemical Society

Volumn 14, Issue 5, 2003, Pages 790-796

  Al Soud, Yaseen A ^a   Al Masoudi, Najim A ^b  

^a AL AL BAYT UNIVERSITY   (Jordan)

^b UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Antimicrobial activity; Hydrazides; Quinolones

Indexed keywords

(7 CHLORO 1 ETHYL 6 FLUORO 1,4 DIHYDRO 4 OXOQUINOLIN 3 YL) ALPHA AMINO ACETIC ACID ETHYL ESTER; 3 (4 AMINO 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL) 6 CHLORO 1 ETHYL 1,4 DIHYDRO 4 OXOQUINOLINE; 3 (4 AMINO 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL) 6,7 DICHLORO 1 ETHYL 1,4 DIHYDRO 4 OXOQUINOLINE; 6 CHLORO 1 ETHYL 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID HYDRAZIDE; 6 CHLORO 1 ETHYL 7 FLUORO 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID HYDRAZIDE; 6,7 DICHLORO 1 ETHYL 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID HYDRAZIDE; 6,7 DICHLORO 1 ETHYL 4 DIHYDRO 3 (5 THIOXO 1H 1,3,4 OXADIAZOL 3 YL) 4 OXOQUINOLINE; 7 CHLORO 1 ETHYL 6 FLUORO 1,4 DIHYDRO 4 OXOQUINOLINE 3 CARBOXYLIC ACID AZIDE; ANTIINFECTIVE AGENT; ESTER DERIVATIVE; HYDRAZIDE DERIVATIVE; MERCAPTO 1,2,4 TRIAZOLE; N' DEXTRO ALDEHYDOARABINOSYL(7 CHLORO LEVO ETHYL 6 FLUORO 1,4 DIHYDRO 4 OXOQUINOLIN 3 YL)CARBOHYDRAZIDE; N' DEXTRO ALDEHYDOGALACTOSYL(7 CHLORO LEVO ETHYL 6 FLUORO 1,4 DIHYDRO 4 OXOQUINOLIN 3 YL)CARBOHYDRAZIDE; N' DEXTRO ALDEHYDOMANNOSYL(7 CHLORO LEVO ETHYL 6 FLUORO 1,4 DIHYDRO 4 OXOQUINOLIN 3 YL)CARBOHYDRAZIDE; N' DEXTRO ALDEHYDORIBOSYL(7 CHLORO LEVO ETHYL 6 FLUORO 1,4 DIHYDRO 4 OXOQUINOLIN 3 YL)CARBOHYDRAZIDE; N' DEXTRO ALDEHYDOXYLOSYL(7 CHLORO LEVO ETHYL 6 FLUORO 1,4 DIHYDRO 4 OXOQUINOLIN 3 YL)CARBOHYDRAZIDE; OXADIAZOLINE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRECURSOR; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STAPHYLOCOCCUS AUREUS;

EID: 0242606195     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532003000500014     Document Type: Article

References (39)

