Eight pyrazolo[3,4-b]pyridine derivatives have been synthesized by Friedländer condensation of 5-aminopyrazole-4-carbaldehyde with active methylene compounds in basic medium. These compounds have been screened for their antibacterial activity against two Gram-negative and two Gram-positive bacterium. Pyrazolopyridines having the carboxamide group at the 5-position showed moderate to good activity against P. aeruginosa, E. coli, S. pneumoniae, and B. cereus.
Similar content being viewed by others
References
S. J. Brickner, D. K. Hutchinson, M. R. Barbachyn, P. R. Manninen, D. A. Ulanowicz, S. A. Garmon, K. C. Grega, S. K. Hendges, D. S. Toops, C. W. Ford, and G. E. Zurenko., J. Med. Chem., 39, 673 (1996).
M. J. Genin, D. A. Allwine, D. J. Anderson, M. R. Barbachyn, D. E. Emmert, S. A. Garmon, D. R. Graber, K. C. Grega, J. B. Hester, D. K. Hutchinson, J. Morris, R. J. Reischer, C. W. Ford, G. E. Zurenko, J. C. Hamel, R. D. Schaadt, D. Stapert, and B. H. Yagi, J. Med. Chem., 43, 953 (2000).
W. Stadlbauer, in: R. Neier (editor), Science of Synthesis: Houben-Weyl Methods of Molecular Transformation, Thieme, Stuttgart, New York, Vol. 12, p. 227.
M. N. Jachak, A. B. Avhale, C. D. Tantak, R. B. Toche, C. Reidlinger, and W. Stadlbauer, J. Heterocycl. Chem., 42, 1311 (2005).
J. B. Patel, J. B. Malick, A. I. Salama, and M. E. Goldberg, Pharmacol. Biochem. Behav., 23, 675 (1985).
L. Bettinetti, K. Schlotter, H. Hübner, and P. Gmeiner, J. Med. Chem., 45, 4594 (2002).
S. Löber, H. Hübner, W. Utz, and P. Gmeiner, J. Med. Chem., 44, 2691 (2001).
S. Kuroda, A. Akahane, H. Itani, S. Nishimura, K. Durkin, Y. Tenda, and K. Sakane, Bioorg. Med. Chem., 8, 55 (2000).
T. Tuccinardi, S. Schenone, F. Bondavalli, C. Brullo, O. Bruno, L. Mosti, A. T. Zizzari, C. Tintori, F. Manetti, O. Ciampi, M. L. Trincavelli, C. Martini, A. Martinelli, and M. Botta, ChemMedChem., 3, 898 (2008).
B. A. Johns, K. S. Gudmundsson, E. M. Turner, S. H. Allen, V. A. Samano, J. A. Ray, G. A. Freeman, F. L. Boyd, C. J. Sexton, D. W. Selleseth, K. L. Creech, and K. R. Moniri, Bioorg. Med. Chem., 13, 2397 (2005).
P. K. Sharma, K. Singh, S. Kumar, P. Kumar, S. N. Dhawan, S. Lal, H. Ulbrich, and G. Dannhardt, Med. Chem. Res., DOI 10.1007/s00044-010-9312-7.
T. Irikura, K. Nishino, S. Suzue, and T. Ikeda, Eur. Pat. Appl. EP0118916. ep.espacenet.com
B. M. Lynch, M. A. Khan, H. C. Teo, and F. Pedrotti, Can. J. Chem., 66, 420 (1988).
G. Lavecchia, S. Berteina-Raboin, and G. Guillaumet, Tetrahedron Lett., 45, 6633 (2004).
R. V. Fucini, E. J. Hanan, M. J. Romanowski, R. A. Elling, W. Lew, K. J. Barr, J. Zhu, J. C. Yoburn, Y. Liu, B. T. Fahr, J. Fan, Y. Lu, P. Pham, I. C. Choong, E. C. Van der Porten, M. Bui, H. E. Purkey, M. J. Evanchik, and W. Yang, Bioorg. Med. Chem. Lett., 18, 5648 (2008).
T. J. Tucker, J. T. Sisko, R. M. Tynebor, T. M. Williams, P. J. Felock, J. A. Flynn, M.-T. Lai, Y. Liang, G. McGaughey, M. Liu, M. Miller, G. Moyer, V. Munshi, R. Perlow-Poehnelt, S. Prasad, J. C. Reid, R. Sanchez, M. Torrent, J. P. Vacca, B.-L. Wan, and Y. Yan, J. Med. Chem., 51 , 6503 (2008).
