Abstract
We present a novel, facile and efficient methodology for the synthesis of pyrazoles and pyrazolo[3,4-d]pyridazines linked to diaryl sulfone moiety using synthetic talc as a solid base catalyst under microwave irradiation, via 1,3-dipolar cycloaddition reaction of the E-3-(dimethylamino)-1-(4-(phenylsulfonyl)phenyl)prop-2-en-1-one with different hydrazonyl halides. All synthesized compounds were evaluated for antibacterial and antifungal activities. The results showed that most of the synthesized compounds exhibited promising antimicrobial activities.
Similar content being viewed by others
References
P. Prasit, Z. Wang, C. Brideau, C.C. Chan, S. Charleson, W. Cromlish, D. Ethier, J.F. Evans, A.W. Ford-Hutchinson, J.Y. Gauthier, R. Gordon, J. Guay, M. Gresser, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J. Mancini, G.P. O’Neill, M. Ouellet, M.D. Percival, H. Perrier, D. Riendeau, I. Rodger, P. Tagari, M. Therien, P. Vickers, E. Wong, L.J. Xu, R.N. Young, R. Zamboni, S. Boyce, N. Rupniak, N. Forrest, D. Visco, D. Patrick, Bioorg. Med. Chem. Lett. 9, 1773 (1999)
R. Wolf, H. Matz, E. Orion, B. Tuzun, Y. Tuzun, Dapsone. Dermatol. Online J. 8, 2 (2002)
G.H. Faget, R.C. Pogge, F.A. Johansen, J.F. Dinan, B.M. Prejean, C.G. Eccles, Int. J. Lepr. Other Mycobact. Dis. 34, 298 (1966)
S.F. Barbuceanu, D.C. Ilies, G. Saramet, V. Uivarosi, C. Draghici, V. Radulescu, Int. J. Mol. Sci. 15, 10908 (2014)
S.F. Barbuceanu, G.L. Almajan, I. Saramet, C. Draghici, R. Socoteanu, F. Barbuceanu, G. Bancescu, J. Serb. Chem. Soc. 74, 1041 (2009)
S.F. Barbuceanu, G.L. Almajan, I. Saramet, C. Draghici, A.I. Tarcomnicu, G. Bancescu, Eur. J. Med. Chem. 44, 4752 (2009)
G.L. Almajan, S.F. Barbuceanu, E.R. Almajan, C. Draghici, G. Saramet, Eur. J. Med. Chem. 44, 3083 (2009)
G.L. Almajan, S.F. Barbuceanu, A. Innocenti, A. Scozzafava, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 23, 101 (2008)
S.F. Barbuceanu, G. Saramet, G.L. Almajan, C. Draghici, F. Barbuceanu, G. Bancescu, Eur. J. Med. Chem. 49, 417 (2012)
T.J. Sultivan, J.J. Truglio, M.E. Boyne, P. Novichenok, X. Zhang, C.F. Stratton, H.J. Li, T. Kaur, A. Amin, F. Johnson, R.A. Stayden, C. Kisker, P.J. Tonge, ACS Chem. Biol. 1, 43 (2006)
X.H. Liu, P. Cui, B.A. Song, P.S. Bhadury, H.L. Zhu, S.F. Wang, Bioorg. Med. Chem. 16, 4075 (2008)
H. Foks, D. Pancechowska-Ksepko, A. Kedzia, Z. Zwolska, M. Janowiec, E. Augustynowicz-Kopec, II Farmaco 60, 513 (2005)
A.M. Gilbert, A. Failli, J. Shumsky, Y. Yang, A. Severin, G. Singh, W. Hu, D. Keeney, P.J. Petersen, A.H. Katz, J. Med. Chem. 49, 6027 (2006)
A.H. Shamroukh, M.E.A. Zaki, E.M.H. Morsy, F.M. Abdel-Motti, F.M.E. Abdel-Megeid, Arch. Pharm. Chem. Life Sci. 340, 345 (2007)
O. Prakash, R. Kumar, V. Parkash, Eur. J. Med. Chem. 43, 435 (2008)
O. Prakash, R. Pundeer, P. Ranjan, K. Pannu, Y. Dhingra, K.R. Aneja, Indian J. Chem. 48B, 563 (2009)
