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Journal of Chemistry
Volume 2017, Article ID 6436185, 6 pages
https://doi.org/10.1155/2017/6436185
Research Article

A Novel Green Synthesis of Thalidomide and Analogs

1Department of Chemistry, Stockton University, 101 Vera King Farris Drive, Galloway, NJ 08205-9441, USA
2Department of Chemistry and Earth Sciences, Qatar University, P.O. Box 2713, Doha, Qatar

Correspondence should be addressed to Yousef M. Hijji; aq.ude.uq@ijjih.fesuoy

Received 13 November 2016; Accepted 18 January 2017; Published 20 February 2017

Academic Editor: José L. Arias Mediano

Copyright © 2017 Ellis Benjamin and Yousef M. Hijji. 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.

Linked References

  1. R. Talaat, W. El-Sayed, H. S. Agwa, A. M. Gamal-Eldeen, S. Moawia, and M. A. H. Zahran, “Anti-inflammatory effect of thalidomide dithiocarbamate and dithioate analogs,” Chemico-Biological Interactions, vol. 238, pp. 74–81, 2015. View at Publisher · View at Google Scholar · View at Scopus
  2. M. Y. Kim, R. Sposto, A. Swaika et al., “Pharmacoeconomic implications of lenalidomide maintenance therapy in multiple myeloma,” Oncology, vol. 87, no. 4, pp. 224–231, 2014. View at Publisher · View at Google Scholar · View at Scopus
  3. Y. Liu, X. Huang, X. He et al., “A novel effect of thalidomide and its analogs: suppression of cereblon ubiquitination enhances ubiquitin ligase function,” The FASEB Journal, vol. 29, no. 12, pp. 4829–4839, 2015. View at Publisher · View at Google Scholar · View at Scopus
  4. L. Roziaková, M. Mistrík, and A. Bátorová, “Pomalidomide in the treatment of relapsed and refractory multiple myeloma,” Klinicka Onkologie, vol. 27, no. 5, pp. 318–325, 2014. View at Publisher · View at Google Scholar · View at Scopus
  5. G. Fouquet, C. Bories, S. Guidez et al., “Pomalidomide for multiple myeloma,” Expert Review of Hematology, vol. 7, no. 6, pp. 719–731, 2014. View at Publisher · View at Google Scholar · View at Scopus
  6. C. Yang, P. Singh, H. Singh, M.-L. Le, and W. El-Matary, “Systematic review: thalidomide and thalidomide analogues for treatment of inflammatory bowel disease,” Alimentary Pharmacology & Therapeutics, vol. 41, no. 11, pp. 1079–1093, 2015. View at Publisher · View at Google Scholar · View at Scopus
  7. S. Harbour and N. Brown, “Thalidomide improves clinical remission in children with Crohn's disease,” Archives of Disease in Childhood, vol. 100, no. 2, article 111, 2015. View at Publisher · View at Google Scholar · View at Scopus
  8. S. C. Ng, “Thalidomide and refractory crohn's disease: what is in the future?” Journal of Clinical Gastroenterology, vol. 48, no. 6, pp. 476–477, 2014. View at Publisher · View at Google Scholar · View at Scopus
  9. S. Kamath, S. A. Vaccaro, T. H. Rea, and M. T. Ochoa, “Recognizing and managing the immunologic reactions in leprosy,” Journal of the American Academy of Dermatology, vol. 71, no. 4, pp. 795–803, 2014. View at Publisher · View at Google Scholar · View at Scopus
  10. S. Zhou, F. Wang, T.-C. Hsieh, J. M. Wu, and E. Wu, “Thalidomide—a notorious sedative to a wonder anticancer drug,” Current Medicinal Chemistry, vol. 20, no. 33, pp. 4102–4108, 2013. View at Publisher · View at Google Scholar · View at Scopus