Y.-L. Zhong, M. G. Lindale, and N. Yasuda, Tetrahedron Lett., 50, 2293 (2009).
N. A. Hamdy and A. M. Gamal-Eldeen, Eur. J. Med. Chem., 44, 4547 (2009).
M. Chioua, A. Samadi, E. Soriano, O. Lozach, L. Meijer, and J. Marco-Contelles, Bioorg. Med. Chem. Lett., 19, 4566 (2009).
Díaz-Ortiz, A. de la Hoz, and F. Langa, Green Chem., 2, 165 (2000).
M. Suzuki, H. Iwasaki, Y. Fujikawa, M. Sakashita, M. Kitahara, and R. Sakoda, Bioorg. Med. Chem. Lett., 11, 1285 (2001).
J. Quiroga, B. Insuasty, A. Hormaza, D. Gamenara, L. Domínguez, and J. Saldaňa, J. Heterocycl. Chem., 36, 11 (1999).
X. Zou, S. Tu, F. Shi, J. Xu, ARKIVOC, ii, 130 (2006).
L. R. S. Dias, M. B. Santos, S. de Albuquerque, H. C. Castro, A. M. T. de Souza, A. C. C. Freitas, M. A. V. DiVaio, L. M. Cabral, and C. R. Rodrigues, Bioorg. Med. Chem., 15, 211 (2007).
C. Liu, Z. Li, L. Zhao, and L. Shen, ARKIVOC, ii, 258 (2009).
S. Lee and S. B. Park, Org. Lett., 11, 5214 ( 2009).
X. Fan, X. Wang, X. Zhang, X. Li, and G. Qu, Heteroatom Chem., 19, 694 (2008).
D.-Q. Shi, J.-W. Shi, H. Yao, H. Jiang, and X.-S. Wang, J. Chin. Chem. Soc., 54, 1341 (2007).
J. Häufel and E. Breitmaier, Angew. Chem., 85, 959 (1973).
J. Häufel and E. Breitmaier, Angew. Chem., 86, 671 (1974).
A. Kumari, Thesis M. Sc., Rourkela, 2009.
J. Bartulin, J. Belmar, and G. Leon, Bol. Soc. Chil. Quím., 37, 13 (1992).
E. J. Barreiro, C. A. Camara, H. Verli, L. Brazil-Más, N. G. Castro, W. M. Cintra, Y. Aracava, C. R. Rodrigues, and C. A. M. Fraga, J. Med. Chem., 46, 1144 (2003).
C.-C. Cheng, S.-Y. Yan, in: W. C. Dauben (editor), Organic Reactions, J. Wiley & Sons, New York, 1982, Vol. 28, p. 37.
P. Mundy and M. G. Ellerd, Name Reactions and Reagents in Organic Synthesis, J. Wiley & Sons, New York, 1988, p. 86.
A. Hassner and C. Stumer, in: P. D. Magnus (editor), Organic Synthesis Based on Named and Unnamed Reactions (Tetrahedron Organic Chemistry Series), J. E. Baldwin, Elsevier Sci., Oxford, New York, Tokyo, 1994, Vol. 11, p. 132.
G. Karthikeyan and P. T. Perumal, J. Heterocyclic Chem., 41, 1039 (2004).
V. K. Ahluwalia and B. Goyal, Synth. Commun., 26, 1341 (1996).
V. K. Ahluwalia and A. Dahiya, Indian J. Chem., 35B, 1208 (1996).
V. K. Ahluwalia, A. Dahiya, and V. K. Garg, Indian J. Chem., 36B, 88 (1997).
T. I. El-Emary, J. Chin. Chem. Soc., 46, 585 (1999).
M. Hussein and T. I. El-Emary, J. Chem. Res. (S), 20 (1998).
A. Zheng, W. Zhang, and J. Pan, Synth. Commun., 36, 1549 (2006).
T. Premkumar and S. Govindarajan, World J. Microbiol. Biotechnol., 21, 479 (2005).
Cremer, Antibiotic Sensitivity and Assay Tests, Butterworth, London, 4th ed., 1980, p. 521.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1857–1866, December, 2010.
Rights and permissions
About this article
Cite this article
Panda, N., Karmakar, S. & Jena, A.K. Synthesis and antibacterial activity of some novel pyrazolopyridine derivatives. Chem Heterocycl Comp 46, 1500–1508 (2011). https://doi.org/10.1007/s10593-011-0699-y
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-011-0699-y