Abstract
Multi-substituted benzylidenethiazolidine-2,4-diones 3a-h were synthesized by Knoevenagel condensation of di- or tri-substituted 4-hydroxybenzaldehydes [or 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone] 1 with thiazolidine-2,4-dione (2) and evaluated for antioxidant activities of Cu(2+)-induced oxidation of human low-density lipoproteins (LDL). Among compounds 3a-h, 3a was superior to probucol in LDL-antioxidant activities and found to be ninefold more active than probucol. Due to its potency, compound 3a was tested for complementary in vitro investigations, such as TBARS assay (IC(50) = 0.1 microM), lag time (240 min at 1.5 microM), relative electrophoretic mobility (REM) of ox-LDL (inhibition of 83% at 10 microM), fragmentation of apoB-100 (inhibition of 61% at 5 microM), and radical DPPH scavenging activity on copper-mediated LDL oxidation. In macrophage-mediated LDL oxidation, the TBARS formation was also inhibited by compound 3a.
Citations
Apr 7, 2006·Archives of Pharmacal Research·Kyung-Ran ImDae Keun Kim
Dec 20, 2007·Archives of Pharmacal Research·Myoung-Chong SongNam-In Baek
Apr 12, 2007·Archives of Pharmacal Research·WenYi JinKiHwan Bae
Jun 25, 2005·Archives of Pharmacal Research·Dong-Hyun KimNam-In Baek
May 16, 2008·Archives of Pharmacal Research·Myoung-Chong SongNam-In Baek
Dec 4, 2013·Archives of Pharmacal Research·Hee-Jung ParkNam-In Baek
Sep 26, 2012·Journal of Medicinal Chemistry·Venkata Ramana SirivoluZhengqiang Wang
Aug 8, 2008·Bioscience, Biotechnology, and Biochemistry·Tran Minh NgocByung-Sun Min
Jun 22, 2011·Experimental & Molecular Medicine·Jae-Hoon ChoiGoo Taeg Oh
Jan 1, 2013·International Journal of Medicinal Chemistry·Ravinder Singh BhattiJagir S Sandhu
Mar 25, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Raied M ShakirMahmood Ameen Abdulla
Nov 25, 2005·Drug Development and Industrial Pharmacy·M L N DubuissonJ Marchand-Brynaert
Aug 6, 2010·Atherosclerosis·Jae-Hoon ChoiGoo Taeg Oh
Nov 13, 2007·Journal of Food Science·B J XuS K C Chang
Jul 1, 2006·Journal of Ethnopharmacology·Tran Manh HungKiHwan Bae
Jan 14, 2012·Free Radical Research·Anup SrivastavaT Shivanandappa
Jun 3, 2005·Biological & Pharmaceutical Bulletin·Phuong Thien ThuongKiHwan Bae
Sep 2, 2009·Biological & Pharmaceutical Bulletin·Phuong Thien ThuongKeon Wook Kang
Apr 4, 2019·Artificial Cells, Nanomedicine, and Biotechnology·Seyyed Mojtaba MousaviAli Mohammad Amani
Dec 27, 2011·Molecular and Cellular Biochemistry·Anup SrivastavaT Shivanandappa
May 17, 2019·Mini Reviews in Medicinal Chemistry·Harsh KumarRakesh Kumar Marwaha
Feb 2, 2006·Journal of Agricultural and Food Chemistry·Anup SrivastavaT Shivanandappa
Sep 22, 2021·The Journal of Organic Chemistry·Amani ToumiMichael Knorr
Feb 20, 2007·Journal of Agricultural and Food Chemistry·Chunhua WeiDai-Eun Sok