DNA gyrase inhibitory and antimicrobial activities of some diphenic acid monohydroxamides

Journal of Medicinal Chemistry

Volumn 40, Issue 20, 1997, Pages 3292-3296

  Ohemeng, Kwasi A ^a   Podlogar, Brent L ^a   Nguyen, Van N ^a   Bernstein, Jeffrey I ^a   Krause, Heather M ^a   Hilliard, Jamese J ^a   Barrett, John F ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [4 [(N HYDROXY 2' CARBOXY 2 BIPHENYLCARBOXAMIDO)ETHYLIDENE]PHENYL] 4 PHENYLPIPERAZINE; ANTIINFECTIVE AGENT; DNA TOPOISOMERASE (ATP HYDROLYSING); GYRASE INHIBITOR; N HYDROXY N [2 (3,4,5 TRIMETHOXYPHENYL)ETHYL] 2 (2 CARBOXYPHENYL)BENZAMIDE; NALIDIXIC ACID; POLYMYXIN B NONAPEPTIDE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BIOASSAY; CONTROLLED STUDY; DNA DRUG COMPLEX; DNA SUPERCOILING; DRUG SYNTHESIS; ENZYME INHIBITION; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MEMBRANE TRANSPORT; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; NONHUMAN;

ANTI-BACTERIAL AGENTS; BIPHENYL COMPOUNDS; DNA TOPOISOMERASES, TYPE II; ENZYME INHIBITORS; ESCHERICHIA COLI; HYDROXAMIC ACIDS; MODELS, CHEMICAL; MODELS, MOLECULAR;

EID: 0030842608     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9701583     Document Type: Article

References (29)

