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Synthesis 2006(5): 807-812  
DOI: 10.1055/s-2006-926339
PAPER
© Georg Thieme Verlag Stuttgart · New York

Rapid Microwave-Assisted Syntheses of Derivatives of HIV-1 Entry Inhibitors

Chris McFarlanda, David A. Vicic*a, Asim Kumar Debnath*b
a Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, USA
e-Mail: dvicic@uark.edu;
b Laboratory of Molecular Modeling and Drug Design of the Lindsley F. Kimball Research Institute of the New York Blood Center, 310 E. 67th St., New York, NY 10021, USA
Further Information

Publication History

Received 20 September 2005
Publication Date:
07 February 2006 (online)

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Abstract

The direct amidation of esters with 4-amino-2,2,6,6-tetramethylpiperidine was achieved by computer-controlled microwave irradiation in toluene. The microwave protocol allowed the new amides to be prepared in three hours rather than the three days required by traditional thermal methods.

Key words

microwave-assisted synthesis - HIV - amidation - CCR5 - gp120

    References

  • 1 Hunter E. Viral Entry and Receptor, In Retroviruses   Coffin JM. Hughes SH. Varmus HE. Cold Spring Harbor Laboratory Press; N.Y.: 1997.  p.71-119  
    Google Scholar
  • 2 Sattentau QJ. Moore JP. J. Exp. Med.  1991,  174:  407 
    CrossrefGoogle Scholar
  • 3 Sattentau QJ. Moore JP. Vignaux F. Traincard F. Poignard P. J. Virol.  1993,  67:  7383 
    Google Scholar
  • 4 Moore JP. Sweet RW. Perspect. Drug Discov. Des.  1993,  1:  235 
    CrossrefGoogle Scholar
  • 5 Berger EA. AIDS  1997,  11 (Suppl A):  S3 
    Google Scholar
  • 6 Berger EA. Adv. Exp. Med. Biol.  1998,  452:  151 
    Google Scholar
  • 7 Dragic T. Litwin V. Allaway GP. Martin SR. Huang Y. Nagashima KA. Cayanan C. Maddon PJ. Koup RA. Moore JP. Paxton WA. Nature (London)  1996,  381:  667 
    CrossrefPubMedGoogle Scholar
  • 8 Moore JP. Science (Washington, D.C.)  1997,  276:  51 
    CrossrefGoogle Scholar
  • 9 Sullivan N. Sun Y. Sattentau Q. Thali M. Wu D. Denisova G. Gershoni J. Robinson J. Moore J. Sodroski J. J. Virol.  1998,  72:  4694 
    Google Scholar
  • 10 Chang D.-K. Cheng S.-F. Trivedi VD. J. Biol. Chem.  1999,  274:  5299 
    CrossrefGoogle Scholar
  • 11 Freed EO. Myers DJ. Risser R. Proc. Natl. Acad. Sci. U.S.A.  1990,  87:  4650 
    CrossrefGoogle Scholar
  • 12 Melikyan GB. Markosyan RM. Hemmati H. Delmedico MK. Lambert DM. Cohen FS. J. Cell Biol.  2000,  151:  413 
    CrossrefGoogle Scholar
  • 13 Capon DJ. Ward RH. Annu. Rev. Biochem.  1991,  9:  649 
    Google Scholar
  • 14 Kwong PD. Wyatt R. Robinson J. Sweet RW. Sodroski J. Hendrickson WA. Nature (London)  1998,  393:  648 
    CrossrefGoogle Scholar
  • 15 Wyatt R. Kwong PD. Desjardins E. Sweet RW. Robinson J. Hendrickson WA. Sodroski JG. Nature (London)  1998,  393:  705 
    CrossrefGoogle Scholar
