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BioMed Research International
Volume 2013 (2013), Article ID 239354, 14 pages
Synthesis, Characterisation, and In Vitro Anticancer Activity of Curcumin Analogues Bearing Pyrazole/Pyrimidine Ring Targeting EGFR Tyrosine Kinase
1Department of Pharmaceutical Chemistry, Maharishi Arvind College of Pharmacy, Ambabari, Jaipur, Rajasthan 302 023, India
2Department of Pharmaceutical Chemistry, Alwar Pharmacy College, Alwar, Rajasthan 301 030, India
3Department of Pharmaceutical Chemistry, Birla Institute of Technology, Mesra, Ranchi, Jharkhand 835 215, India
Received 24 April 2013; Revised 20 July 2013; Accepted 23 July 2013
Academic Editor: Vickram Ramkumar
Copyright © 2013 Mohamed Jawed Ahsan et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- WHO, Cancer, World Health Organization, February 2006, http://en.wikipedia.org/wiki/cancer.
- M. N. Noolvi, H. M. Patel, V. Bhardwaj, and A. Chauhan, “Synthesis and in vitro antitumor activity of substituted quinazoline and quinoxaline derivatives: search for anticancer agent,” European Journal of Medicinal Chemistry, vol. 46, no. 6, pp. 2327–2346, 2011.
- N. Aydemir and R. Bilaloǧlu, “Genotoxicity of two anticancer drugs, gemcitabine and topotecan, in mouse bone marrow in vivo,” Mutation Research, vol. 537, no. 1, pp. 43–51, 2003.
- I. Bouabdallah, L. A. M'Barek, A. Zyad, A. Ramdani, I. Zidane, and A. Melhaoui, “New pyrazolic compounds as cytotoxic agents,” Natural Product Research, vol. 21, no. 4, pp. 298–302, 2007.
- D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, L. Zaprutko, A. Gzella, and R. Lesyk, “Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity,” European Journal of Medicinal Chemistry, vol. 44, no. 4, pp. 1396–1404, 2009.
- M. Shaharyar, M. M. Abdullah, M. A. Bakht, and J. Majeed, “Pyrazoline bearing benzimidazoles: search for anticancer agent,” European Journal of Medicinal Chemistry, vol. 45, no. 1, pp. 114–119, 2010.
- P.-C. Lv, H.-Q. Li, J. Sun, Y. Zhou, and H.-L. Zhu, “Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents,” Bioorganic and Medicinal Chemistry, vol. 18, no. 13, pp. 4606–4614, 2010.
- M. S. Christodoulou, S. Liekens, K. M. Kasiotis, and S. A. Haroutounian, “Novel pyrazole derivatives: synthesis and evaluation of anti-angiogenic activity,” Bioorganic and Medicinal Chemistry, vol. 18, no. 12, pp. 4338–4350, 2010.
- M. J. Ahsan, G. J. Samy, H. Khalillah, R. C. Krit, and S. Soni, “Molecular properties prediction and synthesis of novel pyrazoline carboxamide analogs as antitubercular agents,” Anti-Infective Agents, vol. 10, no. 2, pp. 117–123, 2012.
- M. J. Ahsan, J. G. Samy, H. Khalilullah, M. A. Bakht, and M. Z. Hassan, “Synthesis and antimycobacterial evaluation of 3a,4-dihydro-3H-indeno [1,2-c] pyrazole-2-carboxamide analogues,” European Journal of Medicinal Chemistry, vol. 46, no. 11, pp. 5694–5697, 2011.
- M. J. Ahsan, J. G. Samy, K. R. Dutt et al., “Design, synthesis and antimycobacterial evaluation of novel 3-substituted-N-aryl-6,7-dimethoxy-3a,4-dihydro-3H-indeno[1,2-c] pyrazole-2-carboxamide analogues,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 15, pp. 4451–4453, 2011.
- M. J. Ahsan, J. G. Samy, S. Soni et al., “Discovery of novel antitubercular 3a,4-dihydro-3H-indeno[1,2-c]pyrazole-2-carboxamide/carbothioamide analogues,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 18, pp. 5259–5261, 2011.
- M. J. Ahsan, H. Khalilullah, J. P. Stables, and J. Govindasamy, “Synthesis and anticonvulsant activity of 3a, 4-dihydro-3H-indeno[1, 2-c]pyrazole-2-carboxamide/ carbothioamide analogues,” Journal of Enzyme Inhibition & Medicinal Chemistry, vol. 28, no. 3, pp. 644–650, 2013.
- M. J. Ahsan, J. Govindasamy, H. Khalilullah et al., “POMA analyses as new efficient bioinformatics’platform to predict and optimize bioactivity of synthesized 3a, 4-dihydro-3H-indeno[1, 2-c]pyrazole-2-carboxamide/carbothioamide analogues,” Bioorganic & Medicinal Chemistry, vol. 22, no. 24, pp. 7029–7035, 2012.
- H. Khalilullah, S. Khan, M. J. Ahsan, and B. Ahmed, “Synthesis and antihepatotoxic activity of 5-(2,3-dihydro-1,4-benzodioxane-6-yl)-3-substituted-phenyl-4,5-dihydro-1H-pyrazole derivatives,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 24, pp. 7251–7254, 2011.
