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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 17
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Original Articles

Synthesis in Water and Antimicrobial Activity of 5-Trichloromethyl-4,5-dihydroisoxazoles

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Pages 2326-2336 | Received 18 Apr 2012, Published online: 03 Jun 2013

REFERENCES

  • Budzik , B. W. ; Evans , K. A. ; Wisnoski , D. D. ; Jin , J. ; Rivero , R. A. ; Szewczyk , G. R. ; Jayavickreme , C. ; Molcol , D. L. ; Yu , H. Synthesis and structure–activity relationships of a series of 3-aryl-4-isoxazolecarboxamides as a new class of TGR5 agonists . Bioorg. Med. Chem Lett. 2010 , 20 , 1363 – 1367 .
  • Peifer , C. ; Abadleh , M. ; Bischof , J. ; Hauser , D. ; Schattel , V. ; Hirners , H. ; Knippschil , U. ; Laufer , S. 3,4-Diaryl-isoxazoles and -imidazoles as potent dual inhibitors of p38α mitogen activated protein kinase and casein kinase 1δ . J. Med. Chem. 2009 , 52 , 7618 – 7630 .
  • Zhan , P. ; Li , D. ; Chen , X. ; Liu , X. ; De Clercq , E. Functional roles of azoles motif in anti-HIV agents . Curr. Med. Chem. 2011 , 18 , 29 – 46 .
  • Yadav , M. R. ; Sabale , P. M. ; Giridhar , R. ; Zimmer , C. ; Haupenthal , J. ; Hartmann , R. W. Synthesis of some novel androstanes as potential aromatase inhibitors . Steroids 2011 , 76 , 464 – 470 .
  • Upadhyay , A. ; Gopal , M. ; Srivastava , C. ; Pandey , N. D. Isoxazole derivatives as a potential insecticide for managing Callosobruchus chinensis . J. Pest. Sci. 2010 , 35 , 464 – 469 .
  • Kumar , D. ; Kumar , N. M. ; Patel , G. ; Gupta , S. ; Varma , R. S. A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water . Tetrahedron Lett. 2011 , 52 , 1983 – 1986 .
  • Rogozinska , M. ; Adamkiewcz , A. ; Mlynarski , J. Efficient “on water” organocatalytic protocol for the synthesis of optically pure warfarin anticoagulant . Green Chem. 2011 , 13 , 1155 – 1157 .
  • Calderone , R. A. ; Fonzi , W. A. Virulence factors of Candida albicans . Trends Microbiol. 2001 , 9 , 327 – 335 .
  • Borg , M. ; Ruchel , R. Expression of extracellular acid proteinase by proteolytic Candida spp. during experimental infection of oral mucosa . Infect. Immun. 1988 , 56 , 626 – 631 .
  • Mitchell , T. G. ; Perfect , J. R. Cryptococcosis in the era of AIDS—100 years after the discovery of Cryptococcus neoformans . Clin. Microbiol. Rev. 1995 , 8 , 515 – 548 .
  • Otto , M. Quorum-sensing control in Staphylococci—a target for antimicrobial drug therapy? FEMS Microbiol. Lett. 2004 , 241 , 135 – 141 .
  • Dowell , S. F. Antimicrobial resistance: Is it really that bad? Semin. Pediatr. Infect. Dis. 2004 , 15 , 99 – 104 .
  • Coast , J. ; Smith , R. D. Solving the problem of antimicrobial resistance: Is a global approach necessary? Drug Dis. Today 2003 , 8 , 1 – 2 .
  • Canuto , M. M. ; Rodero , F. G. Antifungal drug resistance to azoles and polyenes . Lancet Infect. Dis. 2002 , 2 , 550 – 563 .
  • Taylor , P. W. ; Stapleton , P. D. ; Luzio , J. P. New ways to treat bacterial infections . Drug Disc. Today , 2002 , 7 , 1086 – 1091 .
