Main Article Content
Abstract
A new series of 2-[1-(1,3-diphenyl-1H-pyrazol-4-yl)-meth-(E)-ylidene]-indan-1-one derivatives (5a-l) have been synthesized through through the Knoevenagel condensation of pyrazole carbaldehydes with differently substituted 1-indanone derivatives in the presence of base. A high yielding and solvent-free method was developed for the synthesis of hydrazones from acetophenones under microwave irradiation in a very short reaction time. Structures of the newly synthesized compounds were affirmed by IR, 1H & 13C NMR and mass spectroscopic analysis. The confirmed structures were screened for their antibacterial potency against S. aureus and E. coli bacterial strains. Among the series, compounds 5b, 5c and 5f were evoked as potent antibacterial agents.
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References
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- M.V. Vita, P. Caramenti and J. Waser, Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation, Org. Lett., 17, 5832 (2015); https://doi.org/10.1021/acs.orglett.5b03002
- S.K. Mandal, Indanyl Analogs as Potential Antimicrobial Agents, Asian J. Pharm. Clin. Res., 11, 278 (2018); https://doi.org/10.22159/ajpcr.2018.v11i5.24635
- A.F. Olatomide, A.A. David, E. Henry and A.O. Craig, 1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone Derivatives: Synthesis, Physicochemical Properties and in vitro Antibacterial Activity, African J. Pure Appl. Chem., 8, 68 (2014); https://doi.org/10.5897/AJPAC2014.0558
- M.C. Soraires Santacruz, M. Fabiani, E.F. Castro, L.V. Cavallaro and L.M. Finkielsztein, Synthesis, Antiviral Evaluation and Molecular Docking Studies of N4-Aryl Substituted/Unsubstituted Thiosemicarbazones Derived from 1-indanones as Potent Anti-bovine Viral Diarrhea Virus Agents, Bioorg. Med. Chem., 25, 4055 (2017); https://doi.org/10.1016/j.bmc.2017.05.056
- H.O. Saxena, U. Faridi, S. Srivastava, J.K. Kumar, M.P. Darokar, S. Luqman, C.S. Chanotiya, V. Krishna, A.S. Negi and S.P.S. Khanuja, Gallic Acid-Based Indanone Derivatives as Anticancer Agents, Bioorg. Med. Chem. Lett., 18, 3914 (2008); https://doi.org/10.1016/j.bmcl.2008.06.039
- M.S.M. Sabri, W.C. Oo and M.F. Yam, Synthesis, Characterization and Vasolidation Properties of Indanone-Based Chalcones, J. Physiol. Sci., 29(Suppl.1), 99 (2018); https://doi.org/10.21315/jps2018.29.s1.13
- N. Siddiqui, M.F. Arshad, S.A. Khan, W. Ahsan, R. Ali, M. Shamsher Alam and S. Ahmed, Synthesis of New Piperidyl Indanone Derivatives as Anticonvulsant Agents, Med. Chem. Res., 21, 726 (2012); https://doi.org/10.1007/s00044-011-9584-6
- C.-Y. Chen, F.-Y. Chiu, Y. Lin, W.-J. Huang, P.-S. Hsieh and F.-L. Hsu, Chemical Constituents Analysis and Antidiabetic Activity Validation of Four Fern Species from Taiwan, Int. J. Mol. Sci., 16, 2497 (2015); https://doi.org/10.3390/ijms16022497
- C.J.M.D.S. Menezes, Arylidene Indanone Scaffold: Medicinal Chemistry and Structure-Activity Relationship View, RSC Adv., 7, 9357 (2017); https://doi.org/10.1039/C6RA28613E
- I. Bottcher, A. Schweizer, M. Glatt and H. Werner, A Sulphonamido-Indanone Derivative CGP 28237 (ZK 34228), a Novel Non-Steroidal Anti-Inflammatory Agent without Gastro-Intestinal Ulcerogenicity in Rats, Drugs Exp. Clin. Res., 13, 237 (1987).
- L. Huang, H. Miao, Y. Sun, F. Meng and X. Li, Discovery of Indanone Derivatives as Multi-Target-Directed Ligands against Alzheimer¢s Disease, Eur. J. Med. Chem., 87, 429 (2014); https://doi.org/10.1016/j.ejmech.2014.09.081
- Y. Nakada, S. Ohno, M. Yoshimoto and Y. Yura, Synthesis and Insecticidal Activity of 4-Substituted 1-Indanyl Chrysanthemates, Agric. Biol. Chem., 42, 1365 (1978); https://doi.org/10.1080/00021369.1978.10863166
- S.A. Patil, R. Patil and S.A. Patil, Recent Developments in Biological Activities of Indanones, Eur. J. Med. Chem., 138, 182 (2017); https://doi.org/10.1016/j.ejmech.2017.06.032
- S. Velaparthi, M. Brunsteiner, R. Uddin, B. Wan, S.G. Franzblau and P.A. Petukhov, 5-tert-Butyl-N-pyrazol-4-yl-4,5,6,7-tetrahydrobenzo[d]-isoxazole-3-carboxamide Derivatives as Novel Potent Inhibitors of Mycobacterium tuberculosis Pantothenate Synthetase: Initiating a Quest for New Antitubercular Drugs, J. Med. Chem., 51, 1999 (2008); https://doi.org/10.1021/jm701372r
- G.C. Rovnyak, R.C. Millonig, J. Schwartz and V. Shu, Synthesis and Antiinflammatory Activity of Hexahydrothiopyrano[4,3-c]pyrazoles and Related Analogs, J. Med. Chem., 25, 1482 (1982); https://doi.org/10.1021/jm00354a018
- I.V. Magedov, M. Manpadi, S. Van slambrouck, W.F.A. Steelant, E. Rozhkova, N.M. Przheval’skii, S. Rogelj and A. Kornienko, Discovery and Investigation of Antiproliferative and Apoptosis-Inducing Properties of New Heterocyclic Podophyllotoxin Analogues Accessible by a One-Step Multicomponent Synthesis, J. Med. Chem., 50, 5183 (2007); https://doi.org/10.1021/jm070528f
- G.A. Wachter, R.W. Hartmann, T. Sergejew, G.L. Grun and D. Ledergerber, Tetrahydronaphthalenes: Influence of Heterocyclic Substituents on Inhibition of Steroidogenic Enzymes P450 arom and P450 17, J. Med. Chem., 39, 834 (1996); https://doi.org/10.1021/jm950377t
- F. Colliot, K.A. Kukorowski, D.W. Hawkins and D.A. Roberts, Fipronil: A New Soil and Foliar Broad Spectrum Insecticide,, In: Brighton Crop Protection Conference Pests and Diseases, 1992 Brighton, pp 29-34, November 23-26 (1992).
- H.S. Chen, Z.M. Li and Y.F. Han, Synthesis and Fungicidal Activity against Rhizoctonia solani of 2-Alkyl(alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (Thiadiazoles), J. Agric. Food Chem., 48, 5312 (2000); https://doi.org/10.1021/jf991065s
- C.B. Vicentini, C. Romagnoli, E. Andreotti and D. Mares, Synthetic Pyrazole Derivatives as Growth Inhibitors of Some Phytopathogenic Fungi, J. Agric. Food Chem., 55, 10331 (2007); https://doi.org/10.1021/jf072077d
- C.B. Vicentini, D. Mares, A. Tartari, M. Manfrini and G. Forlani, Synthesis of Pyrazole Derivatives and their Evaluation as Photosynthetic Electron Transport Inhibitors, J. Agric. Food Chem., 52, 1898 (2004); https://doi.org/10.1021/jf035115b
- T.W. Waldrep, J.R. Beck, M.P. Lynch and F.L. Wright, Synthesis and Herbicidal Activity of 1-Aryl-5-halo and 1-Aryl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamides, J. Agric. Food Chem., 38, 541 (1990); https://doi.org/10.1021/jf00092a045
- C.B. Vicentini, S. Guccione, L. Giurato, R. Ciaccio, D. Mares and G. Forlani, Pyrazole Derivatives as Photosynthetic Electron Transport Inhibitors: New Leads and Structure-Activity Relationship, J. Agric. Food Chem., 53, 3848 (2005); https://doi.org/10.1021/jf0500029
