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One-Pot Green Synthesis of Pyridine-2-carbaldehyde based Chalcones under Solvent-Free Condition using Mesoporous MCM-41 Materials and their Antimicrobial Activities
Corresponding Author(s) : Jayarangarao Prathipati
Asian Journal of Chemistry,
Vol. 34 No. 6 (2022): Vol 34 Issue 6
Abstract
A simplistic one-pot synthetic protocol was performed using aromatic ketones (1a-e) and substituted pyridine-2-carbaldehydes (2a-e) to obtain various substituted chalcones (3a-e). The synthesis was catalyzed by various metal incorporated (Mn, Al) and acid functionalized (H2SO4, H3PW12O40) mesoporous MCM-41 materials, under solvent free conditions. Using pyridine-2-carbaldehyde (2a), its analogs viz., 4-methoxy (2b), 4-chloro (2c), 4-hydroxy (2d) and 4-nitro (2e) pyridine-2-carbaldehydes were synthesized separately, in order to use these precursors for the formation of the organic derivatives 3b to 3e. Their structural features were characterized by using 1H NMR, 13C NMR and mass spectral techniques. Both the acid functionalized MCM-41 were almost equal in their catalytic performance, whereas among the Mn+-MCM-41 [Mn+ = Mn/Al], the Al incorporated material has shown slightly higher catalytic performance. The antimicrobial activities of the derivatives (3a-e), was investigated on the selected microorganisms, using standard procedures. In these studies, except the compound 3e, remaining compounds have displayed superior biological activity.
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- B. Salehi, C. Quispe, I. Chamkhi, N. El-Omari, A. Balahbib, J. SharifiRad. A. Bouyahya, M. Akram, M. Iqbal, A.O. Docea, C. Caruntu, G. Leyva-Gómez, A. Dey, M. Martorell, D. Calina, V. López and F. Les, Front. Pharmacol., 11, 592654 (2021); https://doi.org/10.3389/fphar.2020.592654
- K. Lahtchev, D. Batovska, S.P. Parushev, V.M. Ubiyvovk and A.A. Sibirny, Eur. J. Med. Chem., 43, 2220 (2008); https://doi.org/10.1016/j.ejmech.2007.12.027
- M. Liu, P. Wilairat, S.L. Croft, A.L.-C. Tan and M.-L. Go, Bioorg. Med. Chem., 11, 2729 (2003); https://doi.org/10.1016/S0968-0896(03)00233-5
- X. Wu, P. Wilairat and M.-L. Go, Bioorg. Med. Chem. Lett., 12, 2299 (2002); https://doi.org/10.1016/S0960-894X(02)00430-4
- K. Kyogoku, K. Hatayama, S. Yokomori, R. Saziki, S. Nakane, M. Sasajima, J. Sawada, M. Ohzeki and I. Tanaka, Chem. Pharm. Bull. (Tokyo), 27, 2943 (1979); https://doi.org/10.1248/cpb.27.2943
- J.-Z. Wu, C.-C. Cheng, L.-L. Shen, Z.-K. Wang, S.-B. Wu, W.-L. Li, S.-H. Chen, R.-P. Zhou and P.-H. Qiu, Int. J. Mol. Sci., 15, 18525 (2014); https://doi.org/10.3390/ijms151018525
- S.A. Lahsasni, F.H. Al Korbi and N.A.-A. Aljaber, Chem. Cent. J., 8, 32 (2014); https://doi.org/10.1186/1752-153X-8-32
- Z.-H. Chen, C.-J. Zheng, L.-P. Sun and H.-R. Piao, Eur. J. Med. Chem., 45, 5739 (2010); https://doi.org/10.1016/j.ejmech.2010.09.031
- S.A. Khan, A.M. Asiri, S. Kumar and K. Sharma, Eur. J. Chem., 5, 85 (2014); https://doi.org/10.5155/eurjchem.5.1.85-90.789
