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This work is licensed under a Creative Commons Attribution 4.0 International License.
Silica Catalyst Promoted One-Pot Synthesis of 4-[(Dialkylamino)methyl]-1,7-diphenylhepta-1,6-diene-3,5-dione
Corresponding Author(s) : Milind B. Ubale
Asian Journal of Chemistry,
Vol. 29 No. 6 (2017): Vol 29 Issue 6
Abstract
Silica (SiO2) catalyzed one-pot synthesis of 4-[(dialkylamino)methyl]-1,7-diphenylhepta-1,6-diene-3,5-dione. An expeditious synthesis under microwave irradiation method for curcumin Mannich base derivatives are known for its biological activity. Curcumin is naturally occurring yellow pigments isolated from Curcuma longa, structurally it is polyphenolic compounds consisting spectacular biological activity. However, clinical utility of curcumin is limited due to its poor bioavailability. Present methodology offers silica catalyzed one pot, productive technique to obtain curcumin Mannich base. Both, conventional and microwave irradiation methods were found productive. The final products were characterized by 1H NMR.
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- M.G. Shioorkar and M.B. Ubale, J. Med. Chem. Drug Discov., 6, 459 (2015)
References
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D.R. Siwak, S. Shishodia, B.B. Aggarwal and R. Kurzrock, Cancer, 104, 879 (2005); https://doi.org/10.1002/cncr.21216.
T.-H. Leu and M.-C. Maa, Curr. Med. Chem. Anticancer Agents, 2, 357 (2002); https://doi.org/10.2174/1568011024606370.
P.J. Moos, K. Edes, J.E. Mullally and F.A. Fitzpatrick, Carcinogenesis, 25, 1611 (2004); https://doi.org/10.1093/carcin/bgh163.
S. Fujisawa, T. Atsumi, M. Ishihara and Y. Kadoma, Anticancer Res., 24, 563 (2004).
B.B. Aggarwal, A. Kumar and A.C. Bharti, Anticancer Res., 23, 363 (2003).
M.K. Kim, G.J. Choi and H.S. Lee, J. Agric. Food Chem., 51, 1578 (2003); https://doi.org/10.1021/jf0210369.
R.C. Reddy, P.G. Vatsala, V.G. Keshamouni, G. Padmanaban and P.N. Rangarajan, Biochem. Biophys. Res. Commun., 326, 472 (2005); https://doi.org/10.1016/j.bbrc.2004.11.051.
Y. Kiso, Y. Suzuki, N. Watanabe, Y. Oshima and H. Hikino, Planta Med., 49, 185 (1983); https://doi.org/10.1055/s-2007-969845.
N. Venkatesan, Br. J. Pharmacol., 124, 425 (1998); https://doi.org/10.1038/sj.bjp.0701877.
N. Venkatesan, D. Punithavathi and V. Arumugam, Br. J. Pharmacol., 129, 231 (2000); https://doi.org/10.1038/sj.bjp.0703067.
R. Srivastava, M. Dikshit, R.C. Srimal and B.N. Dhawan, Thromb. Res., 40, 413 (1985); https://doi.org/10.1016/0049-3848(85)90276-2.
C.D. Lao, M.T. Ruffin, D. Normolle, D.D. Heath, S.I. Murray, J.M. Bailey, M. Boggs, J. Crowell, C.L. Rock and D.E. Brenner, BMC Complem. Altern. Med., 6, 10 (2006); https://doi.org/10.1186/1472-6882-6-10.
A.L. Cheng, C.H. Hsu, J.K. Lin, M.M. Hsu, Y.F. Ho, T.S. Shen, J.Y. Ko, J.T. Lin, B. Lin, W. Ming-Shiang, H.S. Yu, G.S. Chen, T.M. Chen, C.A. Chen, M.K. Lai, Y.S. Pu, M.H. Pan, Y.J. Wang, C.C. Tsai and C.Y. Hsieh, Anticancer Res., 21(4B), 2895 (2001).
G. Shoba, D. Joy, T. Joseph, M. Majeed, R. Rajendran and P.S. Srinivas, Planta Med., 64, 353 (1998); https://doi.org/10.1055/s-2006-957450.
Z. Liu, Y. Wang, H. Zeng, W. Nie and Q. Xiang, Chin. J. Org. Chem., 34, 2345 (2014); https://doi.org/10.6023/cjoc201405024.
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E. Ferrari, F. Pignedoli, C. Imbriano, G. Marverti, V. Basile, E. Venturi and M. Saladini, J. Med. Chem., 54, 8066 (2011); https://doi.org/10.1021/jm200872q.
C. Zhao, Z. Liu and G. Liang, Curr. Pharm. Des., 19, 2114 (2013).
B. Selvkumar and R. Venkatraman, Der Pharma Chemica, 3, 84 (2011).
J.R. Fuchs, B. Pandit, D. Bhasin, J.P. Etter, N. Regan, D. Abdelhamid, C. Li, J. Lin and P. Li, Bioorg. Med. Chem. Lett., 19, 2065 (2009); https://doi.org/10.1016/j.bmcl.2009.01.104.
R. Narlawar, M. Pickhardt, S. Leuchtenberger, K. Baumann, S. Krause, T. Dyrks, S. Weggen, E. Mandelkow and B. Schmidt, ChemMedChem, 3, 165 (2008); https://doi.org/10.1002/cmdc.200700218.
D.R. Schubert, Y. Liu and T. Baiga, Methods for Treating Neural Disorders and Conditions, and Compounds Useful Therefor, US Patent 7531669, B2 (2009).
A.M. Anderson, M.S. Mitchell and R.S. Mohan, J. Chem. Educ., 77, 359 (2000); https://doi.org/10.1021/ed077p359.
S. Mishra, K. Karmodiya, N. Surolia and A. Surolia, Bioorg. Med. Chem., 16, 2894 (2008); https://doi.org/10.1016/j.bmc.2007.12.054.
M.G. Shioorkar, M.B. Ubale, S.A. Jadhav and R.K. Pardeshi, Der Chemica Sinica, 6, 110 (2015).
M.G. Shioorkar and M.B. Ubale, Der Pharma Chemica, 72, 274 (2015).
M.G. Shioorkar and M.B. Ubale, J. Med. Chem. Drug Discov., 6, 459 (2015)