  11. C. Mahony, L. Erskine, J. Niven, N. H. Greig, W. D. Figg, and N. Vargesson, “Pomalidomide is nonteratogenic in chicken and zebrafish embryos and nonneurotoxic in vitro,” Proceedings of the National Academy of Sciences of the United States of America, vol. 110, no. 31, pp. 12703–12708, 2013. View at Publisher · View at Google Scholar · View at Scopus
  12. M. Alsina, P. S. Becker, X. Zhong et al., “Lenalidomide maintenance for high-risk multiple myeloma after allogeneic hematopoietic cell transplantation,” Biology of Blood and Marrow Transplantation, vol. 20, no. 8, pp. 1183–1189, 2014. View at Publisher · View at Google Scholar · View at Scopus
  13. L. St John, S. M. Gordon, R. Childs et al., “Topical thalidomide gel in oral chronic GVHD and role of in situ cytokine expression in monitoring biological activity,” Bone Marrow Transplantation, vol. 48, no. 4, pp. 610–611, 2013. View at Publisher · View at Google Scholar · View at Scopus
  14. P. J. Martin, Y. Inamoto, P. A. Carpenter, S. J. Lee, and M. E. D. Flowers, “Treatment of chronic graft-versus-host disease: past, present and future,” Korean Journal of Hematology, vol. 46, no. 3, pp. 153–163, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. L. Song, X. Zhou, and X. Li, “Phase II trial of granulocyte-macrophage colony-stimulating factor plus thalidomide in older patients with castration-resistant prostate cancer,” Molecular and Clinical Oncology, vol. 3, no. 4, pp. 865–868, 2015. View at Publisher · View at Google Scholar
  16. Z. Qiao, J. Yuan, J. Shen et al., “Effect of thalidomide in combination with gemcitabine on human pancreatic carcinoma SW-1990 cell lines in vitro and in vivo,” Oncology Letters, vol. 9, no. 5, pp. 2353–2360, 2015. View at Publisher · View at Google Scholar · View at Scopus
  17. P. M. Da Costa, M. P. Da Costa, A. A. Carvalho et al., “Improvement of in vivo anticancer and antiangiogenic potential of thalidomide derivatives,” Chemico-Biological Interactions, vol. 239, article no. 7412, pp. 174–183, 2015. View at Publisher · View at Google Scholar · View at Scopus
  18. L. C. D. Coêlho, M. V. De Oliveira Cardoso, D. R. M. Moreira et al., “Novel phthalimide derivatives with TNF-α and IL-1β expression inhibitory and apoptotic inducing properties,” MedChemComm, vol. 5, no. 6, pp. 758–765, 2014. View at Publisher · View at Google Scholar · View at Scopus
  19. M. V. De Oliveira Cardoso, D. R. Magalhães Moreira, G. B. Oliveira Filho et al., “Design, synthesis and structure—activity relationship of phthalimides endowed with dual antiproliferative and immunomodulatory activities,” European Journal of Medicinal Chemistry, vol. 96, pp. 491–503, 2015. View at Publisher · View at Google Scholar · View at Scopus
  20. A. Diamanti, T. Capriati, B. Papadatou et al., “The clinical implications of thalidomide in inflammatory bowel diseases,” Expert Review of Clinical Immunology, vol. 11, no. 6, pp. 699–708, 2015. View at Publisher · View at Google Scholar · View at Scopus
  21. Y. Huang, Y. Zang, L. Zhou, W. Gui, X. Liu, and Y. Zhong, “The role of TNF-α/NF-κB pathway on the up-regulation of voltage-gated sodium channel Nav1.7 in DRG neurons of rats with diabetic neuropathy,” Neurochemistry International, vol. 75, pp. 112–119, 2014. View at Publisher · View at Google Scholar · View at Scopus
  22. M. S. Ali, R. M. Starke, P. M. Jabbour et al., “TNF-α induces phenotypic modulation in cerebral vascular smooth muscle cells: implications for cerebral aneurysm pathology,” Journal of Cerebral Blood Flow and Metabolism, vol. 33, no. 10, pp. 1564–1573, 2013. View at Publisher · View at Google Scholar · View at Scopus
