Synthesis and biological evaluation of new pleuromutilin derivatives as antibacterial agents

Molecules

Volumn 19, Issue 11, 2014, Pages 19050-19065

  Shang, Ruo Feng ^a   Wang, Guan Hua ^b   Xu, Xi Ming ^c   Liu, Si Jie ^d   Zhang, Chao ^a   Yi, Yun Peng ^a   Liang, Jian Ping ^a   Liu, Yu ^a  

^a INSTITUTE OF PLANT PROTECTION   (China)

^b LANZHOU UNIVERSITY   (China)

^c GUIZHOU MEDICAL UNIVERSITY   (China)

^d SHIJIAZHUANG UNIVERSITY   (China)

Author keywords

ADMET properties; Antibacterial activity; Molecular docking; Pleuromutilin derivatives; Synthesis

Indexed keywords

ANTIINFECTIVE AGENT; DITERPENE; PLEUROMUTILIN;

BACTERIUM; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; MOLECULAR DOCKING; PROCEDURES; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BACTERIA; DITERPENES; MICROBIAL SENSITIVITY TESTS; MOLECULAR DOCKING SIMULATION;

EID: 84912095857     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules191119050     Document Type: Article

References (25)

1. Kavanagh, F.; Hervey, A.; Robbins, W.J. Antibiotic Substances From Basidiomycetes: VIII. Pleurotus Multilus (Fr.) Sacc. and Pleurotus Passeckerianus Pilat. Proc. Natl. Acad. Sci. USA 1951, 37, 570-574
2. Arigoni, D. Structure of a new type of terpene. Gazz. Chem. Ital. 1962, 92, 884-901
3. Birch, A.J.; Holzapfel, C.W.; Richards, R.W. Diterpenoid nature of pleuromutilin. Chem. Ind. 1963, 14, 374-375
4. Shang, R.F.; Liu, Y.; Xin, Z.J.; Guo, W.Z.; Guo, Z.T.; Hao, B.C.; Liang, J.P. Synthesis and antibacterial evaluation of novel pleuromutilin derivatives. Eur. J. Med. Chem. 2013, 63, 231-238
5. Tang, Y.Z.; Liu, Y.H.; Chen, J.X. Pleuromutilin and its derivatives-The lead compounds for novel antibiotics. Mini Rev. Med. Chem. 2012, 12, 53-61
6. Moody, M.N.; Morrison, L.K.; Tyring S.K. Retapamulin: What is the role of this topical antimicrobial in the treatment of bacterial infections in atopic dermatitis? Skin Ther. Lett. 2010, 15, 1-4
7. Sader, H.S.; Paukner, S.; Ivezic-Schoenfeld, Z.; Biedenbach, D.J.; Schmitz, F.J.; Jones, R.N. Antimicrobial activity of the novel pleuromutilin antibiotic BC-3781 against organisms responsible for community-acquired respiratory tract infections (CARTIs). J. Antimicrob. Chemother. 2012, 67, 1170-1175
8. Shang, R.F.; Wang, J.T.; Guo, W.Z.; Liang, J.P. Efficient antibacterial agents: A review of the synthesis, biological evaluation and mechanism of pleuromutilin derivatives. Curr. Top. Med. Chem. 2013, 13, 3013-3025
9. Novak, R.; Shlaes, D.M. The pleuromutilin antibiotics: A new class for human use. Curr. Opin. Invest. Drugs 2010, 11, 182-191
10. Schlunzen, F.; Pyetan, E.; Fucini, P.; Yonath, A.; Harms, J.M. Inhibition of peptide bond formation by pleuromutilins: The structure of the 50S ribosomal subunit from Deinococcus radiodurans in complex with tiamulin. Mol. Microbiol. 2004, 54, 1287-1294
11. Davidovich, C.; Bashan, A.; Auerbach-Nevo, T.; Yaggie, R.D.; Gontarek, R.R.; Yonath, A. Induced-fit tightens pleuromutilins, binding to ribosomes and remote interactions enable their selectivity. Proc. Natl. Acad. Sci. USA 2007, 104, 4291-4296
