A new library of amide derivatives of thiazole-indole-isoxazoles 11a-j has been prepared and their structures were confirmed by analytical data. Further, all the compounds were preliminarily assessed for their cytotoxic activities against human cancer cell lines such as breast cancer (MCF-7), lung cancer (A549) and prostate cancer (PC3&DU-145) by using MTT assay. The results were compared with the well-recognized drug candidate, etoposide. Most of the tested compounds showed moderate cytotoxic activity. Among them, five compounds, 11a, 11b, 11c, 11g, and 11i displayed significant potential activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
P. V. Thanikachalam, R. K. Maurya, V. Garg, V. Monga, Eur. J. Med. Chem., 180, 562 – 612 (2019).
A. J. Kochanowska-Karamycan, M. T. Hamann, Chem. Rev., 110, 4489 – 4497 (2010).
A. K. Singh, V. Raj, S. Saha, Eur. J. Med. Chem., 142, 244 – 265 (2017).
M. S. Islam, A. Barakat, A. A. M. Al-Majid, et al., Bioorg. Chem., 79, 350 – 354 (2018).
B. Shu, Q. Yu, De-xuan Hu, et al., Bioorg. Med. Chem. Lett., 30, 126925 (2020).
V. T. Angelova, M. Rangelov, N. Todorova, et al., J. Bioorg. Chem., 90, 103028 (2019).
Y. Cai, N. Shao, H. Xie, et al., ACS Catal., 9, 7443 – 7448 (2019).
T. Yang,W. Moreira, S. A. Nyantakyi, et al., J. Med. Chem., 60, 2745 – 2763 (2017).
M. Demurtas, A. Baldisserotto, I. Lampronti, et al., Bioorg. Chem., 85, 568 – 576 (2019).
M. Z. Zhang, Q. Chen, G. Yang, Eur. J. Med. Chem., 89, 421 – 441 (2015).
Y. Huang, B. Zhang, J. Li, et al., Eur. J. Med. Chem., 180, 41 – 50 (2019).
S. Y. Long, C. L. Li, J. Hu, et al., Fitoterapia, 129, 145 – 149 (2018).
A. Kulkarni, I. Soni, D. S. Kelkar, et al., J. Med. Chem., 62, 6785 – 6795 (2019).
M. C. Crisanti, A. F. Wallace, V. Kapoor, et al., Mol. Cancer Ther., 8, 2221 – 2231 (2009).
X. H. Liu, Y. X. Shi, Y. Ma, et al., Eur. J. Med. Chem., 44(7), 2782 – 2786 (2009).
Y. Sawada, T. Yanai and H. Nakagawa, Pest Manage. Sci., 59(1), 49 – 57 (2003).
J. Q. Weng, D. L. Shen, C. X. Tan, et al., Chin. J. Org. Chem., 26, 1106 – 1110 (2006).
W. L. Dong, Z. X. Liu, X. H. Liu, et al., Eur. J. Med. Chem., 45, 1919 – 1926 (2010).
I. Hutchinson, M. S. Chua, H. L. Browne, et al., J. Med. Chem., 44, 1446 – 1455 (2001).
M. R. Shiradkar, K. K. Murahari, H. R. Gangadasu, et al., Bioorg. Med. Chem., 15, 3997 – 4008 (2007).
A. Kumar, C. S. Rajput, S. K. Bhati, Bioorg. Med. Chem., 15, 3089 – 3096 (2007).
A. Cohen, P. Verhaeghe, M. D. Crozet, et al., Eur. J. Med. Chem., 55, 315 – 324 (2012).
A. R. Jalilian, S. Sattari, M. Bineshmarvasti, et al., Arch. Pharm. Med. Chem., 333, 347 – 354 (2000).
A. S. Mayhoub, M. Khaliq, C. Botting, Bioorg. Med. Chem., 19, 3845 – 3854 (2011).
M. H. Shih, K. F. Ying, Bioorg. Med. Chem., 12, 4633 – 4643 (2004).
K. M. Dawood, H. A. Gawad, E. A. Rageb, et al., Bioorg. Med. Chem., 14, 3672 – 3680 (2006).
P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti, Bioorg. Med. Chem., 14, 3859 – 3864 (2006).
C. L. Liu, L. Li, Z. M. Li, Bioorg. Med. Chem., 12, 2825 – 2830 (2004).
E. Abruzzese, M. Breccia, R. Latagliata, Bio. Drugs, 28, 17 – 26 (2014).
Ch. Karuna, Ch. Venkata Ramana Reddy, E. Laxminarayana, Chem. Data Collection, 41, 100925 (2022).
Acknowledgments
The authors are thankful to DST, India fellowship to the first author and J N T University Hyderabad for providing the necessary facilities to carry out this work.
Conflict of Interest
The authors declare that they have no competing interests.
Funding
No funding has been received from any source.
Animal/human consent (for any medical/life science journals)
Not applicable
Grant Support
Not applicable
Author Contributions
Karuna carried out the research work, Venkata Ramana Reddy prepared the manuscript. Laxminarayana performed statistical analysis. All authors approved the manuscript.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Karuna, C., Reddy, C.R. & Laxminarayana, E. Design, Synthesis and Biological Evaluation of Amide Derivatives of Thiazole-Indole-Isoxazoles as Anticancer Agents. Pharm Chem J 57, 1732–1737 (2024). https://doi.org/10.1007/s11094-024-03073-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11094-024-03073-6