R. Storer, C.J. Ashton, A.D. Baxter, M.M. Hann, C.L.P. Marr, A.M. Mason, P.L. Myers, S.A. Noble, H.R. Penn, N.G. Weir, G. Niall, J.M. Woods, P.L. Coe, Nucleotides 18, 203 (1999)
M.J. Genin, C. Biles, B.J. Keiser, S.M. Poppe, S.M. Swaney, W.G. Tarpley, Y. Yagi, D.L. Romero, J. Med. Chem. 43, 1034 (2000)
G. Daidone, B. Maggio, S. Plescia, D. Raffa, C. Musiu, C. Milia, G. Perra, M.E. Marongiu, Eur. J. Med. Chem. 33, 375 (1998)
S.A. Gamage, J.A. Spicer, G.W. Rewcastle, J. Milton, S. Sohal, W. Dangerfield, P. Mistry, N. Vicker, P.A. Charlton, W.A. Denny, J. Med. Chem. 45, 740 (2002)
G.W.V. Cave, C.L. Raston, J.L. Scott, Chem. Commun. 21, 2159 (2001). doi:10.1039/B106677n
V. Polshettiwar, R.S. Varma, Acc. Chem. Res. 41, 629 (2008)
A. Stolle, T. Szuppa, S.E.S. Leonhardt, B. Ondruschka, Chem. Soc. Rev. 40, 2317 (2011)
R.K. Rawal, Y.S. Phabhakar, S.B. Kati, E. De Clercq, Bioorg. Med. Chem. 13, 6771 (2005)
C.G. Bonde, N.J. Gaikwad, Bioorg. Med. Chem. 12, 2151 (2004)
R.K. Rawal, R. Tripathi, S.B. Kati, C. Pannecouque, E. De Clercq, Bioorg. Med. Chem. 15, 1725 (2007)
P.P. Dixit, V.J. Patil, P.S. Nair, S. Jain, N. Sinha, S.K. Arora, Eur. J. Med. Chem. 41, 423 (2006)
Z.A. Kaplancikli, G. Turan-Zitouni, A. Özdemir, G. Revial, Eur. J. Med. Chem. 43, 155 (2008)
M.F. Mady, G.E.A. Awad, K.B. Jorgensen, Eur. J. Med. Chem. 84, 433 (2014)
N.M.A. El-Rahman, T.S. Saleh, M.F. Mady, Ultrason. Sonochem. 16, 70 (2009)
A.A. El-Kateb, N.M. Abd El-Rahman, T.S. Saleh, I.F. Zeid, M.F. Mady, Life Sci. J. 9, 711 (2012)
N.M.A. Ei-Rahman, A.A. Ei-Kateb, M.F. Mady, Synth. Commun. 37, 3961 (2007)
L. Pedersen, M.F. Mady, M.O. Sydnes, Tetrahedron Lett. 54, 4772 (2013)
B. Stanovnik, J. Svete, Chem. Rev. 104, 2433 (2004)
R. Jakse, J. Svete, B. Stanovnik, A. Golohie, Tetrahedron 60, 4601 (2004)
E. Bejan, H.A. Haddou, J.E. Daran, G.G.A. Balavoine, Synthesis 8, 1012 (1996)
M.R. Shaaban, T.S. Saleh, A.M. Farag, Heterocycles 78, 151 (2009)
M.R. Shaaban, T.S. Saleh, A.M. Farag, Heterocycles 78, 699 (2009)
M.R. Shaaban, T.S. Saleh, F.H. Osman, A.M. Farag, J. Heterocycl. Chem. 44, 177 (2007)
T.S. Saleh, M.A. Al-Omar, H.A. Abdel-Aziz, Lett. Org. Chem. 7, 483 (2010)
H.A. Patel, S.K. Sharma, R.V. Jasra, J. Mol. Catal. A Chem. 286, 31 (2008)
D. Sgouras, P. Maragkoudakis, K. Petraki, B. Martinez-Gonzalez, E. Eriotou, S. Michopoulos, G. Kalantzopoulos, E. Tsakalidou, A. Mentis, Appl. Environ. Microbiol. 70, 518 (2004)
C. Wiart, Oxford J. Med. 4, 299 (2007)
J.M. Andrews, J. Antimicrob. Chemother. 48, 5 (2001)
J. Zou, F. Li, F.G. Tao, Chin. Chem. Lett. 20, 17 (2009)
A.M. Farag, M.S. Algharib, Org. Prep and Proced. Int. 20, 521 (1988)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mady, M.F., Saleh, T.S., El-Kateb, A.A. et al. Microwave-assisted synthesis of novel pyrazole and pyrazolo[3,4-d]pyridazine derivatives incorporating diaryl sulfone moiety as potential antimicrobial agents. Res Chem Intermed 42, 753–769 (2016). https://doi.org/10.1007/s11164-015-2054-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2054-x