Synthesis and biological evaluation of α-methylidene-δ-lactones with 3,4-dihydrocoumarin skeleton

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 16, 2012, Pages 5017-5026

  Modranka, Jakub ^a   Albrecht, Anna ^a   Jakubowski, Rafał ^a   Krawczyk, Henryk ^a   Rózalski, Marek ^b   Krajewska, Urszula ^b   Janecka, Anna ^b   Wyrebska, Anna ^b   Rózalska, Barbara ^c   Janecki, Tomasz ^a  

^a LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^b MEDICAL UNIVERSITY OF LODZ   (Poland)

^c UNIVERSITY OF LODZ   (Poland)

Author keywords

Methylidene lactones; Antimicrobial activity; Cytotoxicity; Structure activity relationship

Indexed keywords

1 BUTYL 2 METHYLENE 1H BENZO[F]CHROMEN 3(2H) ONE; 1 BUTYL 9 HYDROXY 2 METHYLENE 1H BENZO[F]CHROMEN 3(2H) ONE; 1 ISOPROPYL 2 METHYLENE 1H BENZO[F]CHROMEN 3(2H) ONE; 1 METHYL 2 METHYLENE 1H BENZO[F]CHROMEN 3(2H) ONE; 2 METHYLENE 1 VINYL 1H BENZO[F]CHROMEN 3(2H) ONE; 4 BUTYL 5,7 DIMETHOXY 3 METHYLENECHROMAN 2 ONE; 4 BUTYL 7 METHOXY 3 METHYLENECHROMAN 2 ONE; 4 ISOPROPYL 5,7 DIMETHOXY 3 METHYLENECHROMAN 2 ONE; 4 ISOPROPYL 7 METHOXY 3 METHYLENECHROMAN 2 ONE; 5,7 DIMETHOXY 3 METHYLENE 4 VINYLCHROMAN 2 ONE; 5,7 DIMETHOXY 4 METHYL 3 METHYLENECHROMAN 2 ONE; 7 METHOXY 3 METHYLENE 4 VINYLCHROMAN 2 ONE; 7 METHOXY 4 METHYL 3 METHYLENECHROMAN 2 ONE; 7 METHYLENE 8 VINYL 7,8 DIHYDRO 6H [1,3]DIOXOLO[4,5 G]CHROMEN 6 ONE; 8 BUTYL 7 METHYLENE 7,8 DIHYDRO 6H [1,3]DIOXOLO[4,5 G]CHROMEN 6 ONE; 8 ISOPROPYL 7 METHYLENE 7,8 DIHYDRO 6H [1,3]DIOXOLO[4,5 G]CHROMEN 6 ONE; 8 METHYL 7 METHYLENE 7,8 DIHYDRO 6H [1,3]DIOXOLO[4,5 G]CHROMEN 6 ONE; 9 HYDROXY 1 ISOPROPYL 2 METHYLENE 1H BENZO[F]CHROMEN 3(2H) ONE; 9 HYDROXY 1 METHYL 2 METHYLENE 1H BENZO[F]CHROMEN 3(2H) ONE; 9 HYDROXY 2 METHYLENE 1 VINYL 1H BENZO[F]CHROMEN 3(2H) ONE; ALPHA METHYLIDINE DELTA LACTONE DERIVATIVE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; COUMARIN DERIVATIVE; DIHYDROCOUMARIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BREAST CANCER; CANDIDA ALBICANS; CELL STRAIN HL 60; CELL STRAIN HT29; CELL STRAIN MCF 7; CELL STRAIN NALM 6; COLON ADENOCARCINOMA; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PSEUDOMONAS AERUGINOSA; STRUCTURE ACTIVITY RELATION; UMBILICAL VEIN ENDOTHELIAL CELL;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; BACTERIA; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMONES; COUMARINS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

STAPHYLOCOCCUS;

EID: 84864470495     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.06.022     Document Type: Article

References (32)

