Synthesis, X-ray crystal structure study, and cytostatic and antiviral evaluation of the novel cycloalkyl-N-aryl-hydroxamic acids

Journal of Medicinal Chemistry

Volumn 48, Issue 3, 2005, Pages 884-887

  Barbarić, Monika ^a   Uršić, Stanko ^a   Pilepić, Viktor ^a   Zorc, Branka ^a   Hergold Brundić, Antonija ^b   Nagl, Ante ^c   Grdiša, Mira ^d   Pavelić, Krešimir ^d   Snoeck, Robert ^e   Andrei, Graciela ^e   Balzarini, Jan ^e   De Clercq, Erik ^e   Mintas, Mladen ^f  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b UNIVERSITY OF ZAGREB   (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

^d RUDER BO KOVI INSTITUTE   (Croatia)

^e REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^f UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; N HYDROXY N (4 CHLOROPHENYL) 3 CYCLOHEXYLPROPIONAMIDE; N HYDROXY N (4 CHLOROPHENYL)ADAMANTYLFORMAMIDE; N HYDROXY N (4 CHLOROPHENYL)CYCLOHEXYLACETAMIDE; N HYDROXY N (4 CHLOROPHENYL)CYCLOPENTYLPROPIONAMIDE; N HYDROXY N (4 CHLOROPHENYL)CYCLOPROPYLFORMAMIDE; N HYDROXY N PHENYLCYCLOHEXYLACETAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; BREAST CARCINOMA; CANCER CELL CULTURE; COLON CARCINOMA; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOMEGALOVIRUS; CYTOSTASIS; CYTOTOXICITY; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LARYNX CARCINOMA; NONHUMAN; PANCREAS CARCINOMA;

ACETAMIDES; ADAMANTANE; ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; CYTOMEGALOVIRUS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYDROXAMIC ACIDS; MICE; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 13444256026     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040878r     Document Type: Article

References (15)

1. Kehl, H. K. Chemistry and Biology of Hydroxamic Aids; Karger: Basel, 1982.
2. Bergeron, R. J. Synthesis and solution structure of microbial siderophores. Chem. Rev. 1984, 84, 587-602.
3. Hanessian, S.; Johnstone, S. Synthesis of hydroxamic esters via alkoxyaminocarbonylation of β-dicarbonyl compounds. J. Org. Chem. 1999, 64, 5896-5903.
4. Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Design and therapeutic application of matrix metalloproteinase inhibitors. Chem. Rev. 1999, 99, 2735-2776.
5. Wada, C. K.; Holms, J. H.; Curtin, M. L.; Dai Y.; Florjancic, A. S.; Garland, R. B.; Guo, Y.; Heyman, H. R.; Stacy, J. R.; Steinman, D. H.; Albert, D. H.; Bouska, J. J.; Elmore, I. N.; Goodfellow, C. L.; Marcotte, P. A.; Tapang, P.; Morgan, D. W.; Michaelides, M. R.; Davidsen, S. K. Phenoxyphenyl sulfone N-formyhydroxylamines (retrohydroxamates) as potent, selective, orally bioavailable matrix metalloproteinase inhibitors. J. Med. Chem. 2002, 45, 219-232.
6. Kolasa, T.; Stewart, A. O.; Brooks, C. D. W. Asymmetric synthesis of (R)-N-3-butyn-2-yl-N-hydroxyurea, a key intermediate for 5-lipoxygenase inhibitors. Tetrahedron: Asymmetry 1996, 7, 729-736.
7. Kerdesky, F. A. J.; Schmidt, S. P.; Holms, J. H.; Dyer, R. D.; Carter, G. W.; Brooks, D. W. Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroxyperoxy-6,8,11,14-eicosatetraenoic acid analogues. J. Med. Chem. 1987, 30, 1177-1186.
8. Odake, S.; Morikava, T.; Tsuchiya, M.; Imamura, L.; Kobashi, K. Inhibition of Helicobacter pylori urease activity by hydroxamic acid derivatives. Biol. Pharm. Bull. 1994, 17, 1329-1332.
9. Nandy, P.; Lien, E. J.; Avramis, V. I. Inhibition of ribonucleotide reductase by a new class of isoindole derivatives: drug synergism with cytarabine (Ara-C) and induction of cellular apoptosis. Anticancer Res. 1999, 19, 1625-1633.
10. Turbanti, L.; Cerbai, G.; Di Bugno, C.; Giorgi, R.; Garzelli, G.; Criscuoli, M.; Renzetti, A. R.; Subissi, A.; Bramanti, G. 1,2- Cyclomethylenecarboxylic monoamide hydroxamic derivatives. A novel class of non-amino acid angiotensin converting enzyme inhibitors. J. Med. Chem. 1993, 36, 699-707.
11. Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances, Synthesis, Patents, Applications, 4th ed.; Thieme: Stuttgart, 2001.
12. Pilepić, V.; Lovrek, M.; Vikić-Topić, D.; Uršić, S. An unusual case of carbon-nitrogen bond formation. Reactivity of C-nitroso group toward acyl chlorides. Tetrahedron Lett. 2001, 42, 8519-8522.
13. Hanessian, S.; Johnstone, S. Synthesis of hydroxamic esters via alkoxyaminocarbonylation of β-dicarbonyl compounds. J. Org. Chem. 1999, 64, 5896-5903.
14. Uršić, S.; Vréek, V.; Ljubas, D.; Vinković, I. Interaction of L-ascorbate with substituted nitrosobenzenes. Role of the ascorbate 2-OH group in antioxidant reactions. New J. Chem. 1998, 221-223.
15. Steinbrunn, G.; Fischer, A. N-hydroxy-halo-anilides as selective herbicides. Ger. Pat. 1,226,364; Oct 6, 1966; Chem. Abstr. 1967, 66, 28550r.