Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 27, Issue 23, 2017, Pages 5225-5229

  Xiang, Yang ^a   Chang, Ya Nan ^a   Ge, Ying ^a   Kang, Joon S ^b   Zhang, Yi Lin ^a   Liu, Xiao Long ^a   Oelschlaeger, Peter ^c   Yang, Ke Wu ^a  

^a NORTHWEST UNIVERSITY   (China)

^b CALIFORNIA STATE POLYTECHNIC UNIVERSITY   (United States)

^c WESTERN UNIVERSITY OF HEALTH SCIENCES   (United States)

Author keywords

Antibiotic resistance; Azolylthioacetamides; Inhibitor; Metallo lactamase

Indexed keywords

AZOLYLTHIOACETAMIDE; IMIPENEM; METALLO BETA LACTAMASE; THIOACETAMIDE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; BETA LACTAMASE; BETA LACTAMASE INHIBITOR; PYRROLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG POTENCY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME CONFORMATION; ESCHERICHIA COLI; HYDROGEN BOND; IC50; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; NONHUMAN; NUCLEOPHILICITY; STATIC ELECTRICITY; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; DOSE RESPONSE; DRUG EFFECTS; ENZYMOLOGY; METABOLISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; AZOLES; BETA-LACTAMASE INHIBITORS; BETA-LACTAMASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ESCHERICHIA COLI; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIOACETAMIDE;

EID: 85033214693     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2017.10.038     Document Type: Article

References (31)

1. Fleming, A., Infect Dis, 2, 1980, 129.
2. Abraham, E.P., Chain, E., Fletcher, C.M., et al. Eur J Clin Pharmacol, 42, 1992, 3.
3. Fisher, J.F., Meroueh, S., Mobashery, O.S., Chem Rev, 105, 2005, 395.
4. King, D.T.S., Sobhanifar, N.C., Strynadka, N.C.J., Protein Sci, 25, 2016, 787.
5. Ambler, R.P., Trans, P. R. Soc Lond, B Biol Sci, 289, 1980, 321.
6. Crowder, M.W., Spencer, J., Vila, A.J., Acc Chem Res, 39, 2006, 721.
7. Bebrone, C., Biochem Pharmacol, 74, 2007, 1686.
8. Yong, D.M., Toleman, A., Giske, C.G., et al. Antimicrob Agents Chemother, 53, 2009, 5046.
9. Walsh, T.R., Int J Antimicrob Agents, 36(Suppl 3), 2010, S8.
10. Mojica, M.F., Bonomo, R.A., Fast, W., Curr Drug Targets, 17, 2016, 1029.
11. Schneider, K.D., Karpen, M.E., Bonomo, R.A., Leonard, D.A., Powers, R.A., Biochemistry, 48, 2009, 11840.
12. Papp-Wallace, K.M., Endimiani, A., Taracila, M.A., Bonomo, R.A., Antimicrob Agents Chemother, 55, 2011, 4943.
13. Cornaglia, G., Giamarellou, H., Rossolini, G.M., Lancet Infect Dis, 11, 2011, 381.
14. King, A.M., Reid-Yu, S.A., Wang, W.L., et al. Nature, 510, 2014, 503.
15. Toney, J.H., Fitzgerald, P.M., Grover-Sharma, N., et al. Chem Biol, 5, 1998, 185.
16. Toney, J.H., Hammond, G.G., Fitzgerald, P.M., et al. J Biol Chem, 276, 2001, 31913.
17. Arjomandi, O.K., Husseina, W.M., Vella, P., et al. Eur J Med Chem, 114, 2016, 318.
18. Chiou, J.C., Wan, S.B., Chan, K.F., et al. Chem Commun, 51, 2015, 9543.
19. Lienard, B.M., Horsfall, L.E., Galleni, M., Frere, J.M., Schofield, C.J., Bioorg Med Chem Lett, 17, 2007, 964.
20. Brem, J.S., van Berkel, S.S., Aik, V., et al. Nat Chem, 6, 2014, 1085.
21. Zhang, Y.L., Yang, K.W., Zhou, Y.J., LaCuran, A.E., Oelschlaeger, P., Crowder, M.W., Chem Med Chem, 9, 2014, 2445.
22. Yang, S.K., Kang, J.S., Oelschlaeger, P., Yang, K.W., ACS Med Chem Lett, 6, 2015, 455.
23. Zhai, L., Zhang, Y.L., Kang, J.S., et al. ACS Med Chem Lett, 7, 2016, 413.
24. Mobinikhaledi, A., Kalhor Hatami, M., Synthesis of some new benzimidazolyl thioxoacetamide derivatives. Asian J Chem, 16, 2010.
25. Yang, H., Aitha, M., Hetrick, A.M., Richmond, T.K., Tierney, D.L., Crowder, M.W., Biochemistry, 51, 2012, 3839.
26. Wang, Z., Benkovic, S.J., J Biol Chem 273 (1998), 22402–22408.
27. Crawford, P.A., Sharma, N., Chandrasekar, S., et al. Protein Expr Purif 36 (2004), 272–279.
28. Crowder, M.W., Walsh, T.R., Banovic, L., Pettit, M., Spencer, J., Antimicrob Agents Chemother, 42, 1998, 921.
29. LaCuran, A.E., Pegg, K.M., Liu, E.M., et al. Antimicrob Agents Chemother, 59, 2015, 7299.
30. Wang, S.H., Wang, S.F., Xuan, W., et al. Bioorg Med Chem, 16, 2008, 3596.
31. Humphrey, W., Dalke, A., Schulten, K., J Mol Graphics, 14, 2009, 33.