- R.D. Clark, Synthesis and QSAR of Herbicidal 3-Pyrazolyl a,a,a-Trifluorotolyl Ethers, J. Agric. Food Chem., 44, 3643 (1996); https://doi.org/10.1021/jf9601978
- B.P. Bandgar, S.A. Patil, J.V. Totre, B.L. Korbad, R.N. Gacche, B.S. Hote, S.S. Jalde and H.V. Chavan, Synthesis and Biological Evaluation of Nitrogen-Containing Benzophenone Analogues as TNF-a and IL-6 Inhibitors with Antioxidant Activity, Bioorg. Med. Chem. Lett., 20, 2292 (2010); https://doi.org/10.1016/j.bmcl.2010.02.001
- B.P. Bandgar, L.K. Adsul, S.V. Lonikar, H.V. Chavan, S.N. Shringare, S.A. Patil, S.S. Jalde, B.A. Koti, N.A. Dhole, R.N. Gacche and A. Shirfule, Synthesis of Novel Carbazole Chalcones as Radical Scavenger, Antimicrobial and Cancer Chemopreventive Agents, J. Enzyme Inhib. Med. Chem., 28, 593 (2013); https://doi.org/10.3109/14756366.2012.663365
- P.S. Bhale, H.V. Chavan, S.B. Dongare, S.N. Shringare, Y.B. Mule, S.S. Nagane and B.P. Bandgar, Synthesis of Extended Conjugated Indolyl Chalcones as Potent Anti-breast Cancer, Anti-inflammatory and Antioxidant Agents, Bioorg. Med. Chem. Lett., 27, 1502 (2017); https://doi.org/10.1016/j.bmcl.2017.02.052
- H.V. Chavan, L.K. Adsul, A.S. Kotmale, V.D. Dhakane, V.N. Thakare and B.P. Bandgar, Design, Synthesis, Characterization and in vitro and in vivo Anti-inflammatory Evaluation of Novel Pyrazole-based Chalcones, J. Enzyme Inhib. Med. Chem., 30, 22 (2015); https://doi.org/10.3109/14756366.2013.873037
References
H. Yu, I.J. Kim, J.E. Folk, X. Tian, R.B. Rothman, M.H. Baumann, C.M. Dersch, J.L. Flippen-Anderson, D. Parrish, A.E. Jacobson and K.C. Rice, Synthesis and Pharmacological Evaluation of 3-(3,4-Dichloro-phenyl)-1-indanamine Derivatives as Nonselective Ligands for Biogenic Amine Transporters, J. Med. Chem., 47, 2624 (2004); https://doi.org/10.1021/jm0305873
M.V. Vita, P. Caramenti and J. Waser, Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation, Org. Lett., 17, 5832 (2015); https://doi.org/10.1021/acs.orglett.5b03002
S.K. Mandal, Indanyl Analogs as Potential Antimicrobial Agents, Asian J. Pharm. Clin. Res., 11, 278 (2018); https://doi.org/10.22159/ajpcr.2018.v11i5.24635
A.F. Olatomide, A.A. David, E. Henry and A.O. Craig, 1-Indanone chalcones and their 2,4-Dinitrophenylhydrazone Derivatives: Synthesis, Physicochemical Properties and in vitro Antibacterial Activity, African J. Pure Appl. Chem., 8, 68 (2014); https://doi.org/10.5897/AJPAC2014.0558
M.C. Soraires Santacruz, M. Fabiani, E.F. Castro, L.V. Cavallaro and L.M. Finkielsztein, Synthesis, Antiviral Evaluation and Molecular Docking Studies of N4-Aryl Substituted/Unsubstituted Thiosemicarbazones Derived from 1-indanones as Potent Anti-bovine Viral Diarrhea Virus Agents, Bioorg. Med. Chem., 25, 4055 (2017); https://doi.org/10.1016/j.bmc.2017.05.056
H.O. Saxena, U. Faridi, S. Srivastava, J.K. Kumar, M.P. Darokar, S. Luqman, C.S. Chanotiya, V. Krishna, A.S. Negi and S.P.S. Khanuja, Gallic Acid-Based Indanone Derivatives as Anticancer Agents, Bioorg. Med. Chem. Lett., 18, 3914 (2008); https://doi.org/10.1016/j.bmcl.2008.06.039