  23. A. Vangsted, T. W. Klausen, and U. Vogel, “Genetic variations in multiple myeloma II: association with effect of treatment,” European Journal of Haematology, vol. 88, no. 2, pp. 93–117, 2012. View at Publisher · View at Google Scholar · View at Scopus
  24. L. Mazzoccoli, S. H. Cadoso, G. W. Amarante et al., “Novel thalidomide analogues from diamines inhibit pro-inflammatory cytokine production and CD80 expression while enhancing IL-10,” Biomedicine & Pharmacotherapy, vol. 66, no. 5, pp. 323–329, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. M. Çizmecioğlu, V. Pabuççuoğlu, P. Ballar, A. Pabuççuoğlu, and Z. Soyer, “Synthesis and screening of cyclooxygenase inhibitory activity of some 1,3-dioxoisoindoline derivatives,” Arzneimittel-Forschung/Drug Research, vol. 61, no. 3, pp. 186–190, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. G. D. Ferguson, K. Jensen-Pergakes, C. Wilkey et al., “Immunomodulatory drug CC-4047 is a cell-type and stimulus-selective transcriptional inhibitor of cyclooxygenase 2,” Journal of Clinical Immunology, vol. 27, no. 2, pp. 210–220, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. J. L. Masferrer, “Methods of using a combination of cyclooxygenase-2 selective inhibitors and thalidomide for the treatment of neoplasia,” US20030013739A1, 2003.
  28. E. D. Q. Crusoe, F. Higashi, M. P. N. C. Padilha et al., “Outcomes of autologous transplantation for multiple myeloma according to different induction regimens,” Revista Brasileira de Hematologia e Hemoterapia, vol. 36, no. 1, pp. 19–24, 2014. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Bolzoni, P. Storti, S. Bonomini et al., “Immunomodulatory drugs lenalidomide and pomalidomide inhibit multiple myeloma-induced osteoclast formation and the RANKL/OPG ratio in the myeloma microenvironment targeting the expression of adhesion molecules,” Experimental Hematology, vol. 41, no. 4, pp. 387.e1–397.e1, 2013. View at Publisher · View at Google Scholar · View at Scopus
  30. M. Lazarini, F. Traina, S. M. Winnischofer, F. F. Costa, M. L. S. Queiroz, and S. T. O. Saad, “Effects of thalidomide on long-term bone marrow cultures from patients with myelodysplastic syndromes: induction of IL-10 expression in the stromal layers,” Leukemia Research, vol. 35, no. 8, pp. 1102–1107, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. E. Shannon, R. Noveck, F. Sandoval, and B. Kamath, “Thalidomide suppressed IL-1β while enhancing TNF-α and IL-10, when cells in whole blood were stimulated with lipopolysaccharide,” Immunopharmacology and Immunotoxicology, vol. 30, no. 3, pp. 447–457, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. J. Chen, K. Natte, A. Spannenberg, H. Neumann, M. Beller, and X.-F. Wu, “Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide,” Organic and Biomolecular Chemistry, vol. 12, no. 30, pp. 5578–5581, 2014. View at Publisher · View at Google Scholar · View at Scopus
  33. Z. Xiao, K. Schaefer, S. Firestine, and P.-K. Li, “Solid-phase synthesis of thalidomide and its analogues,” Journal of Combinatorial Chemistry, vol. 4, no. 2, pp. 149–153, 2002. View at Publisher · View at Google Scholar · View at Scopus
