27931-91-5Relevant academic research and scientific papers
Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes
Bai, Feifei,Fang, Jianguo,Song, Zi-Long,Zhang, Baoxin
, p. 2214 - 2231 (2020/03/06)
Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.
Highly Stereoselective Total Synthesis of β-Ribofuranosylmalonate
Katagiri, Nobuya,Akatsuka, Hidenori,Haneda, Toru,Kaneko, Chikara,Sera, Akira
, p. 5464 - 5470 (2007/10/02)
β-Ribofuranosylmalonates, prospective synthons for a variety of C-nucleosides, have been synthesized stereoselectively through the high-pressure Diels-Alder reaction of furan with dialkyl (acetoxymethylene)malonate, followed by reductive retrograde aldol C-C bond fission of the diol derived from the adduct.
Method for the preparation of alkoxymethylene compounds of acetic esters and substituted acetic esters
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, (2008/06/13)
Disclosed is a method for preparation of alkoxymethylene compounds, especially methoxymethylene compounds, from substituted or unsubstituted acetic acid alkyl esters, especially methyl esters, from the corresponding hydroxymethylene compounds or their alkali salts, by reaction with excess alkanol, especially methanol, in the presence of HCl and a water-binding agent. Preferred are water-binding agents which form stable reaction products with water.
α-Alkoxyallylation of Activated Carbonyl Compounds. A Novel Variant of the Michael Reaction
Coates, Robert M.,Hobbs, Steven J.
, p. 140 - 152 (2007/10/02)
Enolic or readly enolizable carbonyl compounds undergo α-alkoxyallylation upon reaction with acetals of α,β-enals or ethoxyallene at temperatures ranging from 200 deg C to ambient.Whereas reactions of the highly enolic or acidic carbonyl compounds (endocyclic β-diketones, α-cyano ketones, α-nitro carbonyl compounds, and α-hydroxy-methylene derivatives) occurred simply upon heating, alkylation of the less acidic exocyclic β-diketones and β-keto esters was best carried out in the presence of 1 mol percent of Ni(acac)2 as a catalyst.Pyridinium p-toluenesulfonate was employed as a catalyst for alkylations with acrolein ethylene acetal.Although ethoxyallylation of acylic substrates (e.g., ethyl acetoacetate, diethyl malonate, and ethyl cyanoacetate) with acrolein diethyl acetal proved to be slow, these and related alkylations could be conviently accomplished by use of the corresponding α-hydroxymethylene derivatives.Unsaturated acetals bearing a methyl or phenyl substituent at C-2 can be employed for alkoxyallylation, but the reaction appears to be incompatible with a methyl group at C-3.The mechanism of these reactions probably involves either direct C-allylation of the carbonyl compound on the γ-position of an alkoxyallyl carbocation intermediate or an indirect pathway via O-allylation at the α-position of the carbocation followed by Claisen rearrangement.