M.S.M. Sabri, W.C. Oo and M.F. Yam, Synthesis, Characterization and Vasolidation Properties of Indanone-Based Chalcones, J. Physiol. Sci., 29(Suppl.1), 99 (2018); https://doi.org/10.21315/jps2018.29.s1.13
N. Siddiqui, M.F. Arshad, S.A. Khan, W. Ahsan, R. Ali, M. Shamsher Alam and S. Ahmed, Synthesis of New Piperidyl Indanone Derivatives as Anticonvulsant Agents, Med. Chem. Res., 21, 726 (2012); https://doi.org/10.1007/s00044-011-9584-6
C.-Y. Chen, F.-Y. Chiu, Y. Lin, W.-J. Huang, P.-S. Hsieh and F.-L. Hsu, Chemical Constituents Analysis and Antidiabetic Activity Validation of Four Fern Species from Taiwan, Int. J. Mol. Sci., 16, 2497 (2015); https://doi.org/10.3390/ijms16022497
C.J.M.D.S. Menezes, Arylidene Indanone Scaffold: Medicinal Chemistry and Structure-Activity Relationship View, RSC Adv., 7, 9357 (2017); https://doi.org/10.1039/C6RA28613E
I. Bottcher, A. Schweizer, M. Glatt and H. Werner, A Sulphonamido-Indanone Derivative CGP 28237 (ZK 34228), a Novel Non-Steroidal Anti-Inflammatory Agent without Gastro-Intestinal Ulcerogenicity in Rats, Drugs Exp. Clin. Res., 13, 237 (1987).
L. Huang, H. Miao, Y. Sun, F. Meng and X. Li, Discovery of Indanone Derivatives as Multi-Target-Directed Ligands against Alzheimer¢s Disease, Eur. J. Med. Chem., 87, 429 (2014); https://doi.org/10.1016/j.ejmech.2014.09.081
Y. Nakada, S. Ohno, M. Yoshimoto and Y. Yura, Synthesis and Insecticidal Activity of 4-Substituted 1-Indanyl Chrysanthemates, Agric. Biol. Chem., 42, 1365 (1978); https://doi.org/10.1080/00021369.1978.10863166
S.A. Patil, R. Patil and S.A. Patil, Recent Developments in Biological Activities of Indanones, Eur. J. Med. Chem., 138, 182 (2017); https://doi.org/10.1016/j.ejmech.2017.06.032
S. Velaparthi, M. Brunsteiner, R. Uddin, B. Wan, S.G. Franzblau and P.A. Petukhov, 5-tert-Butyl-N-pyrazol-4-yl-4,5,6,7-tetrahydrobenzo[d]-isoxazole-3-carboxamide Derivatives as Novel Potent Inhibitors of Mycobacterium tuberculosis Pantothenate Synthetase: Initiating a Quest for New Antitubercular Drugs, J. Med. Chem., 51, 1999 (2008); https://doi.org/10.1021/jm701372r
G.C. Rovnyak, R.C. Millonig, J. Schwartz and V. Shu, Synthesis and Antiinflammatory Activity of Hexahydrothiopyrano[4,3-c]pyrazoles and Related Analogs, J. Med. Chem., 25, 1482 (1982); https://doi.org/10.1021/jm00354a018
I.V. Magedov, M. Manpadi, S. Van slambrouck, W.F.A. Steelant, E. Rozhkova, N.M. Przheval’skii, S. Rogelj and A. Kornienko, Discovery and Investigation of Antiproliferative and Apoptosis-Inducing Properties of New Heterocyclic Podophyllotoxin Analogues Accessible by a One-Step Multicomponent Synthesis, J. Med. Chem., 50, 5183 (2007); https://doi.org/10.1021/jm070528f
G.A. Wachter, R.W. Hartmann, T. Sergejew, G.L. Grun and D. Ledergerber, Tetrahydronaphthalenes: Influence of Heterocyclic Substituents on Inhibition of Steroidogenic Enzymes P450 arom and P450 17, J. Med. Chem., 39, 834 (1996); https://doi.org/10.1021/jm950377t
F. Colliot, K.A. Kukorowski, D.W. Hawkins and D.A. Roberts, Fipronil: A New Soil and Foliar Broad Spectrum Insecticide,, In: Brighton Crop Protection Conference Pests and Diseases, 1992 Brighton, pp 29-34, November 23-26 (1992).