  34. B. Satyanarayana, P. Murali Krishna, and D. Ramachndran, “A novel and efficient synthesis of thalidomide,” International Journal of ChemTech Research, vol. 3, no. 1, pp. 234–237, 2011. View at Google Scholar · View at Scopus
  35. N. Shibata, T. Yamamoto, and T. Toru, “Synthesis of 2-(2, 6-dioxo-3-piperidinyl)-1h-isoindole-1, 3(2h)-dione (thalidomide),” in Topics in Heterocyclic Chemistry, vol. 8, pp. 73–97, Springer, Berlin, Germany, 2007. View at Google Scholar
  36. X.-H. Yuan, H.-Q. Guo, X.-P. Qiu, C.-Q. Kang, X.-D. Liu, and L.-X. Gao, “One-step synthesis of thalidomide and its important derivatives,” Chemical Journal of Chinese Universities, vol. 26, no. 8, pp. 1477–1479, 2005. View at Google Scholar · View at Scopus
  37. M.-Y. Chang, C.-H. Chang, S.-T. Chen, and N.-C. Chang, “A synthesis of thalidomide,” Journal of the Chinese Chemical Society, vol. 49, no. 3, pp. 383–385, 2002. View at Publisher · View at Google Scholar · View at Scopus
  38. G. W. Muller, W. E. Konnecke, A. M. Smith, and V. D. Khetani, “A concise two-step synthesis of thalidomide,” Organic Process Research & Development, vol. 3, no. 2, pp. 139–140, 1999. View at Publisher · View at Google Scholar · View at Scopus
  39. F. A. Luzzio, D. Y. Duveau, and W. D. Figg, “A chiral pool approach toward the synthesis of thalidomide metabolites,” Heterocycles, vol. 70, pp. 321–334, 2006. View at Publisher · View at Google Scholar · View at Scopus
  40. H. B. Casazza Fanchini and A. Rodriguez Welton, “Novel process for the synthesis of thalidomide,” MX2006008774A, 2008.
  41. M. Alpegiani, A. Mazzoni, D. Vergani, and W. Cabri, “Process for the one-pot synthesis of thalidomide directly from glutamine using phthaloylating agents and condensing agents,” EP1602654A1, 2005.
  42. R. Varala and S. R. Adapa, “A practical and efficient synthesis of thalidomide via Na/liquid NH3 methodology,” Organic Process Research and Development, vol. 9, no. 6, pp. 853–856, 2005. View at Publisher · View at Google Scholar · View at Scopus
  43. N. Flaih, C. Pham-Huy, and H. Galons, “An expeditious synthesis of cyclic imides. Tetrahedron Lett. Tetrahedron,” Asymmetry, vol. 6, pp. 3697–3698, 1999. View at Google Scholar
  44. J. A. Seijas, M. P. Vazquez-Tato, C. Gonzalez-Bande, M. M. Martinez, and B. Pacios-Lopez, “Microwave promoted synthesis of a rehabilitated drug: thalidomide,” Synthesis, vol. 2001, no. 7, pp. 999–1000, 2001. View at Publisher · View at Google Scholar
  45. S. You, Y. Li, D. Chen et al., “Application of microwave-assisted method in synthesis of thalidomide,” Huaxue Yanjiu Yu Yingyong, vol. 23, pp. 652–656, 2011. View at Google Scholar
  46. J. Guo, Y. Zheng, D. Guo et al., “Application of the microwave-assisted method in synthesis of thalidomide amino acid derivatives,” Huaxue Yanjiu Yu Yingyong, vol. 21, pp. 582–586, 2009. View at Google Scholar
  47. Y. M. Hijji and E. Benjamin, “Efficient microwave assisted syntheses of unsubstituted cyclic imides,” Heterocycles, vol. 68, no. 11, pp. 2259–2267, 2006. View at Publisher · View at Google Scholar · View at Scopus
  48. E. Benjamin and Y. Hijji, “The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation,” Molecules, vol. 13, no. 1, pp. 157–169, 2008. View at Publisher · View at Google Scholar · View at Scopus
  49. Y. M. Hijji, E. Benjamin, E. Benjamin, R. J. Butcher, and J. P. Jasinski, “3-(2,6-dioxopiperidin-3-yl)-3-aza-bicyclo-[3.2.0]heptane-2,4-dione,” Acta Crystallographica, vol. 65, pp. 394–395, 2009. View at Google Scholar