1312470-39-5Relevant articles and documents
Oxidative cyclizations, the synthesis of aryl-substituted c-glycosides, and the role of the second electron transfer step
Smith, Jake A.,Moeller, Kevin D.
, p. 5818 - 5821 (2013)
Anodic oxidation reactions have been used to synthesize aryl- and biaryl-substituted C-glycosides. The reactions take advantage of the tendency for alcohol nucleophiles to trap nonpolar radical cations. The addition of the alcohol to the radical cation appears to be reversible, and the success of the cyclizations is dependent on the ease with which the resulting benzylic radical is oxidized.
Synthetic Strategy for Tetraphenyl-Substituted All-E-Carotenoids with Improved Molecular Properties
Chung, Wook-Jin,Jung, Hyunuk,Koo, Sangho,Lim, Boram,Park, Myeongnam,Yang, Huijeong,Yoo, Hyebin
, (2020/03/13)
The synthetic method of tetraphenyl-substituted all-E-carotenes 1 with improved properties of antioxidant and molecular electronic conductance was developed through the formation of tetraphenyl-substituted all-E-apocarotenedial 4. The synthesis highlighted the preparation of novel subunits containing phenyl substituent(s) with E-configuration starting from the key (E)-4-chloro-2-phenylbut-2-enal (10), utilizing conjugation effect with formyl group or easy recrystallization of sulfone compounds. Sulfone-mediated coupling methods of Julia and modified Julia–Kocienski olefinations utilizing the subunits were demonstrated to produce tetraphenyl-substituted apocarotenedials 4. The major all-E-forms (73–85 % selectivity) were easily purified by SiO2 chromatography and trituration with Et2O due to the presence of the polar formyl groups. The olefination of all-E-apocarotenedials 4 and Wittig salt 5 provided all-E-9,9',13,13'-tetraphenylcarotenes 1.
Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists
Nomura, Sayaka,Endo-Umeda, Kaori,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
, p. 2347 - 2360 (2016/10/25)
Liver X receptor (LXR) agonists are candidates for the treatment of atherosclerosis via induction of ABCA1 (ATP-binding cassette A1) gene expression, which contributes to reverse cholesterol transport (RCT) and to cholesterol efflux from the liver and intestine. However, LXR agonists also induce genes involved in lipogenesis, such as SREBP-1c (sterol regulatory binding element protein 1c) and FAS (fatty acid synthase), thereby causing an undesirable increase in plasma and hepatic triglyceride (TG) levels. Recent studies indicate that LXRα contributes to lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand-binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study we identified a tetrachlorophthalimide analogue as an LXRβ-selective agonist. Structural development led to (E)-4,5,6,7-tetrachloro-2-(2-styrylphenyl)isoindoline-1,3-dione (24 a), which shows potent and selective LXRβ agonistic activity in reporter gene assays. In binding assays, compound 24 a bound to LXRβ preferentially over LXRα. It also induced the expression of ABCA1 mRNA but not SREBP-1c mRNA in cells. Compound 24 a appears to be a promising lead compound for therapeutic agents to treat atherosclerosis without the side effects induced by LXRα/β dual agonists.
Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs
Mohideen, Mazlin,Zulkepli, Suraya,Nik-Salleh, Nik-Salmah,Zulkefeli, Mohd,Weber, Jean-Frédéric Faizal Abdullah,Rahman, A. F. M. Motiur
, p. 812 - 831 (2013/07/26)
A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.
