The synthesis and antibacterial activity of pyrazole-fused tricyclic diterpene derivatives

European Journal of Medicinal Chemistry

Volumn 90, Issue , 2015, Pages 10-20

  Yu, Li Gang ^a   Ni, Teng Feng ^b   Gao, Wei ^a   He, Yuan ^a   Wang, Ying Ying ^a   Cui, Hai Wei ^a   Yang, Cai Guang ^b   Qiu, Wen Wei ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Antibacterial; Cyclization reaction; Diterpene derivative; Multidrug resistant; Synthesis

Indexed keywords

ANTIBIOTIC AGENT; PYRAZOLE DERIVATIVE; PYRAZOLE FUSED TRICYCLIC DITERPENE DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; DITERPENE; PYRAZOLE;

ADULT; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; DOSE RESPONSE; DRUG EFFECTS; FIBROBLAST; MICROBIAL SENSITIVITY TEST; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTI-BACTERIAL AGENTS; CRYSTALLOGRAPHY, X-RAY; DITERPENES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, MULTIPLE, BACTERIAL; FIBROBLASTS; HUMANS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRAZOLES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84909960152     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.11.015     Document Type: Article

References (23)

1. N. Woodford, D.M. Livermore, Infections caused by gram-positive bacteria: a review of the global challenge, J. Infect. 59 (2009) S4eS16
2. L.C. Balsalobre, M. Dropa, M.H. Matté, An overview of antimicrobial resistance and its public health significance, Braz. J. Microbiol. 45 (2014) 1e5
3. H.F. Chambers, Methicillin-resistant Staphylococcus aureus. Mechanisms of resistance and implications for treatment, Postgrad. Med. 109 (2001) 43e50
4. S.M. Drawz, R.A. Bonomo, Three decades of beta-lactamase inhibitors, Clin. Microbiol. Rev. 23 (2010) 160e201
5. E. Klein, D.L. Smith, R. Laxminarayan, Hospitalizations and deaths caused by methicillin- resistant Staphylococcus aureus, United States, 1999e2005, Emerg. Infect. Dis. 13 (2007) 1840e1846
6. G.A. Noskin, R.J. Rubin, J.J. Schentag, J. Kluytmans, E.C. Hedblom, C. Jacobson, M. Smulders, E. Gemmen, M. Bharmal, National trends in Staphylococcus aureus infection rates: impact on economic burden and mortality over a 6-year period (1998e2003), Clin. Infect. Dis. 45 (2007) 1132e1140
7. M. Upshaw-Owens, C.A. Bailey, Preventing hospital-Associated infection: MRSA, Medsurg Nurs. 21 (2012) 77e81
8. M.C. Bonito, C. Cicala, M.C. Marcotullio, F. Maione, N. Mascolo, Biological activity of bicyclic and tricyclic diterpenoids from Salvia species of immediate pharmacological and pharmaceutical interest, Nat. Prod. Commun. 6 (2011) 1205e1215
9. R.K. Devappa, H.P.S. Makkar, K. Becker, Jatropha diterpenes: a review, J. Am. Oil Chem. Soc. 88 (2011) 301e322
10. C. Valente, M. Pedro, A. Duarte, M.S. Nascimento, P.M. Abreu, M.J. Ferreira, Bioactive diterpenoids, a new jatrophane and two ent-Abietanes, and other constituents from Euphorbia pubescens, J. Nat. Prod. 67 (2004) 902e904
11. Y.I. Matsushita, Y.H. Hwang, K. Sugamoto, T. Matsui, Antimicrobial activity of heartwood components of sugi (Cryptomeria japonica) against several fungi and bacteria, J. Wood Sci. 52 (2006) 552e556
12. I. Kubo, H. Muroi, M. Himejima, Antibacterial activity of totarol and its potentiation, J. Nat. Prod. 55 (1992) 1436e1440
13. H. Muroi, I. Kubo, Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus, J. Appl. Bacteriol. 80 (1996) 387e394
14. H. Muroi, I. Kubo, Bactericidal effects of anacardic acid and totarol on methicillin eresistant Staphylococcus aureus (MRSA), Biosci. Biotechnol. Biochem. 58 (1994) 1925e1926
15. K. . lson, G. . Evans, P.W. O'Toole, Potentiation of methicillin activity against methicillin- resistant Staphylococcus aureus by diterpenes, FEMS Microbiol. Lett. 179 (1999) 233e239
16. L.L. Silver, Are natural products still the best source for antibacterial discovery? The bacterial entry factor, Expert Opin. Drug Discov. 3 (2008) 487e500
17. J.F. Zhao, Y.J. Zhao, T.P. Loh, Indium tribromide-promoted arene-Terminated epoxy olefin cyclization, Chem. Commun. (2008) 1353e1355
18. K. Surendra, E.J. Corey, A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol, J. Am. Chem. Soc. 131 (2009) 13928e13929
19. A. Eschenmoser, D. Arigoni, Revisited after 50 years: the stereochemical interpretation of the biogenetic isoprene rule for the triterpenes, Helv. Chim. Acta 88 (2005) 3011e3350
20. G. Stork, A.W. Burgstaher, The stereochemistry of polyene cyclization, J. Am. Chem. Soc. 77 (1955) 5068e5077
21. CCDC 978557 contains the supplementary crystallographic data of compound 2 for this paper. These data can be obtained free of charge viahttp://www. ccdc.cam.ac.uk/cgi-bin/catreq.cgi or by emailing data-request@ccdc.cam.ac. uk or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, U.K. (fax, 44 1223 336 33
22. G.B. Evans, R.H. Furneaux, M.B. Gravestock, G.P. Lynch, G.K. Scott, The synthesis and antibacterial activity of totarol derivatives. Part 1: modifications of ring-C and pro-drugs, Bioorg Med. Chem. 7 (1999) 1953e1964
23. M.B. Kim, T.E. O'Brien, J.T. Moore, D.E. Anderson, M.H. Foss, D.L. Weibel, J.B. Ames, J.T. Shaw, The synthesis and antimicrobial activity of heterocyclic derivatives of totarol, ACS Med. Chem. Lett. 3 (2012) 818e822