  • 16 Carter WA. Brodsky I. Pellegrino MG. Henriques HF. Parenti DM. Schulof RS. Robinson WE. Volsky DJ. Paxton H. Kariko K. Suhadolnik RJ. Strayer DR. Lewin M. Einck L. Simon GL. Scheib RG. Montefiori DC. Mitchell WM. Paul D. Meyer WA. Reichenbach N. Gillespie DH. Lancet  1987,  1286 
    Google Scholar
  • 17 Wu L. Gerard NP. Wyatt R. Choe H. Parolin C. Ruffing N. Borsetti A. Cardoso AA. Desjardin E. Newman W. Gerard C. Sodroski J. Nature (London)  1996,  384:  179 
    CrossrefGoogle Scholar
  • 18 Kwong PD. Wyatt R. Majeed S. Robinson J. Sweet RW. Sodroski J. Hendrickson WA. Structure  2000,  8:  1329 
    CrossrefGoogle Scholar
  • 19 Chen B. Vogan EM. Gong H. Skehel JJ. Wiley DC. Harrison SC. Nature (London)  2005,  433:  834 
    CrossrefGoogle Scholar
  • 20 Chen B. Vogan EM. Gong H. Skehel JJ. Wiley DC. Harrison SC. Structure (Cambridge, MA, U.S.)  2005,  13:  197 
    CrossrefGoogle Scholar
  • 21 Lin PF. Blair W. Wang T. Spicer T. Guo Q. Zhou N. Gong YF. Wang HG. Rose R. Yamanaka G. Robinson B. Li CB. Fridell R. Deminie C. Demers G. Yang Z. Zadjura L. Meanwell N. Colonno R. Proc. Natl. Acad. Sci. U.S.A.  2003,  100:  11013 
    CrossrefGoogle Scholar
  • 22 Wang T. Zhang Z. Wallace OB. Deshpande M. Fang H. Yang Z. Zadjura LM. Tweedie DL. Huang S. Zhao F. Ranadive S. Robinson BS. Gong YF. Ricarrdi K. Spicer TP. Deminie C. Rose R. Wang HG. Blair WS. Shi PY. Lin PF. Colonno RJ. Meanwell NA. J. Med. Chem.  2003,  46:  4236 
    CrossrefGoogle Scholar
  • 23 Zhao Q. Ma L. Jiang S. Lu H. Liu S. He Y. Strick N. Neamati N. Debnath AK. Virology  2005,  339:  213 
    CrossrefGoogle Scholar
  • 24 Waltman AW. Grubbs RH. Organometallics  2004,  23:  3105 
    CrossrefGoogle Scholar
  • 25 Molteni V. Ellis DA. Curr. Org. Synth.  2005,  2:  333 
    CrossrefGoogle Scholar
  • 26 Strauss CR. Chem. Aust.  2005,  72:  9 
    Google Scholar
  • 27 de la Hoz A. Diaz-Ortiz A. Moreno A. Chem. Soc. Rev.  2005,  34:  164 
    CrossrefPubMedGoogle Scholar
  • 28 Kappe CO. Angew. Chem. Int. Ed.  2004,  43:  6250 
    CrossrefPubMedGoogle Scholar
  • 29 Ersmark K. Larhed M. Wannberg J. Curr. Opin. Drug Discov. Dev.  2004,  7:  417 
    Google Scholar
  • 30 De La Hoz A. Diaz-Ortiz A. Moreno A. Curr. Org. Chem.  2004,  8:  903 
    CrossrefGoogle Scholar
  • 31 Loupy A. C. R. Chim.  2004,  7:  103 
    CrossrefGoogle Scholar
  • 32 Nuechter M. Ondruschka B. Bonrath W. Gum A. Green Chem.  2004,  6:  128 
    CrossrefGoogle Scholar
  • 33 Srivastava KP. Chemistry  2003,  1:  215 
    Google Scholar
  • 34 Alexandre F.-R. Domon L. Frere S. Testard A. Thiery V. Besson T. Mol. Diversity  2003,  7:  273 
    CrossrefGoogle Scholar
  • 35 Hajek M. In Microwaves in Organic Synthesis   Loupy A. Wiley-VCH; Weinheim: 2002.  p.345 
    Google Scholar
  • 36 Roberts BA. Strauss CR. Acc. Chem. Res.  2005,  38:  653 
    CrossrefPubMedGoogle Scholar
37

Crystallographic data (excluding structure factors) for compound 2 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 286628. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax:+44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].