Antitumor agents. 172. Synthesis and biological evaluation of novel deacetamidothiocolchicin-7-ols and ester analogs as antitubulin agents

Journal of Medicinal Chemistry

Volumn 40, Issue 6, 1997, Pages 961-966

  Shi, Qian ^a   Verdier Pinard, Pascal ^b   Brossi, Arnold ^a   Hamel, Ernest ^b   McPhail, Andrew T ^c   Lee, Kuo Hsiung ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 O ACETYLDEACETAMIDOTHIOCOLCHICINE; 7 O BUTYRYLDEACETAMIDOTHIOCOLCHICINE; 7 O NICOTINOYLDEACETAMIDOTHIOCOLCHICINE; ANTINEOPLASTIC AGENT; COLCHICINE; COLCHICINE DERIVATIVE; DEACETAMIDOCOLCHICINE; DEACETAMIDOTHIOCOLCHICIN 7 OL; ISONICOTINOATE; THIOCOLCHICINE; THIOCOLCHICONE; UNCLASSIFIED DRUG;

ARTICLE; BURKITT LYMPHOMA; DRUG CONFORMATION; DRUG DESIGN; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MICROTUBULE ASSEMBLY;

EID: 0030946321     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960663k     Document Type: Article

References (27)

1. Fujioka, T.; Kashiwada, Y.; Okabe, H.; Mihashi K.; Lee, K. H. Antitumor Agents 171, Cytotoxicities of lobatosides B, C, D and E cyclic bisdesmosides isolated from Actinostemma lobatum maxim. Bioorg. Med. Chem. Lett., in press.
2. Boyé, O.; Brossi, A. Tropolonic colchicum alkaloids and allo congeners. In The Alkaloids; Brossi, A., Ed.; Academic Press, Inc.: New York, 1992; Vol. 41, pp 125-176.
3. Levy, M.; Spino, M.; Read, S. E. Colchicine: a state-of-the-art review. Pharmacotherapy 1991, 11, 196-211.
4. Yeh, H. J. C.; Chrzanowska, M.; Brossi, A. The importance of the phenyl-tropolone 'aS' configuration in colchicine's binding to tubulin. FEBS Lett. 1988, 229, 82-86.
5. (a) Andreu, J. M.; Timasheff, S. N. Interaction of tubulin with single ring analogues of colchicine. Biochemistry 1982, 21, 534-543;
6. (b) The interactions of tropolone with magnesium ions and tubulin. Biochim. Biophys. Acta 1982, 714, 373-377.
7. Sun, L.; McPhail, A. T.; Hamel, E.; Lin, C. M.; Hastie, S. B.; Chang, J. J.; Lee, K. H. Antitumor Agents. 139. Synthesis and biological evaluation of thiocolchicine analogs 5,6-dihydro-6(S)-(acyloxy- and 5,6-dihydro-6(S)-[(aroyloxy)methyl]-1,2,3-trimethoxy-9-(methylthio)-8H- cyclohepta[a]naphthalen-8-ones as novel cytotoxic and antimitotic agents. J. Med. Chem. 1993, 36, 544-551.
8. Sun, L.; Hamel, E.; Lin, C. M.; Hastie, S. B.; Pyluck, A.; Lee, K. H. Antitumor Agents. 141. Synthesis and biological evaluation of thiocolchicine analogs: N-acyl, N-aroyl, and N-(substituted benzyl)deacetylthiocolchicines as cytotoxic and antimitotic compounds. J. Med. Chem. 1993, 36, 1474-1479.
9. Shi, Q.; Verdier-Pinard, P.; Brossi, A.; Hamel, E.; Lee, K. H. Antitubulin Action of (+)-Thiocolchicine Prepared by Partial Synthesis. J. Med. Chem., submitted.
10. Prelog, V.; Helmchen, G. Basic principles of the CIP-system and proposals for a revision. Angew. Chem., Int. Ed. Engl. 1982, 21, 567-589.
11. Maity, S. N.; Ray, K.; Banerjee, A.; Mukhopadhyay, K.; Roychowdhury, S.; Chaudhuri, G. G.; Biswas, B. B.; Bhattacharyya, B. Role of B-ring of colchicine in its binding to tubulin. Indian J. Biochem. Biophys. 1988, 25, 585-589.
