REVIEW RECENT APPROACHES FOR THE SYNTHESIS OF HYBRID RESVERATROL MOLECULES AND THEIR BIOLOGICAL ACTIVITIES: A REVIEW
- Resveratrol (RSV),
- Wittig reaction,
- aldol condensation,
- natural molecules,
- antitumor activity
- anti-Alzheimer activity ...More
Copyright (c) 2018 Journal of the Chilean Chemical Society
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
Abstract
Resveratrol (RSV) is a polyphenol produced by different plant species having a variety of biological activities. Synthesis of hybrid molecules of RSV with different natural and synthetic compounds has been studied. These hybrid molecules have been prepared by using fused or merged techniques or by using some linker groups. Wittig method was mostly applied by using the appropriate ylides to prepare the RSV core. The hybrid molecules prepared by these techniques exhibited anticancer, anti-inflammatory, antioxidant, anti-alzheimer, metal chelating and enzyme inhibitory activities. These hybrid RSV molecules can serve as a lead compounds for the future design of new drug molecules.
References
- H. Van Poppel and B. Tombal, Cancer Manag. Res. 3, 91, (2011).
- Altern. Med. Rev. 15, 152, (2010).
- N. Y. Anisimova, M. V. Kiselevsky, A. V. Sosnov, S. V. Sadovnikov, I. N. Stankov and A. A. Gakh, Chem. Cent. J. 5, 88, (2011).
- A. Koeberle and O. Werz, Drug Discovery Today 19, 1871, (2014).
- K. A. Ahmad, N. H. Harris, A. D. Johnson, H. C. Lindvall, G. Wang and K. Ahmed, Mol. Cancer Ther. 6, 1006, (2007).
- J. A. Baur and D. A. Sinclair, Nat. Rev. Drug Discov. 5, 493, (2006).
- S. Das and D. K. Das, Recent Pat. Cardiovasc. Drug Discov. 2, 133, (2007).
- M. E. Juan, I. Alfaras and J. M. Planas, Pharmacol. Res. 65, 584, (2012).
- M. Sengottuvelan, R. Senthilkumar and N. Nalini, Biochim Biophys Acta 1760, 1175, (2006).
- H. Gwak, G. Haegeman, B. K. Tsang and Y. S. Song, Mol. Carcinog. 54, 1529, (2015).
- E. Scott, W. P. Steward, A. J. Gescher and K. Brown, Mol. Nutr. Food Res. 56, 7, (2012).
- J. Tome-Carneiro, M. Larrosa, A. Gonzalez-Sarrias, F. A. Tomas- Barberan, M. T. Garcia-Conesa and J. C. Espin, Curr. Pharm. Des. 19, 6064, (2013).
- T. Walle, Ann. N.Y. Acad. Sci. 1215, 9, (2011).
- F. Belluti, G. Fontana, L. Dal Bo, N. Carenini, C. Giommarelli and F. Zunino, Bioorg. Med. Chem. 18, 3543, (2010).
- B. Meunier, Acc. Chem. Res. 41, 69, (2007).
- J. R. Morphy, Designing Multi-Target Drugs, 141, (2012).
- M. J. Matos, F. Mura, S. Vazquez-Rodriguez, F. Borges, L. Santana, E. Uriarte and C. Olea-Azar, Molecules 20, 3290, (2015).
- W. Shen, J. Mao, J. Sun, M. Sun and C. Zhang, Med. Chem. Res. 22, 1630, (2013).
- O. Gia, S. M. Magno, H. Gonzalez-Diaz, E. Quezada, L. Santana, E. Uriarte and L. Dalla Via, Biorg. Med. Chem. 13, 809, (2005).
- S. Vilar, E. Quezada, L. Santana, E. Uriarte, M. Yánez, N. Fraiz, C. Alcaide, E. Cano and F. Orallo, Bioorg. Med. Chem. Lett. 16, 257, (2006).
- X.-F. Huang, B.-F. Ruan, X.-T. Wang, C. Xu, H.-M. Ge, H.-L. Zhu and R.-X. Tan, Eur. J. Med. Chem. 42, 263, (2007).