12. Long, K.S.; Hansen, L.H.; Jakobsen, L.; Vester, B. Interaction of pleuromutilin derivatives with the ribosomal peptidyl transferase center. Antimicrob. Agent. Chemother. 2006, 50, 1458-1462
13. Popiolek, L.; Kosikowska, U.; Mazur, L.; Dobosz, M.; Malm, A. Synthesis and antimicrobial evaluation of some novel 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Med. Chem. Res. 2013, 22, 3134-3147
14. Aliabadi, A.; Eghbalian, E.; Kiani, A. Synthesis and evaluation of the cytotoxicity of a series of 1,3,4-thiadiazole based compounds as anticancer agents. Iran J. Basic Med. Sci. 2013, 16, 1133-1138
15. Chandrakantha, B.; Isloor, A.M.; Shetty, P.; Fun, H.K.; Hegde, G. Synthesis and biological evaluation of novel substituted 1,3,4-thiadiazole and 2,6-di aryl substituted imidazo [2,1-b] [1,3,4] thiadiazole derivatives. Eur. J. Med. Chem. 2014, 71, 316-323
16. Shang, R.F.; Pu, X.Y.; Xu, X.M.; Xin, Z.J.; Zhang, C.; Guo, W.Z.; Liu, Y.; Liang, J.P. Synthesis and Biological Activities of Novel Pleuromutilin Derivatives with a Substituted Thiadiazole Moiety as Potent Drug-Resistant Bacteria Inhibitors. J. Med. Chem. 2014, 57, 5664-5678
17. Marialke, J.; Tietze, S.; Apostolakis, J. Similarity based docking. J. Chem. Inf. Model. 2008, 48, 186-196
18. Vyas, V.K.; Gupta, N.; Ghate M.; Patel, S. Design, synthesis, pharmacological evaluation and in silico ADMET prediction of novel substituted benzimidazole derivatives as angiotensin II-AT1 receptor antagonists based on predictive 3D QSAR models. SAR QSAR Environ. Res. 2014, 25, 117-146
19. Lanevskij, K.; Japertasa, P.; Didziapetrisa, R.; Petrauskasa, A. Ionization-specific QSAR models of blood-brain penetration of drugs. Chem. Biodivers. 2009, 6, 2050-2054
20. Waterbeemd, H.; Gifford, E. ADMET in silico modelling: Towards prediction paradise? Nat. Rev. Drug Discov. 2003, 2, 192-204
21. Marcus, D.H.; Donald, E.C.; David, C.L.; Tim, V.; Eva, Z.; Geoffrey, R.H. Avogadro: An advanced semantic chemical editor, visualization, and analysis platform. J. Cheminform. 2012, 4, 17
22. Stierand, K.; Maaß, P.; Rarey, M. Molecular complexes at a glance: Automated generation of two-dimensional complex diagrams. Bioinformatics 2006, 22, 1710-1716
23. Delano, W.L.; Ultsch, M.H.; De Vos, A.M.; Wells, J.A. Convergent solutions to binding at a protein-protein interface. Science 2000, 287, 1279-1283
24. Hou, T.J.; Xu, X.J. ADME evaluation in drug discovery Modeling blood-brain barrier partitioning using simple molecular descriptors. J. Chem. Inf. Comput. Sci. 2003, 43, 2137-2152
25. Stankovic, N.; Mladenovic, M.; Mihailovic, M.; Arambasic, J.; Uskokovic, A.; Stankovic, V.; Mihailovic, V.; Katanic, J.; Matic, S.; Solujic, S.; et al. Synthesis and toxicological studies of in vivo anticoagulant activity of novel 3-(1-aminoethylidene)chroman-2,4-diones and 4-hydroxy-3-(1-iminoethyl)-2H-chromen-2-ones combined with a structure-based 3-D pharmacophore model. Eur. J. Pharm. Sci. 2014, 55, 20-35