Copyright (c) 2025 Ajay Ambhore
This work is licensed under a Creative Commons Attribution 4.0 International License.
Pyrazole-Embedded Pyridazine and Phthalazinedione Hybrids: Synthesis, Characterization and Anti-Inflammatory Potential
Corresponding Author(s) : Ajay N. Ambhore
Asian Journal of Chemistry,
Vol. 37 No. 10 (2025): Vol 37 Issue 10, 2025
Abstract
The synthesis of heterocycles incorporating bridgehead nitrogen, particularly pyridazine and phthalazinedione derivatives, has garnered significant interest due to their wide-ranging applications in various pharmacological fields. Recognizing the importance of eco-friendly protocols, this work reports a novel green synthetic route for the preparation of pyridazine and phthalazinedione derivatives featuring a pyrazole moiety. In this synthetic route, a one-pot multi-component reaction was performed using 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (1), various substituted aldehydes (2), hydrazine hydrate (3) and different anhydrides (4–6). The synthesized compounds were characterized and screened for their anti-inflammatory activity. Most of the compounds showed good anti-inflammatory activity.
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- M. Tandi, V. Sharma, B. Gopal and S. Sundriyal, RSC Adv., 15, 1447 (2025); https://doi.org/10.1039/D4RA06681B
- S.E. John, S. Gulatia and N. Shankaraiah, Org. Chem. Front., 8, 4237 (2021); https://doi.org/10.1039/D0QO01480J
- L.A. Thompson, Curr. Opin. Chem. Biol., 4, 324 (2000); https://doi.org/10.1016/S1367-5931(00)00096-X
- A. Domling, Curr. Opin. Chem. Biol., 6, 306 (2002); https://doi.org/10.1016/S1367-5931(02)00328-9
- X.L. Sun, J.C. Zheng and Y. Tang, Pure Appl. Chem., 82, 625 (2010); https://doi.org/10.1351/PAC-CON-09-10-20
- H.R. Shaterian and M. Mohammadnia, J. Mol. Liq., 173, 55 (2012); https://doi.org/10.1016/j.molliq.2012.06.007
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- A.M. Buysse, M.C.H. Yap, R. Hunter, J. Babcock and X. Huang, Pest Manag. Sci., 73, 782 (2017); https://doi.org/10.1002/ps.4465
- H. Cerecetto, A. Gerpe, M. González, V. J. Arán, and C. Ochoa de Ocáriz, Mini-Rev. Med. Chem., 5, 869 (2005); https://doi.org/10.2174/138955705774329564
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- W. Han, J.C. Pelletier and C.N. Hodge, Bioorg. Med. Chem. Lett., 8, 3615 (1998); https://doi.org/10.1016/S0960-894X(98)00659-3
- H.D.H. Showalter, M.M. Angelo, E. Berman, G.D. Kanter, D.F. Ortwine, S.G. Ross-Kesten, A.D. Sercel, W.R. Turner, L.M. Werbel, D.F. Worth, E.F. Elslager, W.R. Leopald and J.L. Shillis, J. Med. Chem., 31, 1527 (1988); https://doi.org/10.1021/jm00403a009
- L. Nagarapu, R. Bantu and H.B. Mereyala, J. Heterocycl. Chem., 46, 728 (2009); https://doi.org/10.1002/jhet.135
- A. Hasaninejed, M.R. Kazerooni and A. Zare, Catal. Today, 196, 148 (2012); https://doi.org/10.1016/j.cattod.2012.05.026
- M. Kidwai, A. Jahan, R. Chauhan, N. Mishra and K. Neeraj, Tetrahedron Lett., 53, 1728 (2012); https://doi.org/10.1016/j.tetlet.2012.01.095
- H.R. Shaterian, F. Khorami, A. Amirzadeh, R. Doostmohammadi and M. Ghashang, J. Iran. Chem. Res., 2, 57 (2009).
