Copyright (c) 2024 Tanjima laskar tarique
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Divergent Synthesis and in vitro Biological Evaluation of Novel Pyrazolyl Chalcones and Pyrazolyl Flavones
Corresponding Author(s) : Tanjima Tarique Laskar
Asian Journal of Chemistry,
Vol. 36 No. 7 (2024): Vol 36 Issue 7, 2024
Abstract
A total of sixteen flavonoids, eight each of pyrazolyl chalcones [IM-3(a-h)] and pyrazolyl flavones [IM-4(a-h)] were synthesized and tested for in vitro antidiabetic, antiarthritic, anticoagulant, anthelmintic, anti-inflammatory and antioxidant activities by various methods such as α-amylase inhibitory method, egg albumin denaturation method, prothrombin time method, paralysis and death time method, bovine serum denaturation method and DPPH radical scavenging activity method, respectively. Structural analysis of the synthesized chalcone and flavone derivatives was carried out by various characterization techniques such as IR, 1H NMR, 13C NMR, LC-MS and elemental analysis. Out of all the synthesized derivatives IM-3a containing dibenzyloxy groups had displayed the most promising activity in all the in vitro analysis with IC50 value ranging from 59.33 ± 10.26-144.44 ± 11.16 µg/mL. Compound IM-3a may prove to be a potential therapeutic option owing to its strong antidiabetic, antiarthritic, anticoagulant, anthelmintic, anti-inflammatory and and antioxidant properties.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- M.C. Dias, D.C. Pinto and A.M. Silva, Molecules, 26, 5377 (2021); https://doi.org/10.3390/molecules26175377
- C. Zhuang, W. Zhang, C. Sheng, W. Zhang, C. Xing and Z. Miao, Chem. Rev., 117, 7762 (2017); https://doi.org/10.1021/acs.chemrev.7b00020
- D.K. Mahapatra, S.K. Bharti and V. Asati, Eur. J. Med. Chem., 101, 496 (2015); https://doi.org/10.1016/j.ejmech.2015.06.052
- M.A. Rahim, M.M. Bhuiayan and M.M. Matin, J. Sci. Res., 12, 673 (2020); https://doi.org/10.3329/jsr.v12i4.45523
- K.V. Shcherbakov, M.A. Panova, Y.V. Burgart, V.V. Zarubaev, N.A. Gerasimova, N.P. Evstigneeva and V.I. Saloutin, J. Fluor. Chem., 249, 109857 (2021); https://doi.org/10.1016/j.jfluchem.2021.109857
- A. Kumar, R. Sharma and S.K. Singh, Lett. Appl. NanoBioScience, 10, 1760 (2021); https://doi.org/10.33263/LIANBS101.17601791
- B.S. Jayashree, A. Alam, D.V. Kumar and Y. Nayak, Indian J. Heterocycl. Chem., 19, 237 (2010).
- A. Kladna, P. Berczyñski, O.B. Dündar, M.C. Ünlüsoy, E. Sari, B. Bakinowska, I. Kruk and H.Y. Aboul-Enein, Future Med. Chem., 10, 2293 (2018); https://doi.org/10.4155/fmc-2018-0206
- X. Wang, Y. Cao, S. Chen, J. Lin, J. Bian and D. Huang, J. Agric. Food Chem., 69, 7285 (2021); https://doi.org/10.1021/acs.jafc.1c02015
- D. Isika, M. Çesme, F.J. Osonga and O.A. Sadik, RSC Adv., 10, 25046 (2020); https://doi.org/10.1039/D0RA04559D
- Y. Zhu, X. Yao, J. Long, R. Li, Y. Liu, Z. Yang and X. Zheng, Nat. Prod. Commun., 14, 1 (2019); https://doi.org/10.1177/1934578X1987892
