Synthesis, molecular modeling and preliminary biological evaluation of a set of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole as potential antibacterial, anti-Trypanosoma cruzi and antifungal agents

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 21, 2011, Pages 6292-6301

  Ishii, Marina ^a   Jorge, Salomão Dória ^a   De Oliveira, Alex Alfredo ^a   Palace Berl, Fanny ^a   Sonehara, Ieda Yuriko ^a   Pasqualoto, Kerly Fernanda Mesquita ^a   Tavares, Leoberto Costa ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Bacterial resistance; candida albicans; MRSA; oxadiazolines; trypanosoma cruzi; VISA

Indexed keywords

2,3 DIHYDRO 1,3,4 OXADIAZOLE DERIVATIVE; 3 ACETYL 5 (4 ACETOXYPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 BROMOPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 CHLOROPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 CYANOPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 ETHOXYPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 ETHYLPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 IODOPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 METHOXYPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 METHYLPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 N BUTOXYPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 N PROPOXYPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 N PROPYLPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 NITROPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 (4 TRIFLUOROMETHYLPHENYL) 2 (5 NITROTHIOPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; 3 ACETYL 5 PHENYL 2 (5 NITROPHEN 2 YL) 2,3 DIHYDRO 1,3,4 OXADIAZOLE; AMOXICILLIN PLUS CLAVULANIC ACID; AMPICILLIN; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ANTITRYPANOSOMAL AGENT; BENZNIDAZOLE; CEFALOTIN; CEFOTAXIME; CIPROFLOXACIN; CLINDAMYCIN; ERYTHROMYCIN; NIFUROXAZIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN; ANTIPROTOZOAL AGENT; OXADIAZOLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIPROTOZOAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR MODEL; NONHUMAN; PARASITE DEVELOPMENT; PHYSICAL CHEMISTRY; QUALITATIVE ANALYSIS; STAPHYLOCOCCUS AUREUS; TRYPANOSOMA CRUZI; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

BACTERIA (MICROORGANISMS); CANDIDA ALBICANS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS AUREUS; TRYPANOSOMA CRUZI;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; ANTIPROTOZOAL AGENTS; CANDIDA ALBICANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; OXADIAZOLES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA CRUZI;

EID: 80054921077     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.09.009     Document Type: Article

References (40)