- B. Wegiel, Y. Wang, M. Li, F. Jernigan and L. Sun, Cell Cycle, 15, 1288 (2016); https://doi.org/10.1080/15384101.2016.1160980
- S. Syam, S.I. Abdelwahab, M.A. Al-Mamary and S. Mohan, Molecules, 17, 6179 (2012); https://doi.org/10.3390/molecules17066179
- T. Enoki, H. Ohnogi, K. Nagamine, Y. Kudo, K. Sugiyama, M. Tanabe, E. Kobayashi, H. Sagawa and I. Kato, J. Agric. Food Chem., 55, 6013 (2007); https://doi.org/10.1021/jf070720q
- C.-T. Hsieh, T.-J. Hsieh, M. El-Shazly, D.-W. Chuang, Y.-H. Tsai, C.- T. Yen, S.-F. Wu, Y.-C. Wu and F.-R. Chang, Bioorg. Med. Chem. Lett., 22, 3912 (2012); https://doi.org/10.1016/j.bmcl.2012.04.108
- M. Gomes, E. Muratov, M. Pereira, J. Peixoto, L. Rosseto, P. Cravo, C. Andrade and B. Neves, Molecules, 22, 1210 (2017); https://doi.org/10.3390/molecules22081210
- D.I. Batovska and I.T. Todorova, Curr. Clin. Pharmacol., 5, 1 (2010); https://doi.org/10.2174/157488410790410579
- M.J. Albaladejo, M.J. González-Soria and F. Alonso, Green Chem., 20, 701 (2018); https://doi.org/10.1039/C7GC03436A
- Y. Zhao and Q. Song, Org. Chem. Front., 3, 294 (2016); https://doi.org/10.1039/C5QO00282F
- Y. Masuyama, W. Takamura and N. Suzuki, Eur. J. Org. Chem., 2013, 8033 (2013); https://doi.org/10.1002/ejoc.201301189
- D.A. Engel and G.B. Dudley, Org. Lett., 8, 4027 (2006); https://doi.org/10.1021/ol0616743
- J.S. Yadav, B.V. Subba Reddy and P. Vishnumurthy, Tetrahedron Lett., 49, 4498 (2008); https://doi.org/10.1016/j.tetlet.2008.05.056
- M. Rueping, T. Bootwicha, H. Baars and E. Sugiono, Beilstein J. Org. Chem., 7, 1680 (2011); https://doi.org/10.3762/bjoc.7.198
- R. Mokaya, W. Jones, Z. Luan, M.D. Alba and J. Klinowski, Catal. Lett., 37, 113 (1996); https://doi.org/10.1007/BF00813528
- H. van Bekkum and K.R. Kloetstra, Stud. Surf. Sci. Catal., 117, 171 (1998); https://doi.org/10.1016/S0167-2991(98)80991-9
- A. Corma and D. Kumar, Stud. Surf. Sci. Catal., 117, 201 (1998); https://doi.org/10.1016/S0167-2991(98)80994-4
- I.V. Kozhevnikov, Chem. Rev., 98, 171 (1998); https://doi.org/10.1021/cr960400y
- K. Mohan Reddy, N. Seshu Babu, I. Suryanarayana, P.S. Sai Prasad and N. Lingaiah, Tetrahedron Lett., 47, 7563 (2006); https://doi.org/10.1016/j.tetlet.2006.08.094
- R.R. Nagawade and D.B. Shinde, Acta Chim. Slov., 54, 642 (2007).
- H.X. Pang, Y.H. Hui, K. Fan, X.J. Xing, Y. Wu, J.H. Yang, W. Shi and Z.F. Xie, Chin. Chem. Lett., 27, 335 (2016); https://doi.org/10.1016/j.cclet.2015.10.029
- G.H. Mahdavinia, S. Rostamizadeh, A.M. Amani and H. Sepehrian, Heterocycl. Commun., 18, 33 (2012); https://doi.org/10.1515/hc-2011-0056
- D. Dhar, I. Beadham and S. Chandrasekaran, J. Mol. Catal. A, 142, 361 (1999); https://doi.org/10.1016/S1381-1169(98)00301-X
- D. Dhar, Proc. Indian Acad. Sci. Chem. Sci., 115, 365 (2003); https://doi.org/10.1007/BF02708229
- P.J. Rao and S.P. Douglas, J. Environ. Treat. Techniq., 10, 47 (2022).
- R.S. Daniel and T. Clyde, Antimicrob. Agents Chemother., 7, 15 (1975).
