Synthesis and electronic properties of alkyl- and alkyloxy-curcuminoids

Tahseen Abed Al Qader Alsalim; Bahjat Ali Saeed; Rita Sabah Elias; Hanna Sabeeh Abbo; Salam Jaber Titinchi

doi:10.5155/eurjchem.4.1.70-73.728

PDF

Published: Mar 31, 2013

DOI: https://doi.org/10.5155/eurjchem.4.1.70-73.728

Keywords:

Turmeric, Tautomerism, Curcuminoids, Electronic transitions, Alkyloxy-curcuminoids, High resolution mass spectra

Section

Research Article

Issue

Vol. 4 No. 1 (2013): March 2013

Dates

Received 2012-12-30
Accepted 2013-02-02
Published 2013-03-31

Tahseen Abed Al Qader Alsalim

Department of Chemistry, College of Education, University of Basrah, Basrah-16001, Iraq

Bahjat Ali Saeed

Department of Chemistry, College of Education, University of Basrah, Basrah-16001, Iraq

Rita Sabah Elias

Department of Pharmaceutical Chemistry, College of Pharmacy, University of Basrah-16001, Basrah, Iraq

Hanna Sabeeh Abbo

Department of Chemistry, University of the Western Cape, Bellville, Cape Town 7535, South Africa

Salam Jaber Titinchi

Department of Chemistry, University of the Western Cape, Bellville, Cape Town 7535, South Africa

Abstract

Two series of p-alkyl- and p-alkoxy-substituted curcuminoids were synthesized. The validity of the proposed structures was checked on the basis of their high resolution mass spectra as well as NMR, IR and electronic spectra. The spectra were essentially similar for both series. NMR, IR and electronic spectra showed that the compounds exist mainly or exclusively as the enolic tautomer in their solutions. Theoretical study for the electronic spectra was conducted to account for the origins of the electronic transitions that are responsible for the UV-VIS bands. The theoretical calculations were done at the B3LYP/6-31G(d) level of theory and predicted that the similarity of the electronic spectra is may be due to the close resemblance of their molecular orbitals.

This Abstract was viewed 1936 times |

Article PDF downloaded 1926 times

How to Cite

(1)

Alsalim, T. A. A. Q.; Saeed, B. A.; Elias, R. S.; Abbo, H. S.; Titinchi, S. J. Synthesis and Electronic Properties of Alkyl- and Alkyloxy-Curcuminoids. Eur. J. Chem. 2013, 4, 70-73.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Anand, P.; Thomas, S. G.; Kunumakkara, A. B.; Sundaram, C.; Harikumar, K. B.; Sung, B.; Tharakan, S. T.; Misra, K.; Priyadarsini, I. K.; Rajasekharan, K. N.; Aggarwal, B. B. Biochem. Pharmacol. 2008, 76, 1590-1611.
http://dx.doi.org/10.1016/j.bcp.2008.08.008
PMid:18775680

[2]. Lagisetty, P.; Powell, D. R.; Awasthi, V. J. Mol. Struct. 2009, 936, 23-28.
http://dx.doi.org/10.1016/j.molstruc.2009.07.016

[3]. Tonnesen, H. H.; Karlsen, J.; Mostad, A. Acta Chem. Scand. B 1982, 36, 475-479.
http://dx.doi.org/10.3891/acta.chem.scand.36b-0475

[4]. Parimita, S. P.; Ramshankar, Y. V.; Suresh, S.; Row, T. N. G. Acta Cryst. E 2007, 63, 860-862.
http://dx.doi.org/10.1107/S160053680700222X

[5]. Ishigami, Y.; Goto, M.; Masuda, T.; Suzuki, S. J. Jpn. Soc. Colour Mater. 1999, 72, 71-77.

[6]. Pyton, F.; Sandusky, P.; Alworth, W. L. J. Natural Prod. 2007, 70, 143-146.
http://dx.doi.org/10.1021/np060263s
PMid:17315954

[7]. Balasubramanian, K. J. Agric. Food Chem. 2006, 54, 3512-3520.
http://dx.doi.org/10.1021/jf0603533

[8]. Shen, L.; Zhang, H-Y.; Ji, H-F. Org. Lett. 2005, 7, 243-246.
http://dx.doi.org/10.1021/ol047766e
PMid:15646968

[9]. Kong, L.; Priadarsini, K. I.; Zhang, H-Y. Theochem. 2005, 684, 111-116.
http://dx.doi.org/10.1016/j.theochem.2004.06.034

[10]. Benassi, R.; Ferrari, E.; Lazzari, S.; Spagnolo, F.; Saladini, M. J. Mol. Str. 2008, 892, 168-176.
http://dx.doi.org/10.1016/j.molstruc.2008.05.024

[11]. Amolins, M. W.; Peterson, L. B.; Blagg, B. S. Bioorg. Med. Chem. 2009, 17, 360-367.
http://dx.doi.org/10.1016/j.bmc.2008.10.057
PMid:19019687 PMCid:2753864

[12]. Ahn, C. M.; Park, B-G.; Wooa, H. B.; Hamc, J.; Shin, W-S., Lee, S. Bioorg. Med. Chem. 2009, 19, 1481-1483.
http://dx.doi.org/10.1016/j.bmcl.2009.01.019
PMid:19179077

[13]. Ke, D.; Wang, X.; Yang, Q.; Niu, Y.; Chai, S.; Chen, Z.; An, X.; Shen, W. Langmuir 2011, 27, 14112-14117.
http://dx.doi.org/10.1021/la203592j
PMid:22004075

[14]. Adhikary, R.; Barnes, C. A.; Trampel, R. L.; Wallace, S. J.; Kee, T. W.; Petrich, J. W. J. Phys. Chem. 2011, 115, 10707-10714.

[15]. Shao, W-Y.; Cao, W-N.; Yu, Z-W.; Pan, W-J.; Qiu, X.; Bu, X-Z.; An, L-K.; Huang, Z-H.; Gu, L-Q.; Chan, A. S. C. Tetrahedron Lett. 2006, 47, 4085-4089.
http://dx.doi.org/10.1016/j.tetlet.2006.03.145

[16]. Qiu, X.; Liu, Z.; Shaw, W-I.; Liu, X.; Jing, D-B.; Yu, Y-J.; An, L-K.; Huang, S-L.; Bu, X-Z.; Huang, Z-S; Gu, L-Q. Bioorg. Med. Chem. 2008, 16, 8035-8041.
http://dx.doi.org/10.1016/j.bmc.2008.07.054
PMid:18678491

[17]. Fuchs, J. R.; Pandit, B.; Bhasin, D.; Etter, J. P.; Regan, N.; Abdelhamid, D.; Li, C.; Lin, J.; Li, P-K. Bioorg. Med. Chem. Lett. 2009, 19, 2065-2069.
http://dx.doi.org/10.1016/j.bmcl.2009.01.104
PMid:19249204

[18]. Ferrari, E.; Lazzari, S.; Marverti, G.; Pignedoli, F.; Saladini, F. Bioorg. Med. Chem. 2009, 17, 3043-3052.
http://dx.doi.org/10.1016/j.bmc.2009.03.016
PMid:19329324

[19]. Granovsky, A. A. Firefly version 7.1.G, http://classic.chem.msu/gran/firefly/index.html

[20]. Scmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Albert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
http://dx.doi.org/10.1002/jcc.540141112

Supporting Agencies

Most read articles by the same author(s)

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics