Abstract
A series of abietic acid analogs modified with a triazole moiety were synthesized using Huisgen 1,3-dipolar cycloaddition in order to obtain potent antitumor agents. The synthesized compounds and starting materials were tested in vitro against four human cancer cell lines, MDA-MB-231 and MCF-7 (human breast cancer cells), A549 (human lung cancer), PC3 (human prostate cancer), and FR2 (non-tumor human breast epithelial cell line) by MTT assay. Some of the synthesized analogs showed better biological profiles than that of the precursors. The most active compound (4-hydroxyphenyl derivative) showed an IC50 value of 35.4 µM against MDA-MB-231 cancer cell line.
REFERENCES
Mathers, C.D. and Loncar, D., PLoS Med., 2006, vol. 3, article ID e442. https://doi.org/10.1371/journal.pmed.0030442
Bernabeu, E., Cagel, M., Lagomarsino, E., Moretton, M., and Chiappetta, D.A., Int. J. Pharm., 2017, vol. 526, p. 474. https://doi.org/10.1016/j.ijpharm.2017.05.016
Qiao, L., Han, M., Gao, S., Shao, X., Wang, X., Sun, L., Fu, X., and Wei, Q., J. Mater. Chem. B, 2020, vol. 8, p. 6333. https://doi.org/10.1039/D0TB01260B
Shan, L., Liu, M., Wu, C., Zhao, L., Li, S., Xu, L., Cao, W., Gao, G., and Gu, Y., Int. J. Nanomed., 2015, vol. 10, p. 5571. https://doi.org/10.2147/IJN.S85402
Cheng, J., Fu, S., Qin, Z., Han, Y., and Yang, X., J. Mater. Chem. B, 2021, vol. 9, p. 2674. https://doi.org/10.1039/D0TB02995E
Zhao, Q., Zhang, H., Zhao, H., Liu, J., Liu, J., Chen, Z., Li, B., Liao, X., Regenstein, J.M., Wang, J., and Yang, X., ACS Appl. Mater. Interfaces, 2020, vol. 12, p. 8751. https://doi.org/10.1021/acsami.9b21460
Wang, J., Zhao, H., Zhi, K., and Yang, X., ACS Appl. Mater. Interfaces, 2020, vol. 12, p. 6827. https://doi.org/10.1021/acsami.9b18443
Zhi, K., Wang, J., Zhao, H., and Yang, X., Acta Pharm. Sin. B, 2020, vol. 10, p. 913. https://doi.org/10.1016/j.apsb.2019.09.009
Payne, D.J., Gwynn, M.N., Holmes, D.J., and Pompliano, D.L., Nat. Rev. Drug Discovery, 2007, vol. 6, p. 29. https://doi.org/10.1038/nrd2201
Cragg, G.M., Katz, F., Newman, D.J., and Rosenthal, J., Nat. Prod. Rep., 2012, vol. 29, p. 1407. https://doi.org/10.1039/C2NP20091K
Jordan, M.A. and Wilson, L., Nat. Rev. Cancer, 2004, vol. 4, p. 253. https://doi.org/10.1038/nrc1317
D’Incalci, M. and Galmarini, C.M., Mol. Cancer Ther., 2010, vol. 9, p. 2157. https://doi.org/10.1158/1535-7163.MCT-10-0263
Grivas, P.D., Kiaris, H., and Papavassiliou, A.G., Trends Mol. Med., 2011, vol. 17, p. 537. https://doi.org/10.1016/j.molmed.2011.06.005
Baltz, R.H., Curr. Opin. Pharmacol., 2008, vol. 8, p. 557. https://doi.org/10.1016/j.coph.2008.04.008
Huigens, R.W. III, Morrison, K.C., Hicklin, R.W., Flood, T.A., Jr., Richter, M.F., and Hergenrother, P.J., Nat. Chem., 2013, vol. 5, p. 195. https://doi.org/10.1038/nchem.1549
Rafferty, R.J., Hicklin, R.W., Maloof, K.A., and Hergenrother, P.J., Angew. Chem., 2014, vol. 126, p. 224. https://doi.org/10.1002/ange.201308743
He, X.P., Zeng, Y.L., Zang, Y., Li, J., Field, R.A., and Chen, G.R., Carbohydr. Res., 2016, vol. 429, p. 1. https://doi.org/10.1016/j.carres.2016.03.022
Gonzalez, M.A., Correa-Royero, J., Agudelo, L., Mesa, A., and Betancur-Galvis, L., Eur. J. Med. Chem., 2009, vol. 44, p. 2468. https://doi.org/10.1016/j.ejmech.2009.01.014
Hou, W., Luo, Z., Zhang, G., Cao, D., Li, D., Ruan, H., Ruan, B.H., Su, L., and Xu, H., Eur. J. Med. Chem., 2017, vol. 138, p. 1042. https://doi.org/10.1016/j.ejmech.2017.07.049
Li, F.Y., Wang, X., Duan, W.G., and Lin, G.S., Molecules, 2017, vol. 22, article no. 1087. https://doi.org/10.3390/molecules22071087
Abdulla, M.M., Monatsh. Chem., 2008, vol. 139, p. 697. https://doi.org/10.1007/s00706-007-0804-1
Xu, H., Liu, L., Fan, X., Zhang, G., Li, Y., and Jiang, B., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 505. https://doi.org/10.1016/j.bmcl.2016.12.032
Liu, X., Chen, W., Liu, Q., and Dai, J., OncoTargets Ther., 2019, vol. 12, p. 4825. https://doi.org/10.2147/OTT.S199161
Kumar, S., Sharma, B., Mehra, V., and Kumar, V., Eur. J. Med. Chem., 2021, vol. 212, article ID 113069. https://doi.org/10.1016/j.ejmech.2020.113069
Häring, M., Nandi, S.K., Rodríguez-López, J., Haldar, D., Martín, V.S., Lozano-Gorrín, A.D., Saldías, C., and Díaz, D.D., ACS Omega, 2019, vol. 4, p. 2111. https://doi.org/10.1021/acsomega.8b03292
Chang, J.J., Wang, Y., Zhang, H.Z., Zhou, C.H., Geng, R.X., and Ji, Q.G., Chem. J. Chin. Univ., 2011, vol. 32, p. 1970.
