Abstract
Novel pyrrolo[2,3-d]pyrimidine derivatives were synthesized starting from 2-amino-5-aryl-1-phenyl-1H-pyrrole-3-carbonitriles, and their structures were elucidated by spectral data (IR, NMR, MS) and elemental analyses. Representative compounds were evaluated for their in vitro apoptotic activities against human lung cancer using doxorubicin as a reference drug. The antiproliferative effect of these compounds was measured by the MTT assay on human lung adenocarcinoma (A549). Five compounds exhibited excellent anticancer activity against human lung cancer cell line with IC50 values of 96.5, 99.79, 102.55, 109.24, and 111.33 μg/mL.
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REFERENCES
Bayat, M. and Nasri, S., J. Mol. Struct., 2018, vol. 1154, p. 366. https://doi.org/10.1016/j.molstruc.2017.10.056
Anand, P., Kunnumakara, A.B., Sundaram, C., Harikumar, K.B., Tharakan, S.T., Lai, O.S., and Aggarwal, B.B., J. Pharm. Res., 2008, vol. 25, p. 2097. https://doi.org/10.1007/s11095-008-9661-9
Raju, K.S., AnkiReddy, S., Sabitha, G., Krishna, V.S., Sriram, D., Reddy, K.B., and Sagurthi, S.R., Bioorg. Med. Chem. Lett., 2019, vol. 29, p. 284. https://doi.org/10.1016/j.bmcl.2018.11.036
Kumar, R.N., Dev, G.J., Ravikumar, N., Swaroop, D.K., Debanjan, B., Bharath, G., and Rao, A.G., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 2927. https://doi.org/10.1016/j.bmcl.2016.04.038
Narsimha, S., Kumar, N.S., Swamy, B.K., Reddy, N.V., Hussain, S.A., and Rao, M.S., Bioorg. Med. Chem. Lett., 2016, vol. 26, p. 1639. https://doi.org/10.1016/j.bmcl.2016.01.055
Shalini, K., Kumar, N., Drabu, S., and Sharma, P.K., Beilstein J. Org. Chem., 2011, vol. 7, p. 668. https://doi.org/10.3762/bjoc.7.79
Malagu, K., Duggan, H., Menear, K., Hummersone, M., Gomez, S., Bailey, C., and Pass, M., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 5950. https://doi.org/10.1016/j.bmcl.2009.08.038
Mohammed, I., Kummetha, I.R., Singh, G., Sharova, N., Lichinchi, G., Dang, J., and Rana, T.M., J. Med. Chem., 2016, vol. 59, p. 7677. https://doi.org/10.1021/acs.jmedchem.6b00247
Dheer, D., Singh, V., and Shankar, R., Bioorg. Chem., 2017, vol. 71, p. 30. https://doi.org/10.1016/j.bioorg.2017.01.010
Shafi, S., Alam, M.M., Mulakayala, N., Mulakayala, C., Vanaja, G., Kalle, A.M., and Alam, M.S., Eur. J. Med. Chem., 2012, vol. 49, p. 324. https://doi.org/10.1016/j.ejmech.2012.01.032
Kamal, A., Shankaraiah, N., Devaiah, V., Reddy, K.L., Juvekar, A., Sen, S., and Zingde, S., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 1468. https://doi.org/10.1016/j.bmcl.2007.12.063
Duan, Y.C., Ma, Y.C., Zhang, E., Shi, X.J., Wang, M.M., Ye, X.W., and Liu, H.M., Eur. J. Med. Chem., 2013, vol. 62, p. 11. https://doi.org/10.1016/j.ejmech.2012.12.046
Hahn, F., Hutterer, C., Henry, C., Hamilton, S.T., Strojan, H., Kraut, A., and Pfizer, J., Antiviral Res., 2018, vol. 159, p. 84. https://doi.org/10.1016/j.antiviral.2018.09.012
Zhang, S., Xu, Z., Gao, C., Ren, Q.C., Chang, L., Lv, Z.S., and Feng, L.S., Eur. J. Med. Chem., 2017, vol. 138, p. 501. https://doi.org/10.1016/j.ejmech.2017.06.051
Shaikh, M.H., Subhedar, D.D., Nawale, L., Sarkar, D., Khan, F.A.K., Sangshetti, J.N., and Shingate, B.B., MedChemComm, 2015, vol. 6, p. 1104. https://doi.org/10.1039/C5MD00057B
Fayed, E.A., Sabour, R., Harras, M.F., and Mehany, A.B., Med. Chem. Res., 2019, vol. 28, p. 1284. https://doi.org/10.1007/s00044-019-02373-x
Ghorab, M.M., Alsaid, M.S., Ceruso, M., Nissan, Y.M., and Supuran, C.T., Bioorg. Med. Chem., 2014, vol. 22, p. 3684. https://doi.org/10.1016/j.bmc.2014.05.009
Bernal, C.C., Vesga, L.C., Mendez-Sánchez, S.C., and Bohórquez, A.R.R., Med. Chem. Res., 2020, vol. 29, p. 675. https://doi.org/10.1007/s00044-020-02513-8
Kilic-Kurt, Z., Bakar-Ates, F., Aka, Y., and Kutuk, O., Bioorg. Chem., 2019, vol. 83, p. 511. https://doi.org/10.1016/j.bioorg.2018.10.060
Su, Z., Yang, Z., Xie, L., DeWitt, J.P., and Chen, Y., Cell Death Differ., 2016, vol. 23, p. 748.
Beyer, C.E., Dwyer, J.M., Piesla, M.J., Platt, B.J., Shen, R., Rahman, Z., and Whiteside, G.T., Neurobiol. Dis., 2010, vol. 39, p. 148. https://doi.org/10.1016/j.nbd.2010.03.020
Blank, M. and Shiloh, Y., Cell Cycle, 2007, vol. 6, p. 686. https://doi.org/10.4161/cc.6.6.3990
Hilmy, K.M.H. and Pedersen, E.B., Justus Liebigs Ann. Chem., 1989, vol. 1989, p. 1145. https://doi.org/10.1002/jlac.198919890285
Hilmy, K.M.H., Arch. Pharm., 2004, vol. 337, p. 15. https://doi.org/10.1002/ardp.200300773
Hilmy, K.M.H., Arch. Pharm., 2006, vol. 339, p. 174. https://doi.org/10.1002/ardp.200500162
Hilmy, K.M.H., Khalifa, M.M., Hawata, M.A.A., and Keshk, R.M.A., Eur. J. Med. Chem., 2010, vol. 45, p. 5243. https://doi.org/10.1016/j.ejmech.2010.08.043
Bahuguna, A., Khan, I., Bajpai, V.K., and Kang, S.C., Bangladesh J. Pharmacol., 2017, vol. 12, no. 2, p. 115. https://doi.org/10.3329/bjp.v12i2.30892
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Hilmy, K.M.H., Kishk, F.N.M., Shahen, E.B.A. et al. Synthesis and Biological Evaluation of Pyrrolo[2,3-d]pyrimidine Derivatives as Novel Apoptotic Agents for Human Lung Cancer Cells. Russ J Org Chem 59, 1184–1191 (2023). https://doi.org/10.1134/S1070428023070096
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DOI: https://doi.org/10.1134/S1070428023070096