1. R.R.A. Kitson, A. Millemaggi, and R.J.K. Taylor Angew. Chem., Int. Ed. 48 2009 9426
2. S. Zhang, Y.-K. Won, Ch.-N. Ong, and H.-M. Shen Curr. Med. Chem. Anticancer Agents 5 2005 239
3. J. Heilmann, M.R. Wasescha, and T.J. Smidt Bioorg. Med. Chem. 9 2001 2189
4. D.W. Knight Nat. Prod. Rep. 12 1995 271
5. S. Zhang, C.N. Ong, and H.M. Shen Cancer Lett. 208 2004 143
6. A. Albrecht, Ł. Albrecht, and T. Janecki Eur. J. Org. Chem. 2011 2747
7. S.M. Kupchan, R.J. Hemingway, D. Werner, A. Karim, A.T. McPhail, and G.A. Sim J. Am. Chem. Soc. 90 1968 3596
8. A. Nangia, G. Prasuna, and P.B. Rao Tetrahedron 53 1997 14507
9. A.J. Weinheimer, C.W.J. Chang, and J.A. Matson Fortschr. Chem. Org. Naturst. 36 1979 285
10. J.E. McMurry, and R.G. Dushin J. Am. Chem. Soc. 112 1990 6942
11. D.E. Cane, and T. Rossi Tetrahedron Lett. 20 1979 2973
12. S. Ekthawatchai, S. Kamchonwongpaisan, P. Konsgsaeree, B. Tarnchompoo, Y. Thebtaranonth, and Y. Yuthavong J. Med. Chem. 44 2001 4688
13. V. Kumar, A. Mahajan, and K. Chibale Bioorg. Med. Chem. 17 2009 2236
14. S.S. Dehal, B.A. Marples, R.J. Stretton, and J.R. Traynor J. Med. Chem. 23 1980 90
15. L.S. Chagonda, P.M. Lockey, B.A. Marples, and J.R. Traynor Steroids 43 1984 283
16. Ł. Albrecht, J. Wojciechowski, A. Albrecht, W.M. Wolf, A. Janecka, K. Studzian, U. Krajewska, M. Różalski, T. Janecki, and H. Krawczyk Eur. J. Med. Chem. 45 2010 710
17. F. Borges, F. Roleira, N. Milhazes, L. Santana, and E. Uriarte Curr. Med Chem. 12 2005 887
18. I. Kostova Curr. Med. Chem. Anticancer Agents 5 2005 29
19. F. Borges, F. Roleira, N. Milhazes, E. Uriarte, and L. Santana Front. Med. Chem. 4 2009 23
20. M.E. Riveiro, N. De Kimpe, A. Moglioni, R. Vazquez, F. Monczor, C. Shayo, and C. Davio Curr. Med. Chem. 17 2010 1325
21. X. Xu, X. Li, X. Yan, H. Wang, Y. Deng, and J. Shao Synlett 2011 3026
22. H. Krawczyk, Ł. Albrecht, J. Wojciechowski, and W.M. Wolf Tetrahedron 63 2007 12583
23. T. Janecki, and T. Wasek Tetrahedron 60 2004 1049
24. A.D. Harmon, and C.R. Hutchinson J. Org. Chem 40 1975 3474
25. J. Modranka, A. Albrecht, and T. Janecki Synlett 2010 2867
26. T. Janecki, A. Albrecht, J.K. Koszuk, J. Modranka, and D. Słowak Tetrahedron Lett. 51 2010 2274
27. E. Wong, and C.M. Giandomenico Chem. Rev. 99 1999 2451
28. R.J.L. Willems, W.P. Hanage, D.E. Bessen, and E.J. Feil FEMS Microbiol. Rev. 35 2011 872
29. S. Gibbons Planta Med. 74 2008 594
30. A. Dürig, I. Kouskoumvekaki, R.M. Vejborg, and P. Klemm Appl. Microbiol. Biotechnol. 87 2010 309
31. M. Cruz-Monteagudo, F. Borges, and M.N.D.S. Cordeiro J. Chem. Inf. Model. 51 2011 3060
32. Clinical and Laboratory Standards Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, 8th ed.; Approved standard M07-A8, 29, Clinical and Laboratory Standards Institute: Wayne, PA, 2009.