Synthesis, characterization, and antimicrobial activity of some new phosphorus macrocyclic compounds containing pyrazole rings

A simple synthetic method is reported for the preparation of some new phosphorus macrocycles in which the pyrazole rings are appended to a phosphorus atom. The methodology is based on the cyclocondensation reaction of bis(4-formylpyrazolyl) phosphine oxide(1a, 1b) with nitrogen nucleophiles that contain active terminal amino groups. The antimicrobial activities of the synthesized compounds were assayed.

Synthesis, characterization, and antimicrobial activity of some new phosphorus macrocyclic compounds containing pyrazole rings

A simple synthetic method is reported for the preparation of some new phosphorus macrocycles in which the pyrazole rings are appended to a phosphorus atom. The methodology is based on the cyclocondensation reaction of bis(4-formylpyrazolyl) phosphine oxide(1a, 1b) with nitrogen nucleophiles that contain active terminal amino groups. The antimicrobial activities of the synthesized compounds were assayed.

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  • Berlicki, L.; Rudzinska, E.; Mlynarz, P.; Kafarski, P. Curr. Org. Chem. 2006, 11, 1593–1609.
  • Llobet, A.; Reibenspies, J.; Martell, A. E. Inorg. Chem. 1994, 33, 5946–5951.
  • Ross, E.; Motekaitis, R. J.; Martell, A. E. Inorg. Chim. Acta 1999, 286, 55–61.
  • Hay, E. W.; Clifford, T.; Richens, D. T.; Lightfoot, P. Polyhedron 2000, 19, 1485–1492.
  • Arion, V. B.; Bill, E.; Reetz, M. T.; Goddart, R.; Stoeckigt, D.; Massau M.; Levitsky, V. Inorg. Chim. Acta 1998, 282, 61–70.
  • Kuolov, A. V.; Mahoney, J. M.; Smith, B. D. Org. Biomol. Chem. 2003, 1, 27–29.
  • Collinson, S. R.; Fenton, D. E. Coord. Chem. Rev. 1996, 148, 19–40.
  • Adams, N. A.; Bailey, S. R.; Collinson, D. E.; Fenton, J. C.; Hawley, S. J.; Kitchen, J. Organomet. Chem. 1998, 550, 7–20.
  • Antunes, P.; Delgado, R.; Drew, M. G. B.; Felix, V.; Maecke, H. Inorg. Chem. 2007, 46, 3144–3153.
  • Li, R.; Delgado, F.; Drew, M. G. B.; Felix, V. Dalton Trans. 2006, 45, 5396–5403.
  • Caminade, A. M.; Majoral, J. P. Chem. Rev. 1994, 94, 1183–1213.
  • Dutasta, J. P.; Simon, P. Tetrahedron Lett. 1987, 28, 3577–3580.
  • Diederich, F. Angew. Chem. Int. Ed. Eng. 1988, 27, 362–386.
  • Tucker, A. J.; Knobler, C. B.; Trueblood, K. N.; Cram, J. D. J. Am. Chem. Soc. 1989, 111, 3688–3699.
  • Fages, F.; Desvergue, J. P.; Kotzbahibert, F.; Lehn, J. M.; Marson, P.; Albrechtgary, A. M.; Bouaslarent, H.; Aljoubloeh, M. J. Am. Chem. Soc. 1989, 111, 8672–8680.
  • Wallon, A.; Peter-Katinic, J.; Werner, W. M.; Vogtle, F. Chem. Ber. 1990, 123, 375–379.
  • Seward, E. M.; Hopkins, R. B.; Sauerer, W.; Tam, S. W.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 1783–1790. Brelow, R.; Greenspoon, N.; Guo, T.; Zarzycki, R. J. Am. Chem. Soc. 1989, 111, 8296–8297.
  • Sheridan, R. E.; Whitlock, H. W. J. Am. Chem. Soc. 1988, 110, 4071–4073.
  • Witschel, M. Bioorg. Med. Chem. 2009, 17, 4221–4229.
  • Lahm, G. P.; Stevenson, T. M.; Selby, T. P.; Freudenberger, J. H.; Cordova, D.; Flexner, L.; Bellin, C. A.; Dubas, C. M.; Smith, B. K.; Hughes, K. A.; Hollingshaus, J. G.; Clark, C. E.; Benner, E. A. Bioorg. Med. Chem. Lett. 2007, 17, 6274–6279.
  • Abdel-Ghaffar, S. A.; Ali, T. E.; El-Mahdy, K. M.; Abdel-Karim, S. M. Eur. J. Chem. 2011, 2, 25–35.
  • Audrieth, L. F.; Scott, E. S.; Kippur, P. S. J. Org. Chem. 1954, 19, 733–741.
  • Shukla, J. S.; Zaidi, M. G. H. Asian J. Chem. 1993, 5, 253–260.
  • Borisova, N. E.; Reshetova, M. D.; Ustynuk, Y. A. Chem. Rev. 2007, 107, 46–79.
  • Bullita, E.; Casellato, U.; Ossola, F.; Tomasin, P.; Vigato, P. A.; Russo, U. Inorg. Chem. Acta 1999, 287, 117–133. Stotz, R. W.; Stoufer, R. C. Chem. Commun. 1970, 1682–1683.
  • Adams, H.; Bailey, N. A.; Fenton, D. E.; Moss, S.; Rodrigues de Barbarin, C. O.; Jones, G. J. Chem. Soc. Dalton Trans. 1986, 693–699.
  • Corbridge, D. E. C. Phosphorus: An Outline of its Chemistry, Biochemistry and Uses, 5th ed., Elsevier, Amsterdam, 19 Babin, Y. V.; Gavrikov, A. V.; Ustynyuk, Y. A. Mendeleev Commun. 2008, 18, 12–13.
  • Mamaev, V. M.; Prisyajnuk, A. V.; Laikov, D. N.; Logutenko, L. S.; Babin, Y. V. Russ. J. Phys. Chem. 2001, 75, 581–588.
  • Mamaev, V. M.; Prisyajnuk, A. V.; Logutenko, L. S.; Babin, Y. V. Mendeleev Commun. 2001, 11, 221–222.
  • Rahman, A. U.; Choudhary, M. I.; Thomsen, W. J. Bioassay Techniques for Drug Development, Harwood Academic Publishers, Amsterdam, 2001.
  • Khan, K. M.; Saify, Z. S.; Zeesha, A. K.; Ahmed, M.; Saeed, M.; Schick, M.; Bkohlbau, H. J.; Voelter, W. ArzneimForsch./Drug Res. 2000, 50, 915–922.
  • Mishra, D.; Patnaik, S.; Rath, C. C.; Dash, S. K.; Mishra, R. K.; Patnaik, U. Indian J. Pharm. Sci. 2002, 64, 256–259.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

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Synthesis, characterization, and antimicrobial activity of some new phosphorus macrocyclic compounds containing pyrazole rings

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A new method for calculating the vibration-rotation-tunneling spectra of molecular clusters and its application to the water dimer

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