One-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity

Archiv der Pharmazie

Volumn 346, Issue 4, 2013, Pages 266-277

  Wellington, Kevin W ^a   Qwebani Ogunleye, Tozama ^a   Kolesnikova, Natasha I ^a   Brady, Dean ^a   De Koning, Charles B ^b  

^a DSI CSIR Nanotechnology Innovation Centre   (South Africa)

^b UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

1,3 Dicarbonyls; Anticancer; Benzo b furans; Biocatalysis; C C coupling; Catechols; Cytostatic effects; Cytotoxic effects; GI50; Laccase; LC50; Michael addition; TGI

Indexed keywords

1 (5,6 DIHYDROXY 2 METHYL 1 BENZOFURAN 3 YL)ETHANONE; 1 (5,6 DIHYDROXY 2,7 DIMETHYL 1 BENZOFURAN 3 YL) ETHANONE; 7,8 DIHYDROXY 3 METHYL 3,4 DIHYDRODIBENZO[B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 3 PHENYL 3,4 DIHYDRODIBENZO[B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 3,3 DIMETHYL 3,4 DIHYDRODIBENZO[B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 3,3,6 TRIMETHYL 3,4 DIHYDRODIBENZO [B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 3,4 DIHYDRODIBENZO[B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 3,6 DIMETHYL 3,4 DIHYDRODIBENZO[B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 6 METHOXY 3 METHYL 3,4 DIHYDRODIBENZO [B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 6 METHOXY 3 PHENYL 3,4 DIHYDRODIBENZO [B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 6 METHOXY 3,4 DIHYDRODIBENZO[B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 6 METHYL 3 PHENYL 3,4 DIHYDRODIBENZO [B,D]FURAN 1(2H) ONE; 7,8 DIHYDROXY 6 METHYL 3,4 DIHYDRODIBENZO[B,D]FURAN 1(2H) ONE; ANTINEOPLASTIC AGENT; CATECHOL DERIVATIVE; ETOPOSIDE; LACCASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL; CANCER INHIBITION; CYTOSTASIS; DRUG STRUCTURE; ENZYME SYNTHESIS; HUMAN; HUMAN CELL; KIDNEY CELL; LC 50; MELANOMA CELL; ONE POT SYNTHESIS; PRIORITY JOURNAL; UTERINE CERVIX CANCER;

ANTINEOPLASTIC AGENTS; BENZOFURANS; CATECHOLS; CELL LINE, TUMOR; ETOPOSIDE; HELA CELLS; HUMANS; LACCASE; LETHAL DOSE 50; MCF-7 CELLS; NEOPLASMS;

EID: 84876106335     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.201200413     Document Type: Article

References (51)