- M. J. Alam, M. J. Ahsan, O. Alam, and S. A. Khan, “Synthesis of 4-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(substituted phenyl)pyrimidin-2-ol analogues as 8 anti-inflammatory and analgesic agents,” Letters in Drug Design & Discovery, vol. 10, no. 8, pp. 776–782, 2013.
- D. P. Chauhan, “Chemotherapeutic potential of curcumin for colorectal cancer,” Current Pharmaceutical Design, vol. 8, no. 19, pp. 1695–1706, 2002.
- Y.-L. Jia, J. Li, Z.-H. Qin, and Z.-Q. Liang, “Autophagic and apoptotic mechanisms of curcumin-induced death in K562 cells,” Journal of Asian Natural Products Research, vol. 11, no. 11, pp. 918–928, 2009.
- A. Kunwar, A. Barik, B. Mishra, K. Rathinasamy, R. Pandey, and K. I. Priyadarsini, “Quantitative cellular uptake, localization and cytotoxicity of curcumin in normal and tumor cells,” Biochimica et Biophysica Acta, vol. 1780, no. 4, pp. 673–679, 2008.
- J. Lal, S. K. Gupta, D. Thavaselvam, and D. D. Agarwal, “Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3,4-dihydropyrimidinones of curcumin,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 8, pp. 2872–2876, 2012.
- R. K. Singh, D. Rai, D. Yadav, A. Bhargava, J. Balzarini, and E. De Clercq, “Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid,” European Journal of Medicinal Chemistry, vol. 45, no. 3, pp. 1078–1086, 2010.
- K. Saja, M. S. Babu, D. Karunagaran, and P. R. Sudhakaran, “Anti-inflammatory effect of curcumin involves downregulation of MMP-9 in blood mononuclear cells,” International Immunopharmacology, vol. 7, no. 13, pp. 1659–1667, 2007.
- S. Mishra, K. Karmodiya, N. Surolia, and A. Surolia, “Synthesis and exploration of novel curcumin analogues as anti-malarial agents,” Bioorganic and Medicinal Chemistry, vol. 16, no. 6, pp. 2894–2902, 2008.
- G. Liang, L. Shao, Y. Wang et al., “Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents,” Bioorganic and Medicinal Chemistry, vol. 17, no. 6, pp. 2623–2631, 2009.
- M. J. Ahsan, “Synthesis and anticancer activity of 3a, 4-dihydro-3H-indeno[1, 2-c]pyrazole-2-carboxamide analogues,” Letters in Drug Design & Discovery, vol. 9, no. 9, pp. 823–827, 2012.
- Salahuddin, M. Shaharyar, A. Majumdar, and M. J. Ahsan, “Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-1H-benzimidazole,” Arabian Journal of Chemistry, 2013.
- E. Zwick, J. Bange, and A. Ullrich, “Receptor tyrosine kinase signalling as a target for cancer intervention strategies,” Endocrine-Related Cancer, vol. 8, no. 3, pp. 161–173, 2001.
- H. A. Bhuva and S. G. Kini, “Synthesis, anticancer activity and docking of some substituted benzothiazoles as tyrosine kinase inhibitors,” Journal of Molecular Graphics and Modelling, vol. 29, no. 1, pp. 32–37, 2010.
- J. Mendelsohn and J. Baselga, “The EGF receptor family as targets for cancer therapy,” Oncogene, vol. 19, no. 56, pp. 6550–6565, 2000.
- M. Amir, M. J. Ahsan, and I. Ali, “Synthesis of N1-(3-chloro-4-flouropheny)-N4-substituted semicarbazones as novel anticonvulsant agents,” Indian Journal of Chemistry B, vol. 49, no. 11, pp. 1509–1514, 2010.
- A. Monks, D. Scudiero, P. Skehan et al., “Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines,” Journal of the National Cancer Institute, vol. 83, no. 11, pp. 757–766, 1991.
- M. R. Body and K. D. Paull, “Some practical considerations and applications of the national cancer institute in vitro anticancer drug discovery screen,” Drug Development Research, vol. 34, no. 2, pp. 91–109, 1995.
- R. H. Shoemaker, “The NCI60 human tumour cell line anticancer drug screen,” Nature Reviews Cancer, vol. 6, no. 10, pp. 813–823, 2006.
- M. C. Alley, D. A. Scudiero, A. Monks et al., “Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay,” Cancer Research, vol. 48, no. 3, pp. 589–601, 1988.
- M. R. Grever, S. A. Schepartz, and B. A. Chabner, “The National Cancer Institute: cancer drug discovery and development program,” Seminars in Oncology, vol. 19, no. 6, pp. 622–638, 1992.
- P. Dubreuil, S. Letard, M. Ciufolini et al., “Masitinib (AB1010), a potent and selective tyrosine kinase inhibitor targeting KIT,” PLoS ONE, vol. 4, no. 9, Article ID e7258, 2009.
- J. A. Blair, D. Rauh, C. Kung et al., “Structure-guided development of affinity probes for tyrosine kinases using chemical genetics,” Nature Chemical Biology, vol. 3, no. 4, pp. 229–238, 2007.