- M. Khater, D. Ravishankar, F. Greco and H.M. Osborn, Future Med. Chem., 11, 2845 (2019); https://doi.org/10.4155/fmc-2019-0237
- N. Zhang, J. Yang, K. Li, J. Luo, S. Yang, J.R. Song, C. Chen and W.D. Pan, Molecules, 24, 2723 (2019); https://doi.org/10.3390/molecules24152723
- T. Constantinescu, C.N. Lungu and I. Lung, Molecules, 24, 1505 (2019); https://doi.org/10.3390/molecules24081505
- T.S. Tran, T.D. Tran, T.H. Tran, T.T. Mai, N.L. Nguyen, K.M. Thai and M.T. Le, Molecules, 25, 4064 (2020); https://doi.org/10.3390/molecules25184064
- S.S. Lim, H.S. Kim and D.U. Lee, Bull. Korean Chem. Soc., 28, 2495 (2007); https://doi.org/10.5012/bkcs.2007.28.12.2495
- E.U. Mughal, J. Ashraf, E.M. Hussein, Y. Nazir, A.S. Alwuthaynani, N. Naeem, A. Sadiq, R.I. Alsantali and S.A. Ahmed, ACS Omega, 7, 17444 (2022); https://doi.org/10.1021/acsomega.2c01841
- L.G. Sarbu, L.G. Bahrin, C. Babii, M. Stefan and M.L. Birsa, J. Appl. Microbiol., 127, 1282 (2019); https://doi.org/10.1111/jam.14271
- F.J. Osonga, A. Akgul, R.M. Miller, G.B. Eshun, I. Yazgan, A. Akgul and O.A. Sadik, ACS Omega, 4, 12865 (2019); https://doi.org/10.1021/acsomega.9b00077
- S.H. Hwang, H.Y. Kim, G. Zuo, Z. Wang, J.Y. Lee and S.S. Lim, Molecules, 23, 1752 (2018); https://doi.org/10.3390/molecules23071752
- P. Thirugnanasambantham, S. Viswanathan, C. Mythirayee, V. Krishnamurty, S. Ramachandran and L. Kameswaran, J. Ethnopharmacol., 28, 207 (1990); https://doi.org/10.1016/0378-8741(90)90030-W
- S.P. Viswanathan, S.K. Kulanthaivel, T. Nazimudeen, C. Vinayakam and C. Gopalakrishnan, Indian J. Pharm. Sci., 43, 159 (1981).
- G.H. Quan, H.S. Chae, H.H. Song, K.S. Ahn, H.K. Lee, Y.H. Kim, S.R. Oh and Y.W. Chin, Chem. Pharm. Bull., 61, 920 (2013); https://doi.org/10.1248/cpb.c13-00239
- T.C. Wang, Y.L. Chen, C.C. Tzeng, S.S. Liou, Y.L. Chang and C.M. Teng, Helv. Chim. Acta, 79, 1620 (1996); https://doi.org/10.1002/hlca.19960790612
- T.T. Cushnie and A.J. Lamb, Int. J. Antimicrob. Agents, 26, 343 (2005); https://doi.org/10.1016/j.ijantimicag.2005.09.002
- T. Farkhondeh, S. Samarghandian and F. Bafandeh, Cardiovasc. Hematol. Agents Med. Chem., 17, 17 (2019); https://doi.org/10.2174/1871525717666190114145137
- J.V. Faria, P.F. Vegi, A.G. Miguita, M.S. Dos Santos, N. Boechat and A.M. Bernardino, Bioorg. Med. Chem., 25, 5891 (2017); https://doi.org/10.1016/j.bmc.2017.09.035
- O. Alam, M.J. Naim, F. Nawaz, M.J. Alam and P. Alam, J. Pharm. Bioallied Sci., 8, 2 (2016); https://doi.org/10.4103/0975-7406.171694
- S.S. Momina and V. Swaroopa Ran, J. Young Pharm., 12(2s), s72 (2020); https://doi.org/10.5530/jyp.2020.12s.50
- T.G. Ajithkumar, L. Mathew, K.N. Sunilkumar, R. Rajagopal, A. Alfarhan, Y.O. Kim, H. Kim and H.-J. Kim, Saudi J. Biol. Sci., 27, 3301 (2020); https://doi.org/10.1016/j.sjbs.2020.10.008
- K. Chegu, K. Mounika, M. Rajeswari, N. Vanibala, P. Sujatha, P. Sridurga and D.B. Reddy, World J. Pharm. Pharm. Sci., 7, 904 (2018).
