TY - JOUR
T1 - Synthesis and antioxidant activity of 2-indolinone bis(Mannich bases) and related compounds
AU - Afsah, Elsayed M.
AU - Fadda, Ahmad A.
AU - Hammouda, Mohamed M.
N1 - Publisher Copyright:
© 2016, Springer-Verlag Wien.
PY - 2016/11/1
Y1 - 2016/11/1
N2 - Mannich bases attracted the interest of chemists and biologists due to their reactivity as a synthetic intermediate and their wide spectrum of biological activities. Based on the potent antioxidant, cytotoxic, and other biological properties of Mannich bases, there is a strong motivation for the continued synthesis of novel Mannich bases containing 2-indolinone core. In the present study 3-(phenacylidene)-1-(piperidin-1-ylmethyl)indolin-2-one, 3-(2-oxo-2-phenylethylidene)indolin-2-one, and 1,3-di(2-oxoindolin-3-ylidene)acetone were synthesized and used as a key intermediate in the synthesis of new 2-indolinone derivatives. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectra, and elemental analysis. The synthesized compounds were tested for their antioxidant activity in vitro using ABTS and bleomycin-dependent DNA damage assays. Graphical abstract: [Figure not available: see fulltext.]
AB - Mannich bases attracted the interest of chemists and biologists due to their reactivity as a synthetic intermediate and their wide spectrum of biological activities. Based on the potent antioxidant, cytotoxic, and other biological properties of Mannich bases, there is a strong motivation for the continued synthesis of novel Mannich bases containing 2-indolinone core. In the present study 3-(phenacylidene)-1-(piperidin-1-ylmethyl)indolin-2-one, 3-(2-oxo-2-phenylethylidene)indolin-2-one, and 1,3-di(2-oxoindolin-3-ylidene)acetone were synthesized and used as a key intermediate in the synthesis of new 2-indolinone derivatives. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectra, and elemental analysis. The synthesized compounds were tested for their antioxidant activity in vitro using ABTS and bleomycin-dependent DNA damage assays. Graphical abstract: [Figure not available: see fulltext.]
KW - 2-Indolinone derivatives
KW - Aldol reaction
KW - Antioxidant activity
KW - Bis(Mannich bases)
KW - Michael addition
KW - Phosphorus compounds
UR - http://www.scopus.com/inward/record.url?scp=84961148543&partnerID=8YFLogxK
U2 - 10.1007/s00706-016-1715-9
DO - 10.1007/s00706-016-1715-9
M3 - Article
AN - SCOPUS:84961148543
SN - 0026-9247
VL - 147
SP - 2009
EP - 2016
JO - Monatshefte fur Chemie
JF - Monatshefte fur Chemie
IS - 11
ER -