  • Flores , A. F. C. ; Flores , D. C. ; Piovesan , L. A. ; Malavolta , J. L. ; Martins , M. A. P. Heterocyclization of omega-bromo-2-trichloroacetyl cycloalkanones to isoxazole derivatives. Synth. Commun. 2009, 39, 1893–1902.
  • Gressler , V. ; Moura , S. ; Flores , A. F. C. ; Flores , D. C. ; Colepicolo , P. ; Pinto , E. Antioxidant and antimicrobial properties of 2-(4,5-dihydro-1H-pyrazol-1-yl)-pyrimidine and 1-carboxamidino-1H-pyrazole derivatives . J. Braz. Chem Soc. 2010 , 21 , 1477 – 1483 .
  • Flores , A. F. C. ; Flores , D. C. ; Oliveira , G. ; Pizzuti , L. ; Martins , M. A. P. ; Bonacorso , H. G. Efficient synthesis of new 1-[alkyl(aryl)]-5-(3,3,3-trihalo-2-oxopropylidene)pyrrolidin-2-ones . J. Braz. Chem Soc. 2008 , 19 , 84 – 93 .
  • Flores , A. F. C. ; Pizzuti , L. ; Piovesan , L. A. ; Flores , D. C. ; Malavolta , J. L. ; Pereira , C. M. P. Tetrahedron Lett. 2010 , 51 , 4908 – 4910 .
  • Martins , M. A. P. ; Machado , P. ; Piovesan , L. A. ; Flores , A. F. C. ; de Campos , M. M. A. ; Scheidt , C. ; Bonacorso , H. G. ; Zanatta , N. Microwave-assisted synthesis and antimicrobial activity of 5-trihalomethyl-3-arylisoxazoles . Monatsh. Chem. 2008 , 139 , 985 – 990 .
  • Flores , A. F. C. ; Brondani , S. ; Zanatta , N. ; Martins , M. A. P. Synthesis of 1,1,1-trihalo-4-methoxy-4-[2-heteroaryl]-3-buten-2-ones, the corresponding butan-1,3-dione and azole derivatives . Tetrahedron Lett. 2002 , 43 , 8701 – 8705 .
  • Kumar , V. ; Aggarwal , R. ; Singh , S. P. The reaction of hydroxylamine with aryl trifluoromethyl-β-diketones: Synthesis of 5-hydroxy-5-trifluoromethyl-Δ2-isoxazolines and their dehydration to 5-trifluoromethylisoxazoles . J. Fluorine Chem. 2006 , 127 , 880 – 888 .
  • Okabayashi , K. ; Hasegawa , A. ; Watanabe , T. Microreview: Capsule-associated genes of Cryptococcus neoformans . Mycopathologia 2007 , 163 , 1 – 8 .
  • Lee , A. ; Toffaletti , D. L. ; Tenor , J. ; Soderblom , E. J. ; Thompson , J. W. ; Moseley , M. A. ; Price , M. ; Perfect , J. R. Survival defects of Cryptococcus neoformans mutants exposed to human cerebrospinal fluid result in attenuated virulence in an experimental model of meningitis . Infect. Immun. 2010 , 78 , 4213 – 4225 .
  • National Committee for Clinical Laboratory Standards. Document M7-A5, National Committee for Clinical Laboratory Standards: Wayne, PA, 2002 .
  • Farrugia , L. J. ORTEP-3 for Windows—A version of ORTEP-III with a graphical user interface . J. Appl. Cryst. 1997 , 30 , 565 .
  • Martins , M. A. P. ; Beck , P. ; Cunico , W. ; Pereira , C. M. P. ; Sinhorin , A. P. ; Blanco , R. F. ; Peres , R. ; Bonacorso , H. G. ; Zanatta , N. Microwave-assisted synthesis of 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles . Tetrahedron Lett. 2002 , 43 , 7005 – 7008 .
  • Martins , M. A. P. ; Pereira , C. M. P. ; Cunico , W. ; Moura , S. ; Rosa , F. A. ; Peres , R. L. ; Machado , P. ; Bonacorso , H. G. ; Zanatta , N. Ultrasound-promoted synthesis of 5-hydroxy-5-trihalomethyl-4,5-dihydroisoxazoles and β-enamino trihalomethyl ketones in water . Ultrasound Sonochem. 2006 , 13 , 364 – 370 .

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