- S.D. Shruthi, S. Padmalatha Rai and Y.L. Ramachandra, Med. Chem. Res., 22, 2938 (2013); https://doi.org/10.1007/s00044-012-0295-4
- G.N. Anyasor, A.A. Okanlawon and B. Ogunbiyi, Clin. Phytosci., 5, 49 (2019); https://doi.org/10.1186/s40816-019-0137-8
- F. Shaheen, M. Ahmad, M.T.H. Khan, S. Jalil, A. Ejaz, M.N. Sultankhodjaev, M. Arfan, M.I. Choudhary and Atta-ur-Rahman, Phytochemistry, 66, 935 (2005); https://doi.org/10.1016/j.phytochem.2005.02.010
- P. Molyneux, J. Sci. Technol., 26, 211 (2004).
References
M.C. Dias, D.C. Pinto and A.M. Silva, Molecules, 26, 5377 (2021); https://doi.org/10.3390/molecules26175377
C. Zhuang, W. Zhang, C. Sheng, W. Zhang, C. Xing and Z. Miao, Chem. Rev., 117, 7762 (2017); https://doi.org/10.1021/acs.chemrev.7b00020
D.K. Mahapatra, S.K. Bharti and V. Asati, Eur. J. Med. Chem., 101, 496 (2015); https://doi.org/10.1016/j.ejmech.2015.06.052
M.A. Rahim, M.M. Bhuiayan and M.M. Matin, J. Sci. Res., 12, 673 (2020); https://doi.org/10.3329/jsr.v12i4.45523
K.V. Shcherbakov, M.A. Panova, Y.V. Burgart, V.V. Zarubaev, N.A. Gerasimova, N.P. Evstigneeva and V.I. Saloutin, J. Fluor. Chem., 249, 109857 (2021); https://doi.org/10.1016/j.jfluchem.2021.109857
A. Kumar, R. Sharma and S.K. Singh, Lett. Appl. NanoBioScience, 10, 1760 (2021); https://doi.org/10.33263/LIANBS101.17601791
B.S. Jayashree, A. Alam, D.V. Kumar and Y. Nayak, Indian J. Heterocycl. Chem., 19, 237 (2010).
A. Kladna, P. Berczyñski, O.B. Dündar, M.C. Ünlüsoy, E. Sari, B. Bakinowska, I. Kruk and H.Y. Aboul-Enein, Future Med. Chem., 10, 2293 (2018); https://doi.org/10.4155/fmc-2018-0206
X. Wang, Y. Cao, S. Chen, J. Lin, J. Bian and D. Huang, J. Agric. Food Chem., 69, 7285 (2021); https://doi.org/10.1021/acs.jafc.1c02015
D. Isika, M. Çesme, F.J. Osonga and O.A. Sadik, RSC Adv., 10, 25046 (2020); https://doi.org/10.1039/D0RA04559D
Y. Zhu, X. Yao, J. Long, R. Li, Y. Liu, Z. Yang and X. Zheng, Nat. Prod. Commun., 14, 1 (2019); https://doi.org/10.1177/1934578X1987892
M. Khater, D. Ravishankar, F. Greco and H.M. Osborn, Future Med. Chem., 11, 2845 (2019); https://doi.org/10.4155/fmc-2019-0237
N. Zhang, J. Yang, K. Li, J. Luo, S. Yang, J.R. Song, C. Chen and W.D. Pan, Molecules, 24, 2723 (2019); https://doi.org/10.3390/molecules24152723
T. Constantinescu, C.N. Lungu and I. Lung, Molecules, 24, 1505 (2019); https://doi.org/10.3390/molecules24081505
T.S. Tran, T.D. Tran, T.H. Tran, T.T. Mai, N.L. Nguyen, K.M. Thai and M.T. Le, Molecules, 25, 4064 (2020); https://doi.org/10.3390/molecules25184064
S.S. Lim, H.S. Kim and D.U. Lee, Bull. Korean Chem. Soc., 28, 2495 (2007); https://doi.org/10.5012/bkcs.2007.28.12.2495
