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Synthesis of novel 3-[5-ethyl-2-(2-phenoxy-ethyl)-pyridin]-5-substituted isoxazoline libraries via 1,3-dipolar cycloaddition and evaluation of antimicrobial activities

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Abstract

A series of novel 3-[5-ethyl-2-(2-phenoxy-ethyl)-pyridin]-5-substituted isoxazolines were synthesized via 1,3-dipolar cycloaddition of in situ generated nitrile oxide from 4-[2-(5-ethylpyridyl)-ethoxy]-benzaldoxime with alkenes to obtain new heterocyclic libraries containing a pyridine moiety in addition to the isoxazoline ring. The newly synthesized compounds were screened for their antimicrobial activity and were compared with standard drugs. The compounds demonstrated potent to weak antimicrobial activity. Of the compounds studied, compounds 3c and 3f showed significant antibacterial as well as antifungal activity. Compounds 3e and 3g showed moderate activity. The title compounds represent a novel class of potent antimicrobial agents.

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References

  • Basappa M, Sadashiva P, Mantelingu K, Nanjunda Swamy S, Rangappa KS (2003) Solution-phase synthesis of novel Δ2-isoxazoline libraries via 1,3-dipolar cycloaddition and their antifungal properties. Bioorg Med Chem 11:4539

    Article  PubMed  CAS  Google Scholar 

  • Basappa M, Kumar S, Nanjunda Swamy S, Mahendra M, Shashidhara Prasad J, Viswanath BS, Rangappa KS (2004) Novel δ2-isoxazolines as group II phospholipase A2 inhibitors. Bioorg Med Chem Lett 14:3679

    Article  PubMed  CAS  Google Scholar 

  • Conti P, Dallanoce C, Amici MD, Micheli CD, Klotz KN (1998) Synthesis of new Δ2-isoxazoline derivatives and their pharmacological characterization as β-adrenergic receptor antagonists. Bioorg Med Chem 16:401

    Article  Google Scholar 

  • Gaonkar SL, Yathirajan HS, Lokanatharai KM, Nagaraj B, Bolte M (2005) 4-[2-(5-Ethylpyridin-2-yl)ethoxy]benzaldehyde oxime. Acta Cryst E 61:751

    Article  CAS  Google Scholar 

  • Gaonkar SL, Rai KML, Prabhuswamy B (2006) Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5-substituted-1,3,4-oxadiazoles. Eur J Med Chem 41: 841

    Article  PubMed  CAS  Google Scholar 

  • Groutas WC, Chong LS, Epp JB, Venkataraman R, Brubaker MJ, Stanga MA, Kim EH, Keller CE (1992) Inhibition of human leukocyte elastase and cathepsin G by isoxazoline derivatives. Bioorg Med Chem Lett 2:1571

    Article  CAS  Google Scholar 

  • Groutas WC, Venkataraman R, Chong LS, Yoder JE, Epp JB, Stanga MA, Kim EH (1995) Isoxazoline derivatives as potential inhibitors of the proteolytic enzymes human leukocyte elastase, cathepsin G and proteinase 3: a structure-activity relationship study. Bioorg Med Chem 3:125

    Article  PubMed  CAS  Google Scholar 

  • Hassner A, Lokanatha Rai KM (1989) A new method for the generation of nitrile oxides and its application to the synthesis of 2-isoxazolines. Synthesis 57

  • Kai H, Matsumoto H, Hattori N, Takase A, Fujiwara T, Sugimoto H (2001) Anti-influenza virus activities of 2-Alkoxyimino-N-(2-isoxazolin-3-ylmethyl)acetamides. Bioorg Med Chem 299 Lett 11:1997

    Article  CAS  Google Scholar 

  • Lednicer D, Mitscher LA (1998a) The organic chemistry of drug synthesis: Volume 1. John Wiley & Sons, New York: pp: 253–256

  • Lednicer D, Mitscher LA (1998b) The organic chemistry of drug synthesis: Volume 2. John Wiley & Sons, New York: pp. 278–283

  • Lednicer D, Mitscher LA (1998c) The organic chemistry of drug synthesis: Volume 3. John Wiley & Sons, New York: pp: 145–152

  • Lemriss S, Marquet B, Ginestet H, Lefeuvre L, Fassouane A, Boiron P (2003) Screening of new antifungal compounds in a collection of chemical products. J Mycol Med 13:189

    Google Scholar 

  • Levin JI, Chan PS, Coupet J, Bailey TK, Vice G, Thibault L, Lai F, Venkatesan AM, Cobuzzi (1994) A 6-isoxazolinyl and isoxazolidinyl substituted quinazolinones as angiotensin II receptor antagonists. Bioorg Med Chem Lett 4:1703

    Google Scholar 

  • Meguro K, Fujita T (1986) Process for preparing thiazolidine derivatives. Eur Patent 193256

  • Sielecki TM, Liu J, Mousa SA, Racanelli AL, Hausner EA, Wexler RR, Olson RE (2001) Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists. Bioorg Med Chem Lett 11:2201

    Article  PubMed  CAS  Google Scholar 

  • Srivastava S, Bajpai LK, Batra S, Bhaduri AP, Maikhuri JP, Gupta G, Dhar JD (1999) In search of new chemical entities with spermicidal and anti-HIV activities. Bioorg Med Chem 7:2607

    Article  PubMed  CAS  Google Scholar 

  • Zgoda JR, Porter JR (2001) A convenient Microdilution method for screening natural products against bacteria and fungi. Pharm Biol 39:221

    Article  CAS  Google Scholar 

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Acknowledgments

SLG thanks M/S Jubilant Organosys Ltd., Nanjangud for permission to carry out the research work at University of Mysore.

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Correspondence to K.M. Lokanatha Rai.

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Gaonkar, S., Rai, K.L. & Prabhuswamy, B. Synthesis of novel 3-[5-ethyl-2-(2-phenoxy-ethyl)-pyridin]-5-substituted isoxazoline libraries via 1,3-dipolar cycloaddition and evaluation of antimicrobial activities. Med Chem Res 15, 407–417 (2007). https://doi.org/10.1007/s00044-006-0015-z

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  • DOI: https://doi.org/10.1007/s00044-006-0015-z

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