Download PDF
Synthesis 2014; 46(11): 1511-1517
DOI: 10.1055/s-0033-1340978
paper
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Synthesis of Biotin Conjugates with Quinolone Antibiotics via Amino Acids

Siva S. Panda
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA   Fax: +1(352)3929199   Email: panda@chem.ufl.edu   Email: katritzky@chem.ufl.edu
,
Roman N. Naumov
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA   Fax: +1(352)3929199   Email: panda@chem.ufl.edu   Email: katritzky@chem.ufl.edu
,
Abdullah M. Asiri
b   Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia
c   Center for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah 21589, Saudi Arabia
,
Alan R. Katritzky*
a   Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA   Fax: +1(352)3929199   Email: panda@chem.ufl.edu   Email: katritzky@chem.ufl.edu
b   Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia
› Author Affiliations
Further Information

Publication History

Received: 06 January 2014

Accepted after revision: 20 February 2014

Publication Date:
02 April 2014 (online)

    Permissions and Reprints All articles of this category


Abstract

Benzotriazole-activated biotin was utilized as a versatile building block for the efficient and convenient synthesis of novel biotin conjugates with quinolone antibiotics via amino acid linkers under microwave irradiation. The products are obtained in yields of 70–91% with retention of chirality.

Key words

biotin - vitamins - antibiotics - amino acid - benzotriazole method - microwave-assisted reaction

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

  • References

  • 1 Camporeale G, Zempleni J. Biotin . In Present Knowledge in Nutrition . 9th ed.; Bowman BA, Russell RM. ILSI Press; Washington DC: 2006: 314
    Google Scholar
  • 2 Rodriguez-Melendez R, Zempleni J. J. Nutr. Biochem. 2003; 14: 680
    Crossref
  • 3 Zempleni J. Annu. Rev. Nutr. 2005; 25: 175
    Crossref
  • 4 Fernandez-Mejia C. J. Nutr. Biochem. 2005; 16: 424
    Crossref
  • 5 Larrieta E, Vega-Monroy ML. L, Vital P, Aguilera A, German MS, Hafidi ME, Fernandez-Mejia C. J. Nutr. Biochem. 2012; 23: 392
    Crossref
  • 6 Bain SD, Newbrey JW, Watkins BA. Poult. Sci. 1988; 67: 590
    Crossref
  • 7 Báez-Saldaña A, Ortega E. J. Nutr. 2004; 134: 1970
  • 8 Báez-Saldaña A, Gutiérrez-Ospina G, Chimal-Monroy J, Fernandez-Mejia C, Saavedra R. Eur. J. Nutr. 2009; 48: 137
    Crossref
  • 9 Báez-Saldaña A, Díaz G, Espinoza B, Ortega E. Am. J. Clin. Nutr. 1998; 67: 431
  • 10 Watanabe T, Endo A. Teratology 1990; 42: 295
    Crossref
  • 11 Takeshi R, Taniguchi A, Ebara S, Fukui T, Watanabe T. J. Nutr. 2008; 138: 680
  • 12 Rodríguez-Meléndez R, Cano S, Méndez ST, Velázquez A. J. Nutr. 2001; 131: 1909
  • 13 Pacheco-Alvarez D, Solórzano-Vargas RS, Gravel RA, Cervantes-Roldán R, Velázquez A, León-Del-Río A. J. Biol. Chem. 2004; 279: 52312
    Crossref
  • 14 Chauhan J, Dakshinamurti K. J. Biol. Chem. 1991; 266: 10035
  • 15 Romero-Navarro G, Cabrera-Valladares G, German MS, Matschinsky FM, Velazquez A, Wang J. Endocrinology 1999; 140: 4595
  • 16 Sone H, Ito M, Sugiyama K, Ohneda M, Maebashi M, Furukawa Y. J. Nutr. Biochem. 1999; 10: 237
    Crossref
  • 17 Hugo WB, Bowen JG, Davidson JR. J. Pharm. Pharmacol. 1971; 23: 69
    Crossref
  • 18 Huttunen KM, Raunio H, Rautio J. Pharmacol. Rev. 2011; 63: 750
    Crossref
  • 19 Rasheed A, Kumar CK. A, Mishra A. J. Enzyme Inhib. Med. Chem. 2011; 26: 688
    Crossref
  • 20 Aboul-Fadl T, Fouad EA. Pharmazie 1996; 51: 30
  • 21 Taori A, Nema R, Kohli DV, Uppadhyay RK. Arch. Pharm. Res. 1991; 14: 48
    Crossref
  • 22 Mishra A, Veerasamy R, Jain PK, Dixit VK, Agrawal RK. J. Braz. Chem. Soc. 2008; 19: 89
  • 23 Simplicio AL, Clancy JM, Gilmer JF. Molecules 2008; 13: 519
    CrossrefPubMed
  • 24 Panda SS, Bajaj K, Meyers MJ, Sverdrup FM, Katritzky AR. Org. Biomol. Chem. 2012; 10: 8985
    Crossref
  • 25 Panda SS, Ibrahim MA, Kucukbay H, Meyers MJ, Sverdrup FM, El-Feky SA, Katritzky AR. Chem. Biol. Drug Des. 2013; 82: 361
    Crossref
  • 26 El-Nachef C, Bajaj K, Koblick J, Katritzky AR. Eur. J. Org. Chem. 2012; 4412
  • 27 Panda SS, El-Nachef C, Bajaj K, Al-Youbi AO, Oliferenko A, Katritzky AR. Chem. Biol. Drug Des. 2012; 80: 821
    Crossref