Synthesis, characterization, and evaluation of antioxidant activity of new γ - and δ -imino esters
New Schiff bases were synthesized by condensation of methyl-5-(furan-2-yl)-5-oxopentanoate, methyl-4-(furan-2-yl)-4-oxobutanoate, methyl-5-(thiophene-2-yl)-5-oxopentanoate, and methyl-4-(thiophene-2-yl)-4-oxobutanoate with pp-anisidine and nn-butylamine. The structures of these synthesized compounds were clarified on the basis of elemental analysis, IR, 11H NMR, 1313C NMR, and GC-MS spectroscopic techniques. In addition, antioxidant activity of the synthesized compounds was evaluated on the basis of DPPH radical.
___
- Schiff, H.
Justus Liebings Ann. Chem.
1864
,
131
, 118-119.
- Eftekhari-Sis, B.; Zirak, M
. Chem. Rev.
2017
,
117
, 8326-8419.
- Balsells, J.; Mejorado, L.; Phillips, M.; Ortega, F.; Aguirre, G.; Somanathan, R. et al.
Tetrahedron-Asymmetry
1998
,
9
, 4135-4142.
- S. Krishnaraj, M.; Viswanathamurthi, P.; Sivakumar, S.
Transition Metal Chem.
2008,
33
, 643-648.
- Eswaran, S.; Adhikari, A. V.; Shetty, N. S.
Eur. J. Med. Chem
.
2009
,
44
, 4637-4647.
- Przybylski, P.; Huczynski, A.; Pyta, K.; Brzezinski, B.; Bartl, F.
Curr. Org. Chem
.
2009
,
13
, 124-148.
- Varma, M.; Pandeya, S., N.; Singh, K. N.; Stables, J. P.
Acta Pharm
.
2004
,
54
, 49-56.
- Wang, X.; Yin, J.; Shi, L.; Zhang, G. P.; Song, B.
Eur. J. Med. Chem
.
2014
,
77
, 65-74.
- Ashraf M. A.; Wajid, A.; Mahmood, K.; Maah, M. J.; Yusoff, I.
Oriental Journal of Chemistry
2011
,
27
, 363-372.
- Proetto, M.; Liu, W. K.; Hagenbach, A.; Abram, U.; Gust, R.
Eur. J. Med. Chem.
2012
,
53
, 168-175.
- Chakraborti, A. K.; Bhagat, S.; Rudrawar, S.
Tetrahedron Lett.
2004
,
45
, 7641-7644.
- Qin, W. L.; Long, S.; Panunzio, M.; Biondi, S.
Molecules
2013
,
18
, 12264-12289.
- Vazquez, M. A.; Landa, M.; Reyes, L.; Miranda, R.; Tamariz, J.; Delgado, F.
Synthetic Commun.
2004
,
34
,
2705-2718.
- Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V.; Thanusu, J.
Res. Chem. Intermediat.
2007
,
33
, 541-548.
- Law, M. C.; Cheung, T. W.; Wong, K. Y.; Chan, T. H.
J. Org. Chem.
2007
,
72
, 923-929.
- Guzen, K. P.; Guarezemini, A. S.; Orfao, A. T. G.; Cella, R.; Pereira, C. M. P; Stefani, H. A.
Tetrahedron Lett.
2007
,
48
, 1845-1848.
- Meotti, F. C.; Silva, D. O.; dos Santos, A. R. S.; Zeni, G.; Rocha, J. B. T.; Nogueira, C. W.
Environmental Toxic.
Pharm.
2003
,
37
, 37-44.
- Xue, Z. Y.; Liu, L. X.; Jiang, Y.; Yuan, W. C.; Zhang, X. M.
Eur J. Org. Chem.
2012
, 251-255.
- Cheemala, M. N.; Knochel, P.
Org. Lett.
2007
,
9
, 3089-3092.
- Malkov, A. V.; Vrankova, K.; Stoncius, S.; Kocovsky, P.
J. Org. Chem.
2009
,
74
, 5839-5849.
- Wakchaure, V. N.; Kaib, P. S. J.; Leutzsch, M.; List, B.
Angew. Chem. Int. Edit.
2015
,
54
, 11852-11856.
- Tang, Y. Z.; Liu, Z. Q.
Cell Biochem. Function.
2008
,
26
, 185-191.
- Maekawa, T.; Sakai, M.; Hiroyuki, T.; Murase, K.; Hazama, M.; Sugiyama, Y. Momose, Y.
Chem. Pharm. Bull.
2003
,
51
, 565-573.
- Breusch F. L.; Oğuzer, M.
Chem. Berichte
1954
,
87
, 1225-1228.
- Bondet, V.; Brand-Williams, W.; Berset, C.
Lebensmittel-Wissenschaft und Technologie
1997
,
30
, 609-615.