Fray, M.J., Bull, D.J., Carr, C.L., Gautier, E.C., Mowbray, C.E., and Stobie, A., J. Med. Chem., 2001, vol. 44, p. 1951. https://doi.org/10.1021/jm001124p
Smith, G., Glaser, M., Perumal, M., Nguyen, Q.D., Shan, B., Årstad, E., and Aboagye, E.O., J. Med. Chem., 2008, vol. 51, p. 8057. https://doi.org/10.1021/jm801107u
Yim, C.B., Dijkgraaf, I., Merkx, R., Versluis, C., Eek, A., Mulder, G.E., Rijkers, D.T., Boerman, O.C., and Liskamp, R.M., J. Med. Chem., 2010, vol. 53, p. 3944. https://doi.org/10.1021/jm100246m
Vatmurge, N.S., Hazra, B.G., Pore, V.S., Shirazi, F., Chavan, P.S., and Deshpande, M.V., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 2043. https://doi.org/10.1016/j.bmcl.2008.01.102
Vatmurge, N.S., Hazra, B.G., Pore, V.S., Shirazi, F., Deshpande, M.V., Kadreppa, S., Chattopadhyay, S., and Gonnade, R.G., Org. Biomol. Chem., 2008, vol. 6, p. 3823. https://doi.org/10.1039/B809221D
Kategaonkar, A.H., Shinde, P.V., Kategaonkar, A.H., Pasale, S.K., Shingate, B.B., and Shingare, M.S., Eur. J. Med. Chem., 2010, vol. 45, p. 3142. https://doi.org/10.1016/j.ejmech.2010.04.002
Somu, R.V., Boshoff, H., Qiao, C., Bennett, E.M., Barry, C.E., and Aldrich, C.C., J. Med. Chem., 2006, vol. 49, p. 31. https://doi.org/10.1021/jm051060o
Costa, M.S., Boechat, N., Rangel, E.A., Da Silva, F.D.C., De Souza, A.M., Rodrigues, C.R., Castro, H.C., Junior, I.N., Lourenço, M.C.S., Wardell, S.M., and Ferreira, V.F., Bioorg. Med. Chem., 2006, vol. 14, p. 8644. https://doi.org/10.1016/j.bmc.2006.08.019
Tripathi, R.P., Yadav, A.K., Ajay, A., Bisht, S.S., Chaturvedi, V., and Sinha, S.K., Eur. J. Med. Chem., 2010, vol. 45, p. 142. https://doi.org/10.1016/j.ejmech.2009.09.036
Whiting, M., Tripp, J.C., Lin, Y.C., Lindstrom, W., Olson, A.J., Elder, J.H., Sharpless, K.B., and Fokin, V.V., J. Med. Chem., 2006, vol. 49, p. 7697. https://doi.org/10.1021/jm060754+
Saito, Y., Escuret, V., Durantel, D., Zoulim, F., Schinazi, R.F., and Agrofoglio, L.A., Bioorg. Med. Chem., 2003, vol. 11, p. 3633. https://doi.org/10.1016/S0968-0896(03)00349-3
Mohapatra, D.K., Maity, P.K., Shabab, M., and Khan, M.I., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 5241. https://doi.org/10.1016/j.bmcl.2009.06.107
Tripathi, V.K., Singh, J., Ara, T., Koul, S., Farooq, S., and Kaul, A., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 4243. https://doi.org/10.1016/j.bmcl.2014.07.031
Ganaie, B.A., Shahid, M., Rashid, A., Ara, T., Ahmad Banday, J., Malik, F. and Bhat, B.A., Chem. Biodiversity, 2021., vol. 18, article ID e2100292. https://doi.org/10.1002/cbdv.202100292
Ali, G., Dangroo, N.A., Raheem, S., Naqvi, T., Ara, T., and Rizvi, M.A., Acta Chim. Slov., 2020, vol. 67, p. 195. https://doi.org/10.17344/acsi.2019.5348
Masood-ur-Rahman, Bhat, K.A., and Ara, T., J. Phytopharmacol., 2017, vol. 6, p. 227. https://doi.org/10.31254/phyto.2017.6405
Ganaie, B.A., Banday, J.A., Bhat, B.A., and Ara, T., Russ. J. Org. Chem., 2021, vol. 57, p. 2039. https://doi.org/10.1134/S1070428021120216
Rather, Z.K., Banday, J.A., and Chisti, H.N., Russ. J. Org. Chem., 2021, vol. 57, p. 986. https://doi.org/10.1134/S1070428021060154
Bhat, K.A., Lone, S.H., and Malik, F.A., Arab. J. Chem., 2019. vol. 12, p. 3479. https://doi.org/10.1016/j.arabjc.2015.10.009
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Supplementary information
Rights and permissions
About this article
Cite this article
Ali, G., Ara, T. Design, Synthesis, and In Vitro Anticancer Activity of Triazolyl Analogs of Abietic Acid. Russ J Org Chem 59, 142–149 (2023). https://doi.org/10.1134/S1070428023010153
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428023010153