Abstract
We have designed and synthesized a new series of amide derivatives of thiazolo[5,4-d]pyrimidines (10a-j) and their structures were characterized by 1H NMR, 13C NMR and mass spectral data. Furthermore, all compounds were evaluated for in vitro cytotoxicity effects against four human cancer cell lines such as PC3 (prostate cancer), A549 (lung cancer), MCF-7 (breast cancer) and DU-145 (prostate cancer) by employing MTT assay. The cytotoxicity effects of the amide derivatives (10a-j) were compared with etoposide utilized as the positive control. Among them, five compounds 10a, 10b, 10c, 10h and 10j possessed significant cytotoxicity properties as compared with etoposide.
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S. J. Vaghasia, V. H. Shah, J. Serb. Chem. Soc., 72(2), 109 – 117 (2007).
G. B. Elion, W. H. Lange, and G. H. Hitchings, J. Am. Chem. Soc., 78(12), 2858 – 2863 (1956).
S. Kolb, O. Mondésert, M.-L. Goddard, et al., Chem. Med. Chem., 4(4), 633 – 648 (2009).
A. A. Bekhit, H. T. Y. Fahmy, S. A. F. Rostom, et al., Eur. J. Med. Chem., 38(1), 27 – 36 (2003).
M. Y. Jang, S. De Jonghe, K. Segers, et al., Bioorg. Med. Chem., 19(1), 702 – 714 (2011).
H. T. Y. Fahmy, S. A. F. Rostom, M. N. Saudi, et al., Arch. Pharm. Pharm. Med. Chem., 336(4 – 5), 216 – 225 (2003).
D. P. Sutherlin, D. Sampath, M. Berry, et al., J. Med. Chem., 53(3), 1086 – 1097 (2010).
A. F. Lewis, J. C. Drach, S. M. Fennewal, et al., Antimicrob. Agents Chemother., 38(12), 2889 – 2895 (1994).
R. W. A. Luke, C. D. Jones, W. McCoull, et al., WO 2004013141, Astrazeneca (2004).
Y. Yonetoku, K. Negoro, K. Onda, et al., WO 2006040966, Astellas Pharma Inc. (2006).
G. Nordvall, T. Rein, D. Sohn, et al., WO 2005033115, Astrazeneca (2005).
J. Liu, A. E. Fitzgerald, A. D. Lebsack, et al., Org. Process. Res. Dev., 15(2), 382 – 388 (2011).
M. Y. Jang, Y. Lin, S. De Jonghe, et al., J. Med. Chem., 54(2), 655 – 668 (2011).
F. Giordanetto, B. Kull, A. Dellsen, Bioorg. Med. Chem. Lett., 21(2), 829 – 835 (2011).
F. Varano, D. Catarzi, L. Squarcialupi, Eur. J. Med. Chem., 96, 105 – 121 (2015).
Z. Nowakowska, Eur. J. Med. Chem., 42(2), 125 – 137 (2007).
J. Quintin, J. Desrivot, S. Thoret, et al., Bioorg. Med. Chem. Lett., 19(1), 167 – 169 (2009).
O. Prakash, A. Kumar, A. Sadana, et al., Tetrahedron, 61(27), 6642 – 6651 (2005).
Y. R. Prasad, A. L. Rao, L. Prasoona, et al., Bioorg. Med. Chem. Lett., 15(22), 5030 – 5034 (2005).
K. L. Lahtchev, D. I. Batovska, S. P. Parushev, et al., Eur. J. Med. Chem., 43(10), 2220–2228 (2008).
J. Rojas, M. Payá, J. N. Domínguez, et al., Eur. J. Pharmacol., 465(1 – 2), 183–189 (2003).
P. M. Sivakumar, S. Ganesan, P. Veluchamy, et al., Chem. Biol. Drug Des., 76(5), 407 – 411 (2010).
M. Satyanarayana, P. Tiwari, B. K. Tripathi, et al., Bioorg. Med. Chem., 12(15), 883 – 889 (2004).
M. L. Go, X. Wu, X. L. Liu, Curr. Med. Chem., 12(4), 481 – 499 (2005).
C. Furman, J. Lebeau, J. C. Fruchart, et al., J. Biochem. Mol. Toxicol., 15(5), 270 – 278 (2001).
Y. M. Lin, M. T. Flavin, L. M. Zhou, et al., Bioorg. Med. Chem., 10(8), 2795 – 2802 (2002).
M. Larsen, H. Kromannn, A. Kharazmi, et al., Bioorg. Med. Chem. Lett., 15(21), 4858 – 4861 (2005)
M. P. Neves, S. Cravo, R. T. Lima, et al., Bioorg. Med. Chem., 20(1), 25 – 33 (2012).
S. F. Nielsen, S. B. Christensen, G. Cruciani, et al., J. Med. Chem., 41(24), 4819 – 4832 (1998).
S. Ducki, R. Forrest, J. A. Hadfield, et al., Bioorg. Med. Chem. Lett., 8(9), 1051 – 1056 (1998).
A. Kamal, N. Shankaraiah, S. Prabhakar, et al., Bioorg. Med. Chem. Lett., 18(7), 2434 – 2439 (2008).
A. Modzelewska, C. Pettit, G. Achanta, et al., Bioorg. Med. Chem., 14(10), 3491 – 3495 (2006).
P. Jayaseelan, E. Akila, M. Usha Rani, et al., J. Saudi Chem. Soc., 20(6), 625 – 634 (2016).
S. Cheenpracha, C. Karalai, C. Ponglimanont, et al., Bioorg. Med. Chem., 14(6), 1710–1714 (2006).
K. Masawang, M. Pedro, H. Cidade, et al., Toxicol. Lett., 229(2), 393 – 401 (2014).
J. Fonseca, S. Marques, P. Silva, et al., Molecules, 21(8), 982 (2016).
M. McTigue, B. W. Murray, J. H. Chen, et al., Proc. Natl. Acad. Sci. USA, 109(45), 18281 – 18289 (2012).
C. J. Helal, Z. Kang, J. C. Lucas, et al., Bioorg. Med. Chem. Lett., 19(19), 5703 – 5707 (2009).
P. Filippakopoulos, A. Barr, O. Fedorov, et al., Structural Genomics Consortium (SGC) (2009).
T. Sander, J. Freyss, M. von Korff, et al., J. Chem. Inf. Model., 55(2), 460 – 473 (2015).
G. R. Bickerton, G. V. Paolini, J. Besnard, et al., Nature Chemistry, 4(2), 90–98 (2012).
R. Huey, G. M. Morris, S. Forli, Using AutoDock 4 and AutoDock vina with AutoDockTools: a tutorial. The Scripps
Research Institute Molecular Graphics Laboratory, 10550, 92037 (2012).
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The authors are thankful to Mahatma Gandhi University Nalgonda and Sreenidhi Institute of Science and Technology for constant encouragement in providing laboratory facilities and analytical data.
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Balaraju, V., Laxminarayana, E. & Kalyani, S. Design, Synthesis and Biological Evaluation of Amide Derivatives of Thiazolo[5,4-d]Pyrimidines as Cytotoxicity Agents for Human Cancer Cell Lines. Pharm Chem J 57, 1241–1250 (2023). https://doi.org/10.1007/s11094-024-03030-3
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DOI: https://doi.org/10.1007/s11094-024-03030-3