- R. Konuma, K. Umezawa, A. Mizukoshi, K. Kawarada and M. Yoshida, Biotechnol. Lett., 37, 1845 (2015); https://doi.org/10.1007/s10529-015-1870-9
- X. Xu, J. Wu, W. Xu, M. He, M. Fu, L. Chen, A. Zhu and D. Ye, Catal. Today, 281, 527 (2017); https://doi.org/10.1016/j.cattod.2016.03.036
- P. Yadav, M. Yadav, R. Gaur, R. Gupta, G. Arora, P. Rana, A. Srivastava and R.K. Sharma, ChemCatChem, 12, 2488 (2020); https://doi.org/10.1002/cctc.202000148
- A. Solhy, R. Tahir, S. Sebti, R. Skouta, M. Bousmina, M. Zahouily and M. Larzek, Appl. Catal. A Gen., 374, 189 (2010); https://doi.org/10.1016/j.apcata.2009.12.008
- S. Mandge, H.P. Singh, S.D. Gupta, N.S. Hari, Narayana Moorthy, Trends Appl. Sci. Res., 2, 52 (2007); https://doi.org/10.3923/tasr.2007.52.56
- D.R. Palleros, J. Chem. Educ., 81, 1345 (2004); https://doi.org/10.1021/ed081p1345
- S. Eddarir, N. Cotelle, Y. Bakkour and C. Rolando, Tetrahedron Lett., 44, 5359 (2003); https://doi.org/10.1016/S0040-4039(03)01140-7
References
B. Salehi, C. Quispe, I. Chamkhi, N. El-Omari, A. Balahbib, J. SharifiRad. A. Bouyahya, M. Akram, M. Iqbal, A.O. Docea, C. Caruntu, G. Leyva-Gómez, A. Dey, M. Martorell, D. Calina, V. López and F. Les, Front. Pharmacol., 11, 592654 (2021); https://doi.org/10.3389/fphar.2020.592654
K. Lahtchev, D. Batovska, S.P. Parushev, V.M. Ubiyvovk and A.A. Sibirny, Eur. J. Med. Chem., 43, 2220 (2008); https://doi.org/10.1016/j.ejmech.2007.12.027
M. Liu, P. Wilairat, S.L. Croft, A.L.-C. Tan and M.-L. Go, Bioorg. Med. Chem., 11, 2729 (2003); https://doi.org/10.1016/S0968-0896(03)00233-5
X. Wu, P. Wilairat and M.-L. Go, Bioorg. Med. Chem. Lett., 12, 2299 (2002); https://doi.org/10.1016/S0960-894X(02)00430-4
K. Kyogoku, K. Hatayama, S. Yokomori, R. Saziki, S. Nakane, M. Sasajima, J. Sawada, M. Ohzeki and I. Tanaka, Chem. Pharm. Bull. (Tokyo), 27, 2943 (1979); https://doi.org/10.1248/cpb.27.2943
J.-Z. Wu, C.-C. Cheng, L.-L. Shen, Z.-K. Wang, S.-B. Wu, W.-L. Li, S.-H. Chen, R.-P. Zhou and P.-H. Qiu, Int. J. Mol. Sci., 15, 18525 (2014); https://doi.org/10.3390/ijms151018525
S.A. Lahsasni, F.H. Al Korbi and N.A.-A. Aljaber, Chem. Cent. J., 8, 32 (2014); https://doi.org/10.1186/1752-153X-8-32
Z.-H. Chen, C.-J. Zheng, L.-P. Sun and H.-R. Piao, Eur. J. Med. Chem., 45, 5739 (2010); https://doi.org/10.1016/j.ejmech.2010.09.031
S.A. Khan, A.M. Asiri, S. Kumar and K. Sharma, Eur. J. Chem., 5, 85 (2014); https://doi.org/10.5155/eurjchem.5.1.85-90.789
B. Wegiel, Y. Wang, M. Li, F. Jernigan and L. Sun, Cell Cycle, 15, 1288 (2016); https://doi.org/10.1080/15384101.2016.1160980
S. Syam, S.I. Abdelwahab, M.A. Al-Mamary and S. Mohan, Molecules, 17, 6179 (2012); https://doi.org/10.3390/molecules17066179
T. Enoki, H. Ohnogi, K. Nagamine, Y. Kudo, K. Sugiyama, M. Tanabe, E. Kobayashi, H. Sagawa and I. Kato, J. Agric. Food Chem., 55, 6013 (2007); https://doi.org/10.1021/jf070720q
C.-T. Hsieh, T.-J. Hsieh, M. El-Shazly, D.-W. Chuang, Y.-H. Tsai, C.- T. Yen, S.-F. Wu, Y.-C. Wu and F.-R. Chang, Bioorg. Med. Chem. Lett., 22, 3912 (2012); https://doi.org/10.1016/j.bmcl.2012.04.108
M. Gomes, E. Muratov, M. Pereira, J. Peixoto, L. Rosseto, P. Cravo, C. Andrade and B. Neves, Molecules, 22, 1210 (2017); https://doi.org/10.3390/molecules22081210
