Copyright (c) 2024 Sandeep Singh, Rajeev Kumar Sharma , Aishwarya Singh , Manoj Garg, R Ramajayam Ramachandran
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Biological Evaluation of vicinal-Diaryl Pyrazole Ethyl Carboxylate Analogs as Antiproliferative Agent against Pancreatic Cancer
Corresponding Author(s) : R. Ramajayam
Asian Journal of Chemistry,
Vol. 36 No. 3 (2024): Vol 36 Issue 3, 2024
Abstract
vicinal Diaryl scaffold possessing various heterocycles displayed versatile pharmacological activities ranging from antibacterial to antiviral. Herein, the synthesis of novel vicinal diaryl pyrazole ethyl carboxylate analogs as central ring and evaluated for their antiproliferative activity against pancreatic cancer line, PANC-1. Among the synthesized 27 compounds, six compounds displayed the IC50 value for antiproliferative activity in single digit micromolar. The cytotoxicity results of the synthesized compounds especially compound 25 (IC50 = 4.8 µM) confirms that these analogs may require further investigation.
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- Y.J. Wu, Progress in Heterocyclic Chem., 24, 1 (2012); https://doi.org/10.1016/B978-0-08-096807-0.00001-4
- J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
- E. Kabir and M. Uzzaman, Results Chem., 4, 100606 (2022); https://doi.org/10.1016/j.rechem.2022.100606
- G. Li, Y. Cheng, C. Han, C. Song, N. Huang and Y. Du, RSC Med. Chem., 13, 1300 (2022); https://doi.org/10.1039/D2MD00206J
- N. Chopra, D. Kaur and G. Chopra, ACS Omega, 3, 12688 (2018); https://doi.org/10.1021/acsomega.8b01523
- M.I. El-Gamal, S.O. Zaraei, M.M. Madkour and H.S. Anbar, Molecules, 27, 330 (2022); https://doi.org/10.3390/molecules27010330
- V. Singhania, C.B. Nelson, M. Reamey, E. Morin, R.D. Kavthe and B.H. Lipshutz, Org. Lett., 25, 4308 (2023); https://doi.org/10.1021/acs.orglett.3c01380
- F. Xu, J. Chen, X. Xie, P. Cheng, Z. Yu and W. Su, Org. Process Res. Dev., 24, 2252 (2020); https://doi.org/10.1021/acs.oprd.0c00302
- L. Yao, N. Mustafa, E.C. Tan, A. Poulsen, P. Singh, M.D. Duong-Thi, J.X.T. Lee, P.M. Ramanujulu, W.J. Chng, J.J.Y. Yen, S. Ohlson and B.W. Dymock, J. Med. Chem., 60, 8336 (2017); https://doi.org/10.1021/acs.jmedchem.7b00678
- T. Sugawara, S.J. Baumgart, E. Nevedomskaya, K. Reichert, H. Steuber, P. Lejeune, D. Mumberg and B. Haendler, Int. J. Cancer, 145, 1382 (2019); https://doi.org/10.1002/ijc.32242
- R. Ramajayam, R. Giridhar, M.R. Yadav, R. Balaraman, H. Djaballah, D. Shum and C. Radu, Eur. J. Med. Chem., 43, 2004 (2008); https://doi.org/10.1016/j.ejmech.2007.11.023
- R. Ramajayam, Eur. J. Med. Chem., 162, 1 (2019); https://doi.org/10.1016/j.ejmech.2018.10.054
- L. Grau, R. Soucek and M.D. Pujol, Eur. J. Med. Chem., 246, 114962 (2023); https://doi.org/10.1016/j.ejmech.2022.114962
- M.V. Berridge, P.M. Herst and A.S. Tan, Biotechnol. Annu. Rev., 11, 127 (2005); https://doi.org/10.1016/S1387-2656(05)11004-7
- T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997); https://doi.org/10.1021/jm960803q
- K.R. Abdellatif, M.A. Chowdhury, Y. Dong and E.E. Knaus, Bioorg. Med. Chem., 16, 6528 (2008); https://doi.org/10.1016/j.bmc.2008.05.028
- F. Denizot and R. Lang, J. Immunol. Methods, 89, 271 (1986); https://doi.org/10.1016/0022-1759(86)90368-6
References
Y.J. Wu, Progress in Heterocyclic Chem., 24, 1 (2012); https://doi.org/10.1016/B978-0-08-096807-0.00001-4
J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
E. Kabir and M. Uzzaman, Results Chem., 4, 100606 (2022); https://doi.org/10.1016/j.rechem.2022.100606
G. Li, Y. Cheng, C. Han, C. Song, N. Huang and Y. Du, RSC Med. Chem., 13, 1300 (2022); https://doi.org/10.1039/D2MD00206J
N. Chopra, D. Kaur and G. Chopra, ACS Omega, 3, 12688 (2018); https://doi.org/10.1021/acsomega.8b01523
M.I. El-Gamal, S.O. Zaraei, M.M. Madkour and H.S. Anbar, Molecules, 27, 330 (2022); https://doi.org/10.3390/molecules27010330
V. Singhania, C.B. Nelson, M. Reamey, E. Morin, R.D. Kavthe and B.H. Lipshutz, Org. Lett., 25, 4308 (2023); https://doi.org/10.1021/acs.orglett.3c01380
F. Xu, J. Chen, X. Xie, P. Cheng, Z. Yu and W. Su, Org. Process Res. Dev., 24, 2252 (2020); https://doi.org/10.1021/acs.oprd.0c00302
L. Yao, N. Mustafa, E.C. Tan, A. Poulsen, P. Singh, M.D. Duong-Thi, J.X.T. Lee, P.M. Ramanujulu, W.J. Chng, J.J.Y. Yen, S. Ohlson and B.W. Dymock, J. Med. Chem., 60, 8336 (2017); https://doi.org/10.1021/acs.jmedchem.7b00678
T. Sugawara, S.J. Baumgart, E. Nevedomskaya, K. Reichert, H. Steuber, P. Lejeune, D. Mumberg and B. Haendler, Int. J. Cancer, 145, 1382 (2019); https://doi.org/10.1002/ijc.32242
R. Ramajayam, R. Giridhar, M.R. Yadav, R. Balaraman, H. Djaballah, D. Shum and C. Radu, Eur. J. Med. Chem., 43, 2004 (2008); https://doi.org/10.1016/j.ejmech.2007.11.023
R. Ramajayam, Eur. J. Med. Chem., 162, 1 (2019); https://doi.org/10.1016/j.ejmech.2018.10.054
L. Grau, R. Soucek and M.D. Pujol, Eur. J. Med. Chem., 246, 114962 (2023); https://doi.org/10.1016/j.ejmech.2022.114962
M.V. Berridge, P.M. Herst and A.S. Tan, Biotechnol. Annu. Rev., 11, 127 (2005); https://doi.org/10.1016/S1387-2656(05)11004-7
T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997); https://doi.org/10.1021/jm960803q
K.R. Abdellatif, M.A. Chowdhury, Y. Dong and E.E. Knaus, Bioorg. Med. Chem., 16, 6528 (2008); https://doi.org/10.1016/j.bmc.2008.05.028
F. Denizot and R. Lang, J. Immunol. Methods, 89, 271 (1986); https://doi.org/10.1016/0022-1759(86)90368-6