1. Rice, L. B. Am. J. Infect. Control 2006, 34, S11.
2. Pfaller, M. A.; Pappas, P. G.; Wingard, J. R. Clin. Infect. Dis. 2006, 43, S3.
3. Urbina, J. A.; Docampo, R. Trends Parasitol. 2003, 19, 495.
4. Siles, R.; Chen, S.; Zhou, M.; Pinney, K. G.; Trawick, M. L. Bioorg. Med. Chem. Lett. 2006, 16, 4405.
5. Zhao, H.; Guo, Z. Drug Discovery Today 2009, 14, S16.
6. Masunari, A.; Tavares, L. C. Br. J. Pharm. Sci. 2006, 42, 461.
7. Behrouzi-Fardmoghadam, M.; Poorrajab, F.; Ardestani, S. K.; Emami, S.; Shafiee, A.; Foroumadi, A. Bioorg. Med. Chem. 2008, 42, 4509.
8. Rollas, S.; Gulerman, N.; Erdeniz, H. Il Farmaco 2002, 57, 171.
9. Parmar, S. S.; Gupta, A. K.; Gupta, T. K.; Stenberg, V. I. J. Pharm. Sci. 1975, 64, 154.
10. Kalsi, R.; Pande, K.; Balla, T. N.; Bartwall, J. P.; Gupta, G. P.; Parmar, S. S. J. Pharm. Sci. 1990, 79, 317.
11. Li, C.; Ma, Y.; Cao, L. J. Chin. Chem. Soc. 2009, 56, 182.
12. Masunari, A.; Sonehara, I. Y.; Pasqualoto, K. F. M.; Tavares, L. C. QSAR Comb. Sci. 2009, 28, 1546.
13. Paula, F. R.; Jorge, S. D.; Almeida, L. V.; Pasqualoto, K. F. M.; Tavares, L. C. Bioorg. Med. Chem. 2009, 17, 2673.
14. Masunari, A.; Tavares, L. C. Bioorg. Med. Chem. 2007, 15, 4229.
15. Cao, C.; Liu, L. J. Chem. Inf. Comput. Sci. 2004, 44, 678.
16. Ghose, A. K.; Viswanadhan, V. N. J.; Wendoloski, J. J. Phys. Chem. A 1998, 102, 3762.
17. Ash, S.; Cline, M. A.; Homer, R. W.; Hurst, T.; Smith, G. B. J. Chem. Inf. Comput. Sci. 1997, 37, 71.
18. Sybyl 8.0 for Linux; Tripos, Inc.: 2007. 1699 South Hanley Rd., St. Louis, MO 63144-2917, USA.
19. Marvin 5.3.8 software -Calculator Plugins, 2010, ChemAxon Ltd., Budapest, 1037, Hungary (http://www.chemaxon.com).
20. Jorge, S. D.; Masunari, A.; Rangel-Yagui, C. O.; Pasqualoto, K. F. M.; Tavares, L. C. Bioorg. Med. Chem. 2009, 17, 3028.
21. Schvartzapel, A. J.; Zhong, L.; Docampo, R.; Rodriguez, J. B.; Gros, E. G. J. Med. Chem. 1997, 40, 2314.
22. Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujváry, I.; Szajnman, S. H.; Rodriguez, J. B. J. Med. Chem. 2002, 45, 3984.
23. Cerecetto, H.; Maio, R. D.; Ibarruri, G.; Seoane, G.; Denicola, A.; Pefullo, G.; Quijano, C.; Paulino, M. Il Farmaco 1998, 53, 89.
24. Aguirre, G.; Boiani, L.; Boiani, M.; Cerecetto, H.; Di Maio, R.; González, M.; Porcal, W.; Denicola, A.; Piro, O. E.; Castellano, E. E.; Sant'anna, C. M. R.; Barreiro, E. J. Bioorg. Med. Chem. 2005, 13, 6336.
25. Arán, V. J.; Ochoa, C.; Boiani, L.; Buccino, P.; Cerecetto, H.; Gerpe, A.; González, M.; Montero, D.; Nogal, J. J.; Gomez-Barrio, A.; Azqueta, A.; Cerain, A. L.; Piro, O. E.; Castellano, E. E. Bioorg. Med. Chem. 2005, 13, 3197.
26. Cerecetto, H.; Di Maio, R.; Risso, M.; Saenz, P.; Seoane, G.; Denicola, A.; Peluffo, G.; Quijano, C.; Olea-Azar, C. J. Med. Chem. 1999, 42, 1941.
27. Aguirre, G.; Cerecetto, H.; Di Maio, R.; González, M.; Porcal, W.; Seoane, G.; Ortega, M. A.; Aldana, I.; Monge, A.; Denicola, A. Arch. Pharm. 2002, 335, 15.
28. Aguirre, G.; Boiani, L.; Cerecetto, H.; Di Maio, R.; González, M.; Porcal, W.; Denicola, A.; Moller, M.; Thomson, L.; Tortora, V. Bioorg. Med. Chem. 2005, 13, 6324.
29. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standards. Document M27A2. Wayne, PA: National Committee for Clinical Laboratory Standards, 2002.
30. Wang, X.; Wang, W.; Liu, H. X. Acta Crystallogr., Sect. C 1995, 51, 1585.
31. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
32. HyperChem Program Release 7.51 for Windows; Hypercube, Inc., Gainesville, FL 2002.
33. Dewar, M. J. S. E.; Zoebisch, G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
34. Doherty, D. MOLSIM: Molecular Mechanics and Dynamics Simulation Software, version 3.2 -User's Guide. The Chem21 Group Inc., 1780 Wilson Dr., Lake Forest, IL, 60045, EUA, 2002.
35. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361.
36. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
37. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
38. Gaussian 03, Revision B.03, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Jr., Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fqytqterukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 2003.
39. Connolly, M. L. Science 1983, 221, 709.
40. Connolly, M. L. J. Appl. Crystallogr. 1983, 16, 548.