Amino acid derivatives. Part I. Synthesis, antiviral and antitumor evaluation of new α-amino acid esters bearing coumarin side chain

Acta Pharmaceutica

Volumn 56, Issue 2, 2006, Pages 175-188

  Al Masoudi, Najim A ^a   Al Masoudi, Iman A ^b   Ali, Ibrahim A I ^c   Al Soud, Yaseen A ^d   Saeed, Bahjat ^b   La Colla, Paolo ^e  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b UNIVERSITY OF BASRAH   (Iraq)

^c Suez Canal University   (Egypt)

^d AL AL BAYT UNIVERSITY   (Jordan)

^e UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Amino acids; Antitumor activity; Antiviral activity; Coumarin

Indexed keywords

2 (2H 1 BENZOPYRAN 2 ONE 7 YLOXY)ACETIC ACID; AMINO ACID DERIVATIVE; BENZYL 2 [2 (2 (2H BENZOPYRAN 2ON 7 YLOXY)ACETYLAMINO) 3 (2,3,4,6 TETRA O ACETYL ALPHA DELTA GLUCOPYRANOS 1 YLOXY)]PROPANOATE; BENZYL 2[2 (2 (2H BENZOPYRAN 2 ON 7 OXYL)ACETYLAMINO] 3 (2,3:4,6 DI O ISOPROPYLIDENE ALPHA DELTA MANNOFURANOS LEVO YLOXY)]PROPANOATE; COUMARIN; ESTER DERIVATIVE; METHYL 2 (2H 1 BENZOPYRAN 2 ONE 7 YLOXY)ACETATE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CD4+ T LYMPHOCYTE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; LEUKEMIA; PHYSICAL CHEMISTRY; TUMOR CELL LINE;

EID: 33645540887     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. G. Feuer, The Metabolism and Biological Actions of Coumarins, in Progress in Medicinal Chemistry (Eds. G. P. Ellis and G. B. West), Vol. 10, North-Holland and Publishing Company, New York 1974, pp. 85.
2. K. Padmawinata, Isolation and identification of cancer delaying compounds from the leaves of Giejera salicifolia, Acta Pharmacol. 4 (1973) 1-9.
3. K. G. Mann, The challenge of regulating anticoagulant drugs: focus on warfarin, Am. Heart J. 149 (2005) 495-536.
4. Y. Sato, Y. Kobayashi, T. Nagasaki, T. Oshima, S. Kumakura, K. Nakayama, H. Koike and H. Takagi, Studies on new β-adrenergic blocking agents I. Synthesis and pharmacology of coumarin derivatives, Chem. Pharm. Bull. 20 (1972) 905-917.
5. Y.-L. Chen, T.-C. Wang, N.-C. Chang, Y.-L. Chang, C.-M. Teng and C.-C. Tzeng, α-Methylene-γ-butyrolactones: synthesis and vasorelaxing activity assay of coumarin, naphthalene and quinoline derivatives, Chem. Pharm. Bull. 46 (1998) 962-965.
6. K. Furumi, T. Fujioka, H. Fujii, H. Okab, Y. Nakano, H. Matsunaga, M. Katano, M. Mori and K. Mihashi, Novel antiproliferative falcarindiol furanocoumarin ethers from the root of Angelica japonica, Bioorg. Med. Chem. Lett. 8 (1998) 93-96.
7. T. D. Bradshaw, M. C. Bibby, J. A. Double, I. Fichtner, P. A. Cooper, M. C. Alley, S. Donohue, S. F. Stinson, J. E. Tomaszewjski, E. A. Sausville and M. F. G. Stevens, Preclinical evaluation of amino acid prodrugs of novel antitumor 2-(4-amino-3-methylphenyl)benzothiazoles, Mol. Cancer Ther. 1 (2002) 239-246.
8. M. D. Wittman and J. F. Kadow, Amino acid derivatives of paclitaxel, U.S. Pat. 5,489,589, 6 Feb. 1996; ref. Chem. Abstr. 124 (1996) 289947a.
9. A. Casini, A. Scozzafava and C. T. Supuran, Cystein-modifying agents: A possible approach for effective anticancer and antiviral drugs, Environ. Health Perspect. 110 (2002) 801-806.
10. K.-L. Yu, W. E. Harte, P. Spinazze, J. C. Martin and M. M. Mansuri, Synthesis of 1,3-diamino-2-hydroxypropane derivatives as pseudosymmetric HIV protease inhibitors, Bioorg. Med. Chem. Lett. 3 (1993) 535-538.
11. V. Escuret, P. Parvaz, O. Hantz, M. A. Petit, C. Trepo and F. Zoulim, Study of the antiviral mechanism of action of ribavirin in the bovine viral diarrhea virus model, Gastroenterol. Clin. Biol. 26 (2002) 584-590.
12. J. R. Stangl, K. L. Carroll, M. Illichmann and R. Striker, Effect of antimetabolite immunosuppressants on Flaviviridae, including hepatitis C virus, Transplantation 77 (2004) 562-567.
13. B. S. Joshi, N. Viswanathan, C. L. Kaul and R. S. Grewal, Evaluation of some naturally occurring & synthetic coumarins for hypotensive activity, Indian J. Chem. 19B (1980) 495-499.
14. M. Birau and Z. Y. Wang, A dual-mode molecular switch based on a chiral binaphthol-coumarin compound, Tetrahedron Lett. 41 (2000) 4025-4028.
15. M. C. Alley, D. A. Scudiero, A. Monks, M. L. Hursey, M. J. Czerwinski, D. L. Fine, B. J. Abbott, J. G. Mayo, R. H. Schoemaker and M. R. Boyd, Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay, Cancer Res. 48 (1988) 589-601.
16. A. Asagarasu, T. Uchiyama and K. Achiwa, Design and synthesis of HIV protease inhibitor linked with binding unit to gp 120, Chem. Pharm. Bull. 46 (1986) 697-703.
17. S. Davis and A. K. Mohammed, Assessment of racemization n-alkylated amino acid derivatives during peptide coupling in a model dipeptide system, J. Chem. Soc. Perkin Trans, 1 1981, 2982-2990.
18. W. König and R. Geiger, Eine neue Methode zur Synthese von Peptiden: Hydroxybenzotriazolen, Chem. Ber. 103 (1970) 788-798.
19. R. M. Pennigton and R. R. Fischer, Dicyclohexylcarboiimide modification of bovine heart mitochondrial transhydrogenase, J. Biol. Chem. 256 (1981) 8963-8969.
20. A. Katritzky, K. Suzuki and S. K. Singh, N-Acylation in combinatorial chemistry ARKIVOC 2004, 12-35.
21. I. A. I. Ali, E. S. H. El-Ashry and R. R. Schmidt, Protection of hydroxyl groups with diphenyl and 9-fluorenyl trichloroacetimidates - effect on anomeric stereocontrol, Eur. J. Org. Chem. 2003, 4121-4131.
22. A. I. Ali, E. S. H. El-Ashry and R. R. Schmidt, Imidomethylation of C-nucleophiles using O-phthalimidomethyl trichloroacetimidate and catalytic mounts of TMSOTf, Tetrahedron 60 (2004) 4773-4780.
23. A. N. Brubaker, J. DeRuiter and W. L. Whitmer, Synthesis and rat lens aldose reductase inhibitory activity of some benzopyranones, J. Med. Chem. 29 (1986) 1094-1099.
24. M. J. Root and H. K. Steger, HIV-1 gp41 as a target for viral entry inhibition, Curr. Pharm. Design, 10 (2004) 1805-1825.
25. L. Ni, G. F. Gao and P. Tien, Rational design of highly potent HIV-1 fusion inhibitoryproteins: Implication for developing antiviral therapeutics, Biochem. Biophys. Res. Commun. 332 (2005) 831-836.
26. S. D. Young, S. F. Britcher, L. O. Tran, L. S. Payne, W. C. Lumma, T. A. Lyle, J. R. Huff, P. S. Anderson, D. B. Olsen, S. S. Carroll, D. J. Pettibone, J. A. Obrien, R. G. Ball, S. K. Balani, J. H. Lin, I. W. Chen, W. A. Schleif, V. V. Sardana, W. J. Long, V. W. Byrnes and E. A. Emini, Novel, highly potent non-nucleoside inhibitor of the human immunodeficiency-virus type-1 reverse transcriptase, Antimicrob. Agents Chemother. 39 (1995) 2602-2605.
27. H. Mitsuya, K. J. Weinhold, P. A. Furman, M. H. St. Clair, S. N. Lehrmann, R. C. Gallo, D. Bolognesi, D. W. Barry and S. Broder, 3′-Azido-3′-deoxythymidine (BW A509U), an antiviral agent that inihibits the ineffectivity and cytopathic effect of human T-lymphotropic virus type III/ lymphadenopathy-associates virus in vitro, Proc. Natl. Acad. Sci. USA 82 (1985) 7096-7100.
28. D. Durantel, N. Branza-Nichita, S. Carrouee-Durantel, T. D. Butters, R. A. Dwek and N. Zitzmann, Study of the mechanism of antiviral action of iminosugar derivatives against bovine viral diarrhea virus, J. Virol. 75 (2001) 8987-8998.