- E. Mosaddegh and A. Hassankhani, Tetrahedron Lett., 52, 488 (2011); https://doi.org/10.1016/j.tetlet.2010.08.099
- R. Fazaeli, H. Aliyan and N. Fazaeli, Open Catal. J., 3, 14 (2010); https://doi.org/10.2174/1876214X01003010014
- B. Pouramiri and E.T. Kermani, Tetrahedron Lett., 57, 1006 (2016); https://doi.org/10.1016/j.tetlet.2016.01.074
- H.R. Shaterian, A. Hosseinian and M. Ghashang, ARKIVOC, 2, 59 (2009); https://doi.org/10.3998/ark.5550190.0010.207
References
M. Tandi, V. Sharma, B. Gopal and S. Sundriyal, RSC Adv., 15, 1447 (2025); https://doi.org/10.1039/D4RA06681B
S.E. John, S. Gulatia and N. Shankaraiah, Org. Chem. Front., 8, 4237 (2021); https://doi.org/10.1039/D0QO01480J
L.A. Thompson, Curr. Opin. Chem. Biol., 4, 324 (2000); https://doi.org/10.1016/S1367-5931(00)00096-X
A. Domling, Curr. Opin. Chem. Biol., 6, 306 (2002); https://doi.org/10.1016/S1367-5931(02)00328-9
X.L. Sun, J.C. Zheng and Y. Tang, Pure Appl. Chem., 82, 625 (2010); https://doi.org/10.1351/PAC-CON-09-10-20
H.R. Shaterian and M. Mohammadnia, J. Mol. Liq., 173, 55 (2012); https://doi.org/10.1016/j.molliq.2012.06.007
H.R. Shaterian and K. Azizi, J. Mol. Liq., 183, 8 (2013); https://doi.org/10.1016/j.molliq.2013.04.005
A.M. Buysse, M.C.H. Yap, R. Hunter, J. Babcock and X. Huang, Pest Manag. Sci., 73, 782 (2017); https://doi.org/10.1002/ps.4465
H. Cerecetto, A. Gerpe, M. González, V. J. Arán, and C. Ochoa de Ocáriz, Mini-Rev. Med. Chem., 5, 869 (2005); https://doi.org/10.2174/138955705774329564
M. De Angelis, F. Stossi, K.A. Carlson, B.S. Katzenellenbogen and J.A. Katzenellenbogen, J. Med. Chem., 48, 1132 (2005); https://doi.org/10.1021/jm049223g
H.C. Zhang, C.K. Derian, D.F. McComsey, K.B. White, H. Ye, L.R. Hecker, J. Li, M.F. Addo, D. Croll, J. Eckardt, C.E. Smith, Q. Li, W.M. Cheung, B.R. Conway, S. Emanuel, K.T. Demarest, P. Andrade-Gordon, B.P. Damiano and B.E. Maryanoff, J. Med. Chem., 48, 1725 (2005); https://doi.org/10.1021/jm049478u
J.A. May, A.P. Dantanarayana, P.W. Zinke, M.A. McLaughlin and N.A. Sharif, J. Med. Chem., 49, 318 (2006); https://doi.org/10.1021/jm050663x
W. Han, J.C. Pelletier and C.N. Hodge, Bioorg. Med. Chem. Lett., 8, 3615 (1998); https://doi.org/10.1016/S0960-894X(98)00659-3
H.D.H. Showalter, M.M. Angelo, E. Berman, G.D. Kanter, D.F. Ortwine, S.G. Ross-Kesten, A.D. Sercel, W.R. Turner, L.M. Werbel, D.F. Worth, E.F. Elslager, W.R. Leopald and J.L. Shillis, J. Med. Chem., 31, 1527 (1988); https://doi.org/10.1021/jm00403a009
L. Nagarapu, R. Bantu and H.B. Mereyala, J. Heterocycl. Chem., 46, 728 (2009); https://doi.org/10.1002/jhet.135
A. Hasaninejed, M.R. Kazerooni and A. Zare, Catal. Today, 196, 148 (2012); https://doi.org/10.1016/j.cattod.2012.05.026
M. Kidwai, A. Jahan, R. Chauhan, N. Mishra and K. Neeraj, Tetrahedron Lett., 53, 1728 (2012); https://doi.org/10.1016/j.tetlet.2012.01.095
H.R. Shaterian, F. Khorami, A. Amirzadeh, R. Doostmohammadi and M. Ghashang, J. Iran. Chem. Res., 2, 57 (2009).
E. Mosaddegh and A. Hassankhani, Tetrahedron Lett., 52, 488 (2011); https://doi.org/10.1016/j.tetlet.2010.08.099
R. Fazaeli, H. Aliyan and N. Fazaeli, Open Catal. J., 3, 14 (2010); https://doi.org/10.2174/1876214X01003010014
B. Pouramiri and E.T. Kermani, Tetrahedron Lett., 57, 1006 (2016); https://doi.org/10.1016/j.tetlet.2016.01.074
H.R. Shaterian, A. Hosseinian and M. Ghashang, ARKIVOC, 2, 59 (2009); https://doi.org/10.3998/ark.5550190.0010.207
