Abstract
A series of twelve 5-trihalomethyl-3-arylisoxazoles was synthesized and screened for antibacterial and antifungal activities. The compounds were synthesized from the cyclondensation of 1,1,1-trihalo-4-alkoxy-3-alken-2-ones [CX 3C(O)C(R 2)=C(R 1)OR, where X = Cl and F; R=Me; R 2=H; R 1=H, Me, F, Cl, Br, and NO2] with hydroxylamine hydrochloride through a rapid one-pot reaction via microwave irradiation. Some of the 5-trihalomethyl-3-arylisoxazoles exhibited good in vitro anti-Cryptococcus activity.
Similar content being viewed by others
References
ED Brown GD Wright (2005) Chem Rev 105 759 Occurrence Handle10.1021/cr030116o Occurrence Handle1:CAS:528:DC%2BD2MXjtFKjtA%3D%3D
A Coates Y Hu R Bax C Page (2002) Nat Rev Drug Discov 1 895 Occurrence Handle10.1038/nrd940 Occurrence Handle1:CAS:528:DC%2BD38XotleqtLk%3D
A Espinel-Ingroff T White MA Pfaller (1999) Antifungal Agents and Susceptibility Tests PR Murray EJ Baron MA Pfaller FC Tenover (Eds) Manual of Clinical Microbiology EditionNumber7 ASM Press Washington 1640
JH Jorgensen JD Turnidge JA Washington (1999) Antibacterial Susceptibility Tests: Dilution and Disk diffusion methods PR Murray EJ Baron MA Pfaller FC Tenover RH Yolken (Eds) Manual of Clinical Microbiology EditionNumber7 ASM Press Washington 1526
JJ Talley DL Brown JS Carter MJ Graneto CM Koboldt JL Masferrer WE Perkins RS Rogers AF Shaffer YY Zhang BS Zweifel KJ Seibert (2000) J Med Chem 43 775 Occurrence Handle10.1021/jm990577v Occurrence Handle1:CAS:528:DC%2BD3cXht1aiurw%3D
Y Lee BH Kim (2002) Bioorg Med Chem Lett 12 1395 Occurrence Handle10.1016/S0960-894X(02)00182-8 Occurrence Handle1:CAS:528:DC%2BD38Xjt1CqsLk%3D
D Raffa G Daidone B Maggio S Cascioferro F Plescia D Schillaci (2004) Farmaco 59 451 Occurrence Handle10.1016/j.farmac.2003.10.006 Occurrence Handle1:CAS:528:DC%2BD2cXkslWrsbc%3D
B Frølund JR Greenwood MM Holm J Egebjerg U Madsen B Nielsen H Bräuner-Osborne TB Stensbølc P Krogsgaard-Larsen (2005) Bioorg Med Chem 13 5391 Occurrence Handle10.1016/j.bmc.2005.06.024 Occurrence Handle1:CAS:528:DC%2BD2MXnslOqu7k%3D
BH Norman PA Lander JM Gruber JS Kroin JD Cohen LN Jungheim JJ Starling KL Law TD Self LB Tabas DC Williams DC Paul AH Dantizig (2005) Bioorg Med Chem Lett 15 5526 Occurrence Handle10.1016/j.bmcl.2005.08.075 Occurrence Handle1:CAS:528:DC%2BD2MXhtFOrsL3F
I Zadrozna J Kurkowska H Kruszewska I Mukuch (2000) Farmaco 55 499 Occurrence Handle10.1016/S0014-827X(00)00066-5 Occurrence Handle1:CAS:528:DC%2BD3cXnsl2qsb0%3D
D Raffa G Daidone B Maggio D Scillaci F Plescia L Torta (1999) Farmaco 54 90 Occurrence Handle10.1016/S0014-827X(98)00108-6 Occurrence Handle1:CAS:528:DyaK1MXivFKhtrs%3D
P Calí L Naerum S Mukhija A Hjelmencrantz (2004) Bioorg Med Chem Lett 14 5997 Occurrence Handle10.1016/j.bmcl.2004.09.087 Occurrence Handle1:CAS:528:DC%2BD2cXps1OktLk%3D
E Aiello S Aiello F Mingoia A Bacchi G Pelizzi C Musiu MG Setzu A Pani P La Colla E Marongiu (2000) Bioorg Med Chem 8 2719 Occurrence Handle10.1016/S0968-0896(00)00211-X Occurrence Handle1:CAS:528:DC%2BD3cXot12mtLg%3D
Davenport JD, Dreikorn BA, Elsasser AF (1976) German Patent 2723688
JD Davenport BA Dreikorn AF Elsasser (1978) Chem Abstr 88 132015k
MR Barbachyn GJ Cleek LA Dolak SA Garmon J Morris EP Seest RC Thomas DS Toops W Watt DG Wishka CW Ford GE Zurenko JC Hamel RD Schaadt D Stapert BH Yagi WJ Adams JM Friis JG Slatter JP Sams NL Oien MJ Zaya LC Wienkers MA Wynalda (2003) J Med Chem 46 284 Occurrence Handle10.1021/jm020248u Occurrence Handle1:CAS:528:DC%2BD38XpsVemsr4%3D