12. Kang, G. J.; Getahun, Z.; Muzaffar, A.; Brossi, A.; Hamel, E. N-acetylcolchinol O-methyl ether and thiocolchicine, potent analogs of colchicine modified in the C ring. Evaluation of the mechanistic basis for their enhanced biological properties. J. Biol. Chem. 1990, 265, 10255-10259.
13. Muzaffar, A.; Brossi, A.; Lin, C. M.; Hamel, E. Antitubulin effects of derivatives of 3-demethylthiocolchicine, methylthio ethers of natural colchicinoids, and thioketones derived from thiocolchicine. Comparison with colchicinoids. J. Med. Chem. 1990, 33, 567-751.
14. Burger, A. In Medicinal Chemistry; Wiley Interscience: New York, 1970; Vol. 1, pp 72-80.
15. Pei, X. F.; Lin, C. M.; Hamel, E.; Brossi, A. N-acetoacetamides of the thiocolchicine series: Synthesis and inhibition of tubulin polymerization. Med. Chem. Res. 1994, 4, 563-568.
16. Schindler, R. Structure-activity relationships in a series of colchicine analogs. J. Pharmacol. Exp. Ther. 1965, 149, 409-416.
17. Al-Tel, T. H.; Abu-Zarga, M. H.; Sabri, S. S.; Frayer, A. J.; Shamma, M. New natural colchicinoids: Indications of two possible catabolic routes for the colchicine alkaloids. J. Nat. Prod. 1990, 53, 623-629.
18. Rosner, M.; Capraro, H. G.; Jacobson, A. E.; Atwell, L.; Brossi, A.; Iorio, M. A.; Williams, T. H.; Sik, R, H.; Chignell, C. F. Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicines. J. Med. Chem. 1981, 24, 257-621.
19. Kerekes, P.; Sharma, P. N.; Brossi, A.; Chignell, C. F.; Quinn, F. R. Synthesis and biological effects of novel thiocolchicines. 3. Evaluation of N-acyldeacetylthiocolchicines, N-(alkoxycarbonyl) deacetylthiocolchicines, and O-ethyldemethylthiocolchicines. New synthesis of thiodemecolcine and antileukemic effects of 2-demethyl-and 3-demethylthiocolchicine. J. Med. Chem. 1985, 28, 1204-1208.
20. Velluz, L.; Muller, G. No. 35. La thiocolchicine. Bull. Soc. Chim. Fr. 1955, 194-197.
21. Buckley, T. F.; Rapoport, H. Mild and simple biomimetic conversion of amines to carbonyl compounds. J. Am. Chem. Soc. 1982, 104, 4446-4450.
22. Banwell, M. G.; Petters, S. C.; Greenwood, R. J.; Mackay, M. F.; Hamel, E.; Lin, C. M. Semisynthesis, X-ray crystal structures and tubulin binding-properties of 7-oxodeacetamidocolchicine and 7-oxodeacitamidoisocolchicine. Aust. J. Chem. 1992, 45, 1577-1588.
23. Kouroupis, P.; Hansen, H. J. From colchicine and some of its derivatives to 1,2,3,9,10-pentamethoxybenzo[α]heptalenes. Helv. Chim. Acta 1995, 78, 1247-1277.
24. Corey, E. J.; Bakshi, R. K.; Shibata, S. Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications. J. Am. Chem. Soc. 1987, 109, 5551-5553.
25. Hamilton, W. C. Significance tests on the crystallographic R factor. Acta Crystallogr. 1965, 18, 502-510.
26. Hamilton, W. C., Ibers. J. A., Eds. International Tables for X-Ray Crystallography; The Kynoch Press: Birmingham, England, 1974, Vol. IV.
27. Blokhin, A. V.; Yoo, H. D.; Geralds, R. S.; Nahle, D. G.; Gerwick, W. H.; Hamel, E. Characterization of the interaction of the marine cyanobacterial natural product curacin A with the colchicine site of tubulin and initial structure-activity studies with analogues. Mol. Pharmacol. 1995, 48, 523-531.