1. Remers, W. A.; Bear, S. Synthetic Antibacterial Agents, In Burger's Medicinal Chemistry and Drug Discovery. Volume 4: Therapeutic Agents, 5th ed.; Wolff, M. E., Ed.; John Wiley & Sons, Inc.: New York, 1997; pp 267-271 and references cited therein.
2. Dax, S. L. Antibacterial Chemotherapeutic Agents; Chapman & Hall: London, 1997; pp 298-345.
3. Lesher, G.; Forelich, E.; Gruett, M.; Bailey, J.; Brundage, R. 1,8-Naphthalene Derivative, A New Class of Chemotherapy Agents. J. Med. Chem. 1962, 5, 1063-1065.
4. Sato, K.; Matsuura, Y.; Inoue, M.; Une, T.; Osada, Y.; Ogawa, H.; Mitsuhashi, S. In Vitro and In Vivo Activity of DL-8280, A New Oxazine Derivative. Antimicrob. Agents Chemother. 1982, 22, 548-553.
5. Shen, L. L.; Mitscher, L. A.; Sharma, P. N.; O'Donnell, T. J.; Chu, D. W. T.; Cooper, C. S.; Rosen, T.; Pernet, A. G. Mechanism of Inhibition of DNA Gyrase by Quinolone Antibacterials: A Cooperative Drug-DNA Binding Model. Biochemistry 1989, 32, 3886-3894.
6. Schluter, G. Ciprofloxacin: Review of Potential Toxicologic Effects. Am. J. Med. 1987, 82 (Suppl. 4A), 91-93.
7. Akahane, K.; Sekiguchi, M. A.; Une, T.; Osada, Y. Structure-Epileptogenicity Relationship of Quinolones with Special Reference to Their Interaction with Gamma-aminobutyric Acid Receptor Sites. Antimicrob. Agents Chemother. 1989, 33, 1704-1708.
8. Lietman, P. S. Fluoroquinolone Toxicities. An Update, Drugs 1995, 49 (Suppl. 2), 159-163.
9. Gough, A. W.; Kasali, O. B.; Sigler, R. E.; Baragi, V. Quinolone Arthopathy-Acute Toxicity to Immature Articular Cartilage Toxicol. Pathol. 1992, 20 (3, Part 1), 436-450.
10. Ohemeng, K. A.; Schwender, C. F.; Fu, K. P.; Barrett, J. P. DNA Gyrase Inhibitory and Antibacterial Activity of Some Flavones I. Bioorg. Med. Chem. Lett. 1993, 3, 225-230.
11. (a) Henry, D. R.; Guner, O. F. Techniques for Searching Databases of Three-Dimensional (3D) Structures with Receptor-based Queries. Electron. Conf. Trends Org. Chem. 1996, CD-ROM; meeting date 1995, paper 44; Rzepa, H. S., Leach, C., Goodman, J. M., Eds.; Royal Society of Chemistry: Cambridge, U.K.
12. (a) Henry, D. R.; Guner, O. F. Techniques for Searching Databases of Three-Dimensional (3D) Structures with Receptor-based Queries. Electron. Conf. Trends Org. Chem. 1996, CD-ROM; meeting date 1995, paper 44; Rzepa, H. S., Leach, C., Goodman, J. M., Eds.; Royal Society of Chemistry: Cambridge, U.K.
13. (b) Moock, T. E.; Henry, D. R.; Ozkabak, A. G.; Alamgir, M. Conformational Searching in ISIS/3D Databases. J. Chem. Inf. Comput. Sci. 1994, 34 (1), 184-189.
14. Kiely, J.; Huang, S.; Gambino, L.; Solomon, M. Biphenyl Dicarboxylic Acid Monoamides, New Gyrase Inhibiting Antimicrobial Agents. Abstr. 1988 ICAAC 1988, #1018.
15. Ohemeng, K. A.; Appolina, M.; Nguyen, V. N.; Schwender, C. F.; Singer, M.; Steber, M.; Ansell, J.; Argentieri, D.; Hageman, W. Synthesis and 5-Lipoxygenase Inhibitory Activities of Some Novel 2-Substituted-5-benzofuran Hydroxamic Acids. J. Med. Chem. 1994, 37, 3663-3667.
16. Borch, R. F.; Bernstein, M. D.; Durst, H. D. The Cyanohydridoborate Anion as a Selective Reducing Agent. J. Am. Chem. Soc. 1971, 93, 2897-2904.
17. Domagala, J. M.; Hanna, L. D.; Heifetz, C. L.; Hutt, M. P.; Mich, T. F.; Sanchez, J. P.; Solomon, M. New Structure Activity Relationships of Antibacterial 6,7- and 7,8-Disubstituted 1-Alkyl-1,4-dihydro-4-oxoquinolone-3-carboxylic Acids. J. Med. Chem. 1986, 29, 394-404.
18. Barrett, J. F.; Bernstein, J. I.; Krause, H. M.; Hilliard, J. J.; Ohemeng, K. A. Testing Potential Gyrase Inhibitors of Bacterial DNA Gyrase: A Comparison of the Supercoiling Inhibition Assay and "Cleavable Complex" Assay. Anal. Biochem. 1993, 224, 313-317.
19. Barrett, J. F.; Gootz, T. D.; McGuirk, P. R.; Farrell, C. A.; Sokolowski, S. A. Use of In Vitro Topoisomerase II Assays for Studying Quinolone Antibacterial Agents. Antimicrob. Agents Chemother. 1989, 33, 1697-1703.
20. ISIS 2.01 Database Searching Software; Molecular Design, Ltd., San Leandro, CA.
21. Achari, A.; Neidle, S. Nalidixic acid. Acta Crystallogr., Sect. B 1976, B32 (2), 600-602.
22. Wiley, R. A.; Rich, D. H. Peptidomimetics Derived from Natural Products. Med. Res. Rev. 1993, 3, 327-384.
23. 50 of 96 μg/mL in our enzyme assay.
24. Viljanen, P.; Vaara, M. Susceptibility of Gram-negative Bacteria to Polymyxin B Nonapeptide. Antimicrob. Agents Chemother. 1984, 25 (6), 701-705.
25. SYBYL Molecular Modeling System (version 6.22); TRIPOS Associates, St. Louis, MO.
26. Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 8, 892-1012.
27. Dewar, M. J. S.; Zoebish, E. G.; Healy, E. F.; Stewart, J. J. P. AMI: A New General Purpose Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
28. SPARTAN 4.0; Wavefunction, Inc.: Irvine, CA, 1995.
29. Mizuuchi, K.; Mizuuchi, M.; O'Dea, M. H.; Geliert, M. Cloning and Simplified Purification of Escherichia coli DNA Gyrase A and B Proteins. J. Biol. Chem. 1984, 259 (14), 9199-9201.