H.S. Chen, Z.M. Li and Y.F. Han, Synthesis and Fungicidal Activity against Rhizoctonia solani of 2-Alkyl(alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles (Thiadiazoles), J. Agric. Food Chem., 48, 5312 (2000); https://doi.org/10.1021/jf991065s
C.B. Vicentini, C. Romagnoli, E. Andreotti and D. Mares, Synthetic Pyrazole Derivatives as Growth Inhibitors of Some Phytopathogenic Fungi, J. Agric. Food Chem., 55, 10331 (2007); https://doi.org/10.1021/jf072077d
C.B. Vicentini, D. Mares, A. Tartari, M. Manfrini and G. Forlani, Synthesis of Pyrazole Derivatives and their Evaluation as Photosynthetic Electron Transport Inhibitors, J. Agric. Food Chem., 52, 1898 (2004); https://doi.org/10.1021/jf035115b
T.W. Waldrep, J.R. Beck, M.P. Lynch and F.L. Wright, Synthesis and Herbicidal Activity of 1-Aryl-5-halo and 1-Aryl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamides, J. Agric. Food Chem., 38, 541 (1990); https://doi.org/10.1021/jf00092a045
C.B. Vicentini, S. Guccione, L. Giurato, R. Ciaccio, D. Mares and G. Forlani, Pyrazole Derivatives as Photosynthetic Electron Transport Inhibitors: New Leads and Structure-Activity Relationship, J. Agric. Food Chem., 53, 3848 (2005); https://doi.org/10.1021/jf0500029
R.D. Clark, Synthesis and QSAR of Herbicidal 3-Pyrazolyl a,a,a-Trifluorotolyl Ethers, J. Agric. Food Chem., 44, 3643 (1996); https://doi.org/10.1021/jf9601978
B.P. Bandgar, S.A. Patil, J.V. Totre, B.L. Korbad, R.N. Gacche, B.S. Hote, S.S. Jalde and H.V. Chavan, Synthesis and Biological Evaluation of Nitrogen-Containing Benzophenone Analogues as TNF-a and IL-6 Inhibitors with Antioxidant Activity, Bioorg. Med. Chem. Lett., 20, 2292 (2010); https://doi.org/10.1016/j.bmcl.2010.02.001
B.P. Bandgar, L.K. Adsul, S.V. Lonikar, H.V. Chavan, S.N. Shringare, S.A. Patil, S.S. Jalde, B.A. Koti, N.A. Dhole, R.N. Gacche and A. Shirfule, Synthesis of Novel Carbazole Chalcones as Radical Scavenger, Antimicrobial and Cancer Chemopreventive Agents, J. Enzyme Inhib. Med. Chem., 28, 593 (2013); https://doi.org/10.3109/14756366.2012.663365
P.S. Bhale, H.V. Chavan, S.B. Dongare, S.N. Shringare, Y.B. Mule, S.S. Nagane and B.P. Bandgar, Synthesis of Extended Conjugated Indolyl Chalcones as Potent Anti-breast Cancer, Anti-inflammatory and Antioxidant Agents, Bioorg. Med. Chem. Lett., 27, 1502 (2017); https://doi.org/10.1016/j.bmcl.2017.02.052
H.V. Chavan, L.K. Adsul, A.S. Kotmale, V.D. Dhakane, V.N. Thakare and B.P. Bandgar, Design, Synthesis, Characterization and in vitro and in vivo Anti-inflammatory Evaluation of Novel Pyrazole-based Chalcones, J. Enzyme Inhib. Med. Chem., 30, 22 (2015); https://doi.org/10.3109/14756366.2013.873037