- J. Pan, T. Xu, F. Xu, Y. Zhang, Z. Liu, W. Chen, W. Fu, Y. Dai, Y. Zhao and J. Feng, Eur. J. Med. Chem. 125, 478, (2017).
- D. Kumar, K. K. Raj, S. V. Malhotra and D. S. Rawat, MedChemComm 5, 528, (2014).
- W. Chen, X. Ge, F. Xu, Y. Zhang, Z. Liu, J. Pan, J. Song, Y. Dai, J. Zhou, J. Feng and G. Liang, Bioorg. Med. Chem. Lett. 25, 2998, (2015).
- L. Al-Riyami, M. A. Pineda, J. Rzepecka, J. K. Huggan, A. I. Khalaf, C. J. Suckling, F. J. Scott, D. T. Rodgers, M. M. Harnett and W. Harnett, J. Med. Chem. 56, 9982, (2013).
- S. Li, W. Zhang, Y. Yang, T. Ma, J. Guo, S. Wang, W. Yu and L. Kong, Eur. J. Med. Chem. 124, 1006, (2016).
- F. S. Aldawsari, O. H. Elshenawy, M. A. El Gendy, R. Aguayo-Ortiz, S. Baksh, A. O. El-Kadi and C. A. Velázquez-Martínez, J. Enzyme Inhib. Med. Chem. 30, 884, (2015).
- F. S. Aldawsari, R. Aguayo-Ortiz, K. Kapilashrami, J. Yoo, M. Luo, J. L. Medina-Franco and C. A. Velázquez-Martínez, J. Enzyme Inhib. Med. Chem. 31, 695, (2016).
- F. S. Aldawsari, R. P. Aguiar, L. A. M. Wiirzler, R. Aguayo-Ortiz, N. Aljuhani, R. K. N. Cuman, J. L. Medina-Franco, A. G. Siraki and C. A. Velázquez-Martínez, Bioorg. Med. Chem. Lett. 26, 1411, (2016).
- X. Yang, X. Qiang, Y. Li, L. Luo, R. Xu, Y. Zheng, Z. Cao, Z. Tan and Y. Deng, Bioorg. Chem. 71, 305, (2017).
- J. Yang, G. Y. Liu, D. L. Lu, F. Dai, Y. P. Qian, X. L. Jin and B. Zhou, Chemistry-A European Journal 16, 12808, (2010).
- L. A. Dutra, J. F. O. Guanaes, N. Johmann, M. E. L. Pires, C. M. Chin, S. Marcondes and J. L. Dos Santos, Bioorg. Med. Chem. Lett. 27, 2450, (2017).
- M. Murty, R. Penthala, S. Polepalli and N. Jain, Med. Chem. Res. 25, 627, (2016).
- J. Jeřábek, E. Uliassi, L. Guidotti, J. Korábečný, O. Soukup, V. Sepsova, M. Hrabinova, K. Kuča, M. Bartolini and L. E. Pena-Altamira, Eur. J. Med. Chem. 127, 250, (2017).
- F. Mao, J. Yan, J. Li, X. Jia, H. Miao, Y. Sun, L. Huang and X. Li, Org. Biomol. Chem. 12, 5936, (2014).
- C. Lu, Y. Guo, J. Yan, Z. Luo, H.-B. Luo, M. Yan, L. Huang and X. Li, J. Med. Chem. 56, 5843, (2013).
- P. Xu, M. Zhang, R. Sheng and Y. Ma, Eur. J. Med. Chem. 127, 174, (2017).
- A. Kamal, M. Ashraf, S. T. Basha, S. A. Hussaini, S. Singh, M. Vishnuvardhan, B. Kiran and B. Sridhar, Org. Biomol. Chem. 14, 1382, (2016).
- S. Park, J. K. Seok, J. Y. Kwak, Y.-H. Choi, S. S. Hong, H.-J. Suh, W. Park and Y. C. Boo, Archives of dermatological research 308, 325, (2016).
- N. A. Markina, Y. Chen and R. C. Larock, Tetrahedron 69, 2701, (2013).
- D. D. Vo and M. Elofsson, Adv. Synth. Catal. 358, 4085, (2016).