MAP Martins W Cunico CMP Pereira AFC Flores HG Bonacorso N Zanatta (2004) Curr Org Synthesis 1 391 Occurrence Handle10.2174/1570179043366611 Occurrence Handle1:CAS:528:DC%2BD2cXnsFGjt7s%3D
MAP Martins CMP Pereira P Beck P Machado S Brondani S Moura MVM Teixeira HG Bonacorso N Zanatta (2003) Tetrahedron Lett 44 6669 Occurrence Handle10.1016/S0040-4039(03)01633-2 Occurrence Handle1:CAS:528:DC%2BD3sXlvFOlsb0%3D
MAP Martins P Beck P Machado S Brondani S Moura N Zanatta HG Bonacorso AFC Flores (2006) J Braz Chem Soc 17 408 Occurrence Handle1:CAS:528:DC%2BD28XjsFCntLs%3D
Sauzem PD, Machado P, Rubin MA, Sant’Anna GS, Faber HB, Souza AH, Mello CF, Beck P, Burrow RA, Bonacorso HG, Zanatta N, Martins MAP (2007) Eur J Med Chem (in press)
MAP Martins CMP Pereira W Cunico S Moura FA Rosa RL Peres P Machado N Zanatta HG Bonacorso (2006) Ultrasonics Sonochem 13 364 Occurrence Handle1:CAS:528:DC%2BD28XjtFGru7s%3D
M Larhed C Moberg A Hallberg (2002) Acc Chem Res 35 717 Occurrence Handle10.1021/ar010074v Occurrence Handle1:CAS:528:DC%2BD38XkslehsLo%3D
A Colla MAP Martins G Clar S Krimmer P Fischer (1991) Synthesis 6 483 Occurrence Handle10.1055/s-1991-26501
MAP Martins GP Bastos HG Bonacorso N Zanatta AFC Flores GM Siqueira (1999) Tetrahedron Lett 40 4309 Occurrence Handle10.1016/S0040-4039(99)00672-3 Occurrence Handle1:CAS:528:DyaK1MXjs12murc%3D
HG Bonacorso MAP Martins SRT Bittencourt RV Lourega N Zanatta AFC Flores (1999) J Fluorine Chem 99 177 Occurrence Handle10.1016/S0022-1139(99)00146-3 Occurrence Handle1:CAS:528:DyaK1MXotVWju7Y%3D
MAP Martins GM Siqueira GP Bastos HG Bonacorso N Zanatta (1996) J Heterocycl Chem 33 1619 Occurrence Handle1:CAS:528:DyaK2sXotFChtw%3D%3D Occurrence Handle10.1002/jhet.5570330612
MA Viviani AM Tortorano L Ajello (2003) Cryptococcus EJ Anaissie MR McGinnis MA Pfaller (Eds) Clinical Mycology Churchil Livingstone New York 240
N Zanatta DM Borchhardt SH Alves HS Coellho AMC Squizani TM Marchi HG Bonacorso MAP Martins (2006) Bioorg Med Chem 14 3174 Occurrence Handle10.1016/j.bmc.2005.12.031 Occurrence Handle1:CAS:528:DC%2BD28Xis1ehs7g%3D
DD Perrin WLF Armarego (1998) Purification of Laboratory Chemicals Pergamon Oxford
National Committee for Clinical Laboratory Standards (2002) Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, 5th edn. NCCLS document M7-A5, Wayne, P. A. National Committee for Clinical Laboratory Standards
S Shadomy M Pfaller (1991) Laboratory studies with antifungal agents: susceptibility tests and quantitation in sody fluids A Ballours WJ Hauster SuffixJr KL Herrmanx HD Isemberg HJ Shadomy (Eds) Manual of Clinical Microbiology EditionNumber5 Americam Society of Microbiology Washington 1173
National Committee for Clinical Laboratory Standards (2002) Reference method for broth dilution antifungal susceptibility testing of yeast: approved standard. NCCLS document M27-A2. Wayne, P. A. National Committee for Clinical Laboratory Standards
Author information
Authors and Affiliations
Corresponding author
Additional information
Correspondence: Marcos A. P. Martins, Núcleo de Química de Heterociclos (NUQUIMHE), Centro de Ciências Naturais e Exatas, Departamento de Química, Universidade Federal de Santa Maria, 97.105-900 Santa Maria, RS, Brazil.
Rights and permissions
About this article
Cite this article
Martins, M., Machado, P., Piovesan, L. et al. Microwave-assisted synthesis and antimicrobial activity of 5-trihalomethyl-3-arylisoxazoles. Monatsh Chem 139, 985–990 (2008). https://doi.org/10.1007/s00706-007-0849-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-007-0849-1