Design, synthesis and biological evaluation of potential antibacterial butyrolactones

Bioorganic and Medicinal Chemistry

Volumn 24, Issue 22, 2016, Pages 5823-5833

  Sweidan, Alaa ^a,c   Chollet Krugler, Marylene ^b   van de Weghe, Pierre ^b   Chokr, Ali ^c   Tomasi, Sophie ^b   Bonnaure Mallet, Martine ^a   Bousarghin, Latifa ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

^c LEBANESE UNIVERSITY   (Lebanon)

Author keywords

Antibacterial; Butyrolactones; Cytotoxicity; Lichen; Streptococcus gordonii

Indexed keywords

2 HEPTYL 4 METHYL 5 OXO 2,5 DIHYDROFURAN 3 CARBOXYLIC ACID; 2 HEXADECYL 4 METHYL 5 OXO 2,5 DIHYDROFURAN 3 CARBOXYLIC ACID; 4 METHYL 2 NONYL 5 OXO 2,5 DIHYDROFURAN 3 CARBOXYLIC ACID; 4 METHYL 5 OXO 2 PENTADECYL 2,5 DIHYDROFURAN 3 CARBOXYLIC ACID; ANTIINFECTIVE AGENT; BUTYROLACTONE; BUTYROLACTONE DERIVATIVE; DOXYCYCLINE; LACTATE DEHYDROGENASE; LICHESTERINIC ACID; UNCLASSIFIED DRUG; LACTONE;

ARTICLE; BACTERICIDAL ACTIVITY; BROTH DILUTION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPITHELIUM CELL; GINGIVA; HUMAN; HUMAN CELL; IN VITRO STUDY; MACROPHAGE; MINIMUM INHIBITORY CONCENTRATION; MTT ASSAY; NONHUMAN; STREPTOCOCCUS GORDONII; STRUCTURE ACTIVITY RELATION; CELL LINE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CELL LINE; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HUMANS; LACTONES; MACROPHAGES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STREPTOCOCCUS GORDONII; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84992192166     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2016.09.040     Document Type: Article

References (32)

1. 1 Andersson, D.I., Hughes, D., Drug Resist. Update, 15, 2012, 162.
2. 2 Khan, A.V., Ahmed, Q.U., Shukla, I., Khan, A.A., Asian Pac. J. Trop. Biomed., 2, 2012, 189.
3. 3 Simões, M., Bennett, R.N., Rosa, E.A.S., Nat. Prod. Rep., 26, 2009, 746.
4. 4 Nabavi, S., Di Lorenzo, A., Izadi, M., Sobarzo-Sánchez, E., Daglia, M., Nabavi, S., Nutrients, 7, 2015, 7729.
5. 5 Shrestha, G., Raphael, J., Leavitt, S.D., St. Clair, L.L., Pharm. Biol., 52, 2014, 1262.
6. 6 Shrestha, G., Clair, L.L.St., Phytochem. Rev., 12, 2013, 229.
7. 7 Boustie, J., Grube, M., Plant Genet. Resour. Charact. Util., 3, 2005, 273.
8. 8 Shukla, V., Joshi, G.P., Rawat, M.S.M., Phytochem. Rev., 9, 2010, 303.
9. 9 Bačkorová, M., Jendželovský, R., Kello, M., Bačkor, M., Mikeš, J., Fedoročko, P., Toxicol. Vitro Int. J. Publ. Assoc. Bibra, 26, 2012, 462.
10. 10 Yombi, J.cyr, Belkhir, L., Jonckheere, S., Wilmes, D., Cornu, O., Vandercam, B., Rodriguez-Villalobos, H., BMC Infect. Dis., 12, 2012, 215.
11. 11 Wood, N.J., Jenkinson, H.F., Davis, S.A., Mann, S., O'Sullivan, D.J., Barbour, M.E., J. Mater. Sci. Mater. Med., 26, 2015, 201.
12. 12 Huang, R., Li, M., Ye, M., Yang, K., Xu, X., Gregory, R.L., Appl. Environ. Microbiol., 80, 2014, 7212.
13. 13 Kuboniwa, M., Lamont, R.J., Periodontology 2000, 52, 2010, 38.
14. 14 Loo, C.Y., Corliss, D.A., Ganeshkumar, N., J. Bacteriol., 182, 2000, 1374.
15. 15 Rogers, J.D., Haase, E.M., Brown, A.E., Douglas, C.W., Gwynn, J.P., Scannapieco, F.A., Microbiol. Read. Engl., 144, 1998, 1223.
16. 16 Cavallito, C.J., Fruehauf, D.M., Bailey, J.H., J. Am. Chem. Soc., 70, 1948, 3724.
17. 17 Braukmüller, S., Brückner, R., Eur. J. Org. Chem., 2006, 2110.
18. 18 Perepogu, A.K., Raman, D., Murty, U.S.N., Rao, V.J., Synth. Commun., 40, 2010, 686.
19. 19 Guzman, J.D., Gupta, A., Evangelopoulos, D., Basavannacharya, C., Pabon, L.C., Plazas, E.A., Munoz, D.R., Delgado, W.A., Cuca, L.E., Ribon, W., Gibbons, S., Bhakta, S., J. Antimicrob. Chemother., 65, 2010, 2101.
20. 20 Yang, Y., Ye, X., Li, X., Zhen, J., Zhang, B., Yuan, L., Planta Med., 73, 2007, 602.
21. 21 Sebastianes, F.L.S., Cabedo, N., Aouad, N.E., Valente, A.M.M.P., Lacava, P.T., Azevedo, J.L., Pizzirani-Kleiner, A.A., Cortes, D., Curr. Microbiol., 65, 2012, 622.
22. 22 Kitani, S., Miyamoto, K.T., Takamatsu, S., Herawati, E., Iguchi, H., Nishitomi, K., Uchida, M., Nagamitsu, T., Omura, S., Ikeda, H., Nihira, T., Proc. Natl. Acad. Sci. U.S.A., 108, 2011, 16410.
23. 23 Berkenbusch, T., Brückner, R., Tetrahedron, 54, 1998, 11471.
24. 24 Fernandes, R.A., Chowdhury, A.K., Eur. J. Org. Chem., 2011, 2011, 1106.
25. 25 Kuhajda, F.P., Pizer, E.S., Li, J.N., Mani, N.S., Frehywot, G.L., Townsend, C.A., Proc. Natl. Acad. Sci. U.S.A., 97, 2000, 3450.
26. 26 Boustie, J.; Galibert-Anne, M.-D.; Lohezic-Le Devehat, F.; Chollet-Krugler, M.; Tomasi, S.; Mouchet, N.; Legouin-Gardadennec, B. US Pat. US 20,150,105,459, 2015.
27. 27 Huneck, S., Takeda, R., Z. Naturforsch., B, 1992, 47.
28. 28 Huneck, S., Schreiber, K., Höfle, G., Snatzke, G., J. Hattori Bot. Lab., 45, 1979, 1.
29. 29 Nicolle, O., Rouillon, A., Guyodo, H., Tamanai-Shacoori, Z., Chandad, F., Meuric, V., Bonnaure-Mallet, M., FEMS Immunol. Med. Microbiol., 2010.
30. 30 Donlan, R.M., Costerton, J.W., Clin. Microbiol. Rev., 15, 2002, 167.
31. 31 Hecht, D.W., National Committee for Clinical Laboratory Standards, Methods for antimicrobial Susceptibility Testing of Anaerobic Bacteria: Approved Standard. 6th ed., 2004, NCCLS, Wayne, Pa.
32. 32 Mosmann, T., J. Immunol. Methods, 65, 1983, 55.