1. For some recent reviews see: Chu, T. D. W.; Fernandez, P. B.; Adv. Drug Res. 1991, 21, 39; Wentland, M. P. In The New Generation of Quinolones; Siporin, C.; Heifetz, C. L.; Domagala, J. M., eds.; Maecel Dekker Inc.: New York, 1990, p. 1; Andriole, V. T.; The Quinolones; Academic Press: New York, 1988.
2. For some recent reviews see: Chu, T. D. W.; Fernandez, P. B.; Adv. Drug Res. 1991, 21, 39; Wentland, M. P. In The New Generation of Quinolones; Siporin, C.; Heifetz, C. L.; Domagala, J. M., eds.; Maecel Dekker Inc.: New York, 1990, p. 1; Andriole, V. T.; The Quinolones; Academic Press: New York, 1988.
3. For some recent reviews see: Chu, T. D. W.; Fernandez, P. B.; Adv. Drug Res. 1991, 21, 39; Wentland, M. P. In The New Generation of Quinolones; Siporin, C.; Heifetz, C. L.; Domagala, J. M., eds.; Maecel Dekker Inc.: New York, 1990, p. 1; Andriole, V. T.; The Quinolones; Academic Press: New York, 1988.
4. Chu, D. T. W.; Fernandez, P. B.; Antimicrob. Agents Chemother. 1989, 33, 131.
5. Smith, T. J.; Lewin, C. S. In The Quinolones; Anderiole, V. T., ed.; Academic Press: London, 1988, ch. 2.
6. Koga, H.; Itoh, A.; Murayama, S.; Suzue, S.; Ivikura, T.; J. Med. Chem. 1980, 23, 1358.
7. Lesher, G. Y.; Froelich, E. J.; Gruett, M. D.; Bailey, J. H.; Brundage, P. R.; J. Med. Chem. 1962, 5, 1963.
8. Wise, R.; Andrews, J. M.; Edwards, L. J.; Antimicrob. Agents Chemother. 1983, 23, 559.
9. Hayakawa, I.; Hiramitsu, T.; Tanaka, Y.; Chem. Pharm. Bull. 1984, 32, 4907.
10. Miyamoto, T.; Matsumoto, J.; Chiba, K.; Egawa, H.; Shibamori, K.; Minamida, A.; Nishimura, Y.; Okada, H.; Fuzita, M.; Hirose, T.; Nakano, J.; J. Med. Chem. 1990, 33, 1645.
11. Ueda, Y.; Shimizu, K.; Konno, M.; Matsumoto, F., eds.; The Quinolones; Life Sciences Publisher: Tokyo, 1991, p. 315.
12. El-Subbagh, H. I.; Abadi, A. H.; Al-Khawad, I. E.; Al-Rashood, K. A.; Arch. Pharm. Pharm. Med. Chem. 1999, 332, 19.
13. Yoshida, T.; Yamamatoo, Y.; Orita, H.; Kakiuchi, M.; Takahashi, Y.; Itakura, M.; Kado, N.; Mitani, K.; Yasuda, S.; Kato, H.; Itoh, Y.; Chem. Pharm. Bull. 1996, 44, 1074.
14. Nieto, M. J.; Alovero, F. d. L.; Manzo, R. H.; Mazzieri, M. R.; Eur. J. Med. Chem. 1999, 34, 209.
15. El-Abadelah, M. M.; Sabri, S. S.; Al-Ashqar, H. A.; Heterocycles 1997, 45, 255.
16. El-Abadelah, M. M.; Nazer, M. Z.; Sabri, S.; Khalid, S. M.; Voelter, N.; Geiger, M.; Z. Naturforschung 1997, 52b, 419.
17. El-Abadelah, M. M.; Nazer, M. Z.; El-Abadelah, N. S.; Meier, H.; Heterocycles 1995, 41, 2203.
18. Al-Masoudi, N. A.; Al-Soud, Y. A.; Eherman, M.; De Clercq, E.; Nucleos. Nucleot. 1998, 17, 2255.
19. de la Cruz, A.; Elguero, J.; Goya, P.; Matinez, A.; De Clercq, E.; J. Chem. Soc. Perkin Trans. 1 1993, 845.
20. da Matta, A. D.; Bernardino, A. M. R.; Romeiro, G. A.; de Oliveira, M. R. P.; de Souza, M. C. B. V.; Ferreira, V. F.; Nucleos. Nucleot. 1996, 15, 889.
21. Al-Masoudi, N. A.; Al-Soud, Y. A.; Al-Masoudi, I. A.; Sulfur Lett. 2000, 24, 13.
22. Al-Masoudi, N. A.; Al-Soud, Y. A.; Eherman, M.; De Clercq, E.; Bioorg. Med. Chem. 2000, 8, 1407.
23. Gootz, T. D.; Barrett, J. P.; Sutcliffe, J. A.; Antimicrob. Agents Chemother. 1990, 34, 8.
24. th. ICAAC, American Soc. for Microbiology, Washington D. C., 1991.
25. For references see: Ram, V. J.; Pandey, H. N.; Chem. Pharm. Bull. 1974, 22, 2778; Ram, V. J.; Pandey, H. N.; Agr. Biol. Chem. 1973, 37, 1465 and 2191.
26. For references see: Ram, V. J.; Pandey, H. N.; Chem. Pharm. Bull. 1974, 22, 2778; Ram, V. J.; Pandey, H. N.; Agr. Biol. Chem. 1973, 37, 1465 and 2191.
27. El-Khawass, S. M.; Habib, N. S.; J. Heterocyclic Chem. 1989, 26, 177.
28. Mir, I.; Siddiqui, M. T.; Comrie, A. M.; J. Chem. Soc. (Org.) 1971, 2798.
29. For biological activity of 1,3,4-oxadiazoles, see: Hill J. In The Comprehensive Heterocyclic Chem. II; Storr, R. C., ed.; Pergamon, Elsevier Science Ltd.: Oxford, 1996, ch. 4.06, p. 285; For biological activity of 1,2,4-triazoles, see: ch. 4.02, pp. 162, 163.
30. For biological activity of 1,3,4-oxadiazoles, see: Hill J. In The Comprehensive Heterocyclic Chem. II; Storr, R. C., ed.; Pergamon, Elsevier Science Ltd.: Oxford, 1996, ch. 4.06, p. 285; For biological activity of 1,2,4-triazoles, see: ch. 4.02, pp. 162, 163.
31. Oldfield, W.; GB pat. 1, 147, 336 1965 (CA 71: P49795t).
32. Kozello, I. A.; Khmelevskii, V. I.; Gasneva, A. Ya.; PCJOAU, Pharma. Chem. J. (Engl. Transl.) 1971, 5, 21 (CA 74: P99832k).
33. Young, R. W.; Wood, K. H.; J. Am. Chem. Soc. 1955, 77, 400.
34. Paintini, U.; Sørensen, O. W.; Ernst, R.; J. Am. Chem. Soc. 1982, 104, 6800.
35. Willker, W.; Leibfritz, D.; Kerssebaum, R.; Bermel, W.; Mag. Res. Chem. 1993, 31, 287.
36. Al-Masoudi, N. A.; Al-Soud, Y. A.; Geyer, A.; Spectroscopy Lett. 1998, 31, 287.
37. Bazile, S.; Moreau, N.; Bouzard, D.; Essiz, M.; Antimicrob. Agent Chemother. 1992, 36, 2622.
38. nd ed., American Society for Microbiology: Washington DC., 1993, p. 489.
39. Shen, L. L.; Mitcher, L. A.; Sharma, P. N.; O'Donnell, T. J.; Chu, D. W. T.; Cooper, C. S.; Pernet, T. A. G.; Biochemistry 1989, 28, 3886.