D.I. Batovska and I.T. Todorova, Curr. Clin. Pharmacol., 5, 1 (2010); https://doi.org/10.2174/157488410790410579
M.J. Albaladejo, M.J. González-Soria and F. Alonso, Green Chem., 20, 701 (2018); https://doi.org/10.1039/C7GC03436A
Y. Zhao and Q. Song, Org. Chem. Front., 3, 294 (2016); https://doi.org/10.1039/C5QO00282F
Y. Masuyama, W. Takamura and N. Suzuki, Eur. J. Org. Chem., 2013, 8033 (2013); https://doi.org/10.1002/ejoc.201301189
D.A. Engel and G.B. Dudley, Org. Lett., 8, 4027 (2006); https://doi.org/10.1021/ol0616743
J.S. Yadav, B.V. Subba Reddy and P. Vishnumurthy, Tetrahedron Lett., 49, 4498 (2008); https://doi.org/10.1016/j.tetlet.2008.05.056
M. Rueping, T. Bootwicha, H. Baars and E. Sugiono, Beilstein J. Org. Chem., 7, 1680 (2011); https://doi.org/10.3762/bjoc.7.198
R. Mokaya, W. Jones, Z. Luan, M.D. Alba and J. Klinowski, Catal. Lett., 37, 113 (1996); https://doi.org/10.1007/BF00813528
H. van Bekkum and K.R. Kloetstra, Stud. Surf. Sci. Catal., 117, 171 (1998); https://doi.org/10.1016/S0167-2991(98)80991-9
A. Corma and D. Kumar, Stud. Surf. Sci. Catal., 117, 201 (1998); https://doi.org/10.1016/S0167-2991(98)80994-4
I.V. Kozhevnikov, Chem. Rev., 98, 171 (1998); https://doi.org/10.1021/cr960400y
K. Mohan Reddy, N. Seshu Babu, I. Suryanarayana, P.S. Sai Prasad and N. Lingaiah, Tetrahedron Lett., 47, 7563 (2006); https://doi.org/10.1016/j.tetlet.2006.08.094
R.R. Nagawade and D.B. Shinde, Acta Chim. Slov., 54, 642 (2007).
H.X. Pang, Y.H. Hui, K. Fan, X.J. Xing, Y. Wu, J.H. Yang, W. Shi and Z.F. Xie, Chin. Chem. Lett., 27, 335 (2016); https://doi.org/10.1016/j.cclet.2015.10.029
G.H. Mahdavinia, S. Rostamizadeh, A.M. Amani and H. Sepehrian, Heterocycl. Commun., 18, 33 (2012); https://doi.org/10.1515/hc-2011-0056
D. Dhar, I. Beadham and S. Chandrasekaran, J. Mol. Catal. A, 142, 361 (1999); https://doi.org/10.1016/S1381-1169(98)00301-X
D. Dhar, Proc. Indian Acad. Sci. Chem. Sci., 115, 365 (2003); https://doi.org/10.1007/BF02708229
P.J. Rao and S.P. Douglas, J. Environ. Treat. Techniq., 10, 47 (2022).
R.S. Daniel and T. Clyde, Antimicrob. Agents Chemother., 7, 15 (1975).
R. Konuma, K. Umezawa, A. Mizukoshi, K. Kawarada and M. Yoshida, Biotechnol. Lett., 37, 1845 (2015); https://doi.org/10.1007/s10529-015-1870-9
X. Xu, J. Wu, W. Xu, M. He, M. Fu, L. Chen, A. Zhu and D. Ye, Catal. Today, 281, 527 (2017); https://doi.org/10.1016/j.cattod.2016.03.036
P. Yadav, M. Yadav, R. Gaur, R. Gupta, G. Arora, P. Rana, A. Srivastava and R.K. Sharma, ChemCatChem, 12, 2488 (2020); https://doi.org/10.1002/cctc.202000148
A. Solhy, R. Tahir, S. Sebti, R. Skouta, M. Bousmina, M. Zahouily and M. Larzek, Appl. Catal. A Gen., 374, 189 (2010); https://doi.org/10.1016/j.apcata.2009.12.008
S. Mandge, H.P. Singh, S.D. Gupta, N.S. Hari, Narayana Moorthy, Trends Appl. Sci. Res., 2, 52 (2007); https://doi.org/10.3923/tasr.2007.52.56
D.R. Palleros, J. Chem. Educ., 81, 1345 (2004); https://doi.org/10.1021/ed081p1345
S. Eddarir, N. Cotelle, Y. Bakkour and C. Rolando, Tetrahedron Lett., 44, 5359 (2003); https://doi.org/10.1016/S0040-4039(03)01140-7