E.U. Mughal, J. Ashraf, E.M. Hussein, Y. Nazir, A.S. Alwuthaynani, N. Naeem, A. Sadiq, R.I. Alsantali and S.A. Ahmed, ACS Omega, 7, 17444 (2022); https://doi.org/10.1021/acsomega.2c01841
L.G. Sarbu, L.G. Bahrin, C. Babii, M. Stefan and M.L. Birsa, J. Appl. Microbiol., 127, 1282 (2019); https://doi.org/10.1111/jam.14271
F.J. Osonga, A. Akgul, R.M. Miller, G.B. Eshun, I. Yazgan, A. Akgul and O.A. Sadik, ACS Omega, 4, 12865 (2019); https://doi.org/10.1021/acsomega.9b00077
S.H. Hwang, H.Y. Kim, G. Zuo, Z. Wang, J.Y. Lee and S.S. Lim, Molecules, 23, 1752 (2018); https://doi.org/10.3390/molecules23071752
P. Thirugnanasambantham, S. Viswanathan, C. Mythirayee, V. Krishnamurty, S. Ramachandran and L. Kameswaran, J. Ethnopharmacol., 28, 207 (1990); https://doi.org/10.1016/0378-8741(90)90030-W
S.P. Viswanathan, S.K. Kulanthaivel, T. Nazimudeen, C. Vinayakam and C. Gopalakrishnan, Indian J. Pharm. Sci., 43, 159 (1981).
G.H. Quan, H.S. Chae, H.H. Song, K.S. Ahn, H.K. Lee, Y.H. Kim, S.R. Oh and Y.W. Chin, Chem. Pharm. Bull., 61, 920 (2013); https://doi.org/10.1248/cpb.c13-00239
T.C. Wang, Y.L. Chen, C.C. Tzeng, S.S. Liou, Y.L. Chang and C.M. Teng, Helv. Chim. Acta, 79, 1620 (1996); https://doi.org/10.1002/hlca.19960790612
T.T. Cushnie and A.J. Lamb, Int. J. Antimicrob. Agents, 26, 343 (2005); https://doi.org/10.1016/j.ijantimicag.2005.09.002
T. Farkhondeh, S. Samarghandian and F. Bafandeh, Cardiovasc. Hematol. Agents Med. Chem., 17, 17 (2019); https://doi.org/10.2174/1871525717666190114145137
J.V. Faria, P.F. Vegi, A.G. Miguita, M.S. Dos Santos, N. Boechat and A.M. Bernardino, Bioorg. Med. Chem., 25, 5891 (2017); https://doi.org/10.1016/j.bmc.2017.09.035
O. Alam, M.J. Naim, F. Nawaz, M.J. Alam and P. Alam, J. Pharm. Bioallied Sci., 8, 2 (2016); https://doi.org/10.4103/0975-7406.171694
S.S. Momina and V. Swaroopa Ran, J. Young Pharm., 12(2s), s72 (2020); https://doi.org/10.5530/jyp.2020.12s.50
T.G. Ajithkumar, L. Mathew, K.N. Sunilkumar, R. Rajagopal, A. Alfarhan, Y.O. Kim, H. Kim and H.-J. Kim, Saudi J. Biol. Sci., 27, 3301 (2020); https://doi.org/10.1016/j.sjbs.2020.10.008
K. Chegu, K. Mounika, M. Rajeswari, N. Vanibala, P. Sujatha, P. Sridurga and D.B. Reddy, World J. Pharm. Pharm. Sci., 7, 904 (2018).
S.D. Shruthi, S. Padmalatha Rai and Y.L. Ramachandra, Med. Chem. Res., 22, 2938 (2013); https://doi.org/10.1007/s00044-012-0295-4
G.N. Anyasor, A.A. Okanlawon and B. Ogunbiyi, Clin. Phytosci., 5, 49 (2019); https://doi.org/10.1186/s40816-019-0137-8
F. Shaheen, M. Ahmad, M.T.H. Khan, S. Jalil, A. Ejaz, M.N. Sultankhodjaev, M. Arfan, M.I. Choudhary and Atta-ur-Rahman, Phytochemistry, 66, 935 (2005); https://doi.org/10.1016/j.phytochem.2005.02.010
P. Molyneux, J. Sci. Technol., 26, 211 (2004).