1. M. Dean, A. Rzhetsky, R. Allikmets, Genome Res. 2001, 11, 1156-1166.
2. J. P. Gillet, T. Efferth, J. Remacle, Biochim. Biophys. Acta 2007, 1775, 237-262.
3. P. Cagniant, D. Carniant, Adv. Hetercycl. Chem. 1975, 18, 337-360.
4. D. M. X. Donnelly, M. J. Meegan, in Comprehensive Heterocyclic Chemistry, Vol. 4 (Ed.:, A. R. Katritzky,), Pergamon Press, New York 1984, Part 3, pp. 657-712.
5. M. Takasugi, S. Nagao, T. Masamune, A. Shirats, K. Takahashi, Tetrahedron Lett. 1978, 9, 797-798.
6. R. S. Ward, Nat. Prod. Rep. 1999, 16, 75-96.
7. M. S. Malamas, J. Sredy, C. Moxham, A. Katz, W. Xu, R. McDevitt, F. O. Adebayo, D. R. Sawicki, L. Seestaller, D. Sullivan, J. R. Taylor, J. Med. Chem. 2000, 43, 1293-1310.
8. C. C. Teo, O. L. Kon, K. Y. Sim, S. C. Ng, J. Med. Chem. 1992, 35, 1330-1339.
9. S. Maeda, H. Masuda, T. Tokoroyama, Chem. Pharm. Bull. 1994, 42, 2536-2545.
10. G. D. McAllister, R. C. Hartley, M. J. Dawson, A. R. Knaggs, J. Chem. Soc. Perkin Trans. 1998, 1, 3453-3458.
11. J. M. Alcides, M. P. A. da Silva, N. M. V. Silva, F. V. Brito, C. D. Buarque, D. V. de Souza, V. P. Rodrigues, E. S. C. Pocas, F. Noël, E. X. Albuquerque, P. R. R. Costa, Bioorg. Med. Chem. Lett. 2001, 11, 283-286.
12. G. D. McCallion, Curr. Org. Chem. 1999, 3, 67-76.
13. R. A. Smith, J. Chem, M. M. Mader, I. Muegge, U. Moehler, S. Katti, D. Marrero, W. G. Stirtan, D. R. Weaver, H. Xiao, W. Carley, Bioorg. Med. Chem. Lett. 2002, 12, 2875-2878.
14. M. Mayer, M. A. O'Neill, K. E. Murray, N. S. Santos-Magalhães, A. M. Carneiro-Leão, A. M. Thompson, V. C. Appleyard, Anticancer Drugs 2005, 16, 805-809.
15. I. Hayakawa, R. Shioya, T. Agatsuma, H. Furukawa, S. Naruto, Y. Sugano, Bioorg. Med. Chem. Lett. 2004, 14, 455-458
16. I. Hayakawa, R. Shioya, T. Agatsuma, Y. Sugano, Chem. Pharm. Bull. 2005, 53, 638-640
17. I. Hayakawa, R. Shioya, T. Agatsuma, H. Furukawa, S. Naruto, Y. Sugano, Bioorg. Med. Chem. Lett. 2004, 14, 4383-4387.
18. A. Yaropolov, O. Skorobogatko, S. Vartanov, S. Varfolomeyev, Appl. Biochem. Biotechnol. 1994, 49, 257-280.
19. C. F. Thurston, Microbiology 1994, 140, 19-26.
20. S. Burton, Curr. Org. Chem. 2003, 7, 1317-1331.
21. T. H. Niedermeyer, A. Mikolasch, M. Lalk, J. Org. Chem. 2005, 70, 2002-2008
22. S. Riva, Trends Biotechnol. 2006, 24, 219-226
23. S. Ciecholewski, E. Hammer, K. Manda, G. Bose, V. T. H. Nguyen, P. Langer, F. Schauer, Tetrahedron 2005, 61, 4615-4619
24. M. Kurisawa, J. E. Chung, H. Uyama, S. Kobayashi, Biomacromolecules 2003, 4, 1394-1399
25. A. Mikolasch, E. Hammer, U. Jonas, K. Popowski, A. Stielow, F. Schauer, Tetrahedron 2002, 58, 7589-7593
26. M. Hosny, J. Rosazza, J. Agric. Food Chem. 2002, 50, 5539-5545
27. A. Schäfer, M. Specht, A. Hetzheim, W. Francke, F. Schauer, Tetrahedron 2001, 57, 7693-7699
28. K. Manda, E. Hammer, A. Mikolasch, T. Niedermeyer, J. Dec, A. D. Jones, A. J. Benesi, F. Schauer, J.-M. Bollag, J. Mol. Catal. B: Enzym. 2005, 35, 86-92
29. H. Leutbecher, J. Conrad, I. Klaiber, U. Beifuss, Synlett 2005, 20, 3126-3130
30. S. Witayakran, A. J. Ragauskas, Adv. Synth. Catal. 2009, 351, 1187-1209
31. A. Kunamneni, S. Camarero, C. García-Burgos, F. J. Plou, A. Ballesteros, M. Alcalde, Microb. Cell Factory 2008, 7, 32
32. F. Xu, T. Damhus, S. Danielsen, L. H. Østergaard, in Modern Biooxidations, Enzymes, Reactions and Applications (Eds.:, R. D. Schmid, V. Urlacher,), Wiley-VCH, Weinheim 2007, p. 43.
33. K. W. Wellington, P. Steenkamp, D. Brady, Bioorg. Med. Chem. 2010, 18, 1406-1414
34. K. W. Wellington, N. I. Kolesnikova, Bioorg. Med. Chem. 2012, 20, 4472-4481
35. K. W. Wellington, R. Bokako, N. Raseroka, P. Steenkamp, Green Chem. 2012, 14, 2567-2576.
36. R. W. Middleton, J. Parrick, in The Chemistry of Quinonoid Compounds (Eds.:, S. Patak, Z. Rappoport,), John Wiley & Sons, London 1988, pp. 1019-1066.
37. A. N. Semenov, I. V. Lomonsova, V. I. Berezin, M. I. Titov, Biotechnol. Bioeng. 1993, 42, 1137-1141
38. J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, H. E. Schoemaker, M. Schürmann, F. L. van Delft, F. P. J. T. Rutjes, Adv. Synth. Catal. 2007, 349, 1332-1336.
39. S. Witayakran, L. Gelbaum, A. J. Ragauskas, Tetrahedron 2007, 63, 10958-10962.
40. S. Witayakran, A. Ragauskas, J. Eur. J. Org. Chem. 2009, 3, 358-363.
41. S. Hajdok, H. Leutbecher, G. Greiner, J. Conrad, U. Beifuss, Tetrahedron Lett. 2007, 48, 5073-5076.
42. H. Leutbecher, S. Hajdok, C. Braunberger, M. Neumann, S. Mika, J. Conrad, U. Beifuss, Green Chem. 2009, 11, 676-679.
43. L.-X. Pei, Y.-M. Li, X.-Z. Bu, L.-Q. Gu, A. S. C. Chan, Tetrahedron Lett. 2006, 47, 2615-2618.
44. R. O. Duthaler, V. Scherrer, Helv. Chim. Acta 1984, 67, 1767-1775.
45. Z. Grujic̈, I. Tabakovic̈, M. Trkovnik, Tetrahedron Lett. 1976, 17, 4823-4824.
46. I. Tabakovic̈, Z. Grujic̈, Z. Bejtovic̈, J. Heterocycl. Chem. 1983, 20, 635-638.
47. D. Nematollahi, D. Habibi, M. Rahmati, M. Rafiee, J. Org. Chem. 2004, 69, 2637-2640.
48. S. S. H. Davarani, N. M. Najafi, S. Ramyar, L. Masoumi, M. Shamsipur, Chem. Pharm. Bull. 2006, 54, 959-962.
49. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J. T. Warren, H. Bokesch, S. Kenney, M. R. Boyd, J. Natl. Cancer Inst. 1990, 82, 1107-1112.
50. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, J. Natl. Cancer Inst. 1991, 83, 757-766.
51. C.-C. Wu, T.-K. Li, L. Farh, L.-Y. Lin, T.-S. Lin, Y.-J. Yu, T.-J. Yen, C.-W. Chiang, N.-L. Chan, Science 2011, 333, 459-462.