87235-62-9Relevant articles and documents
Combined Photoredox and Carbene Catalysis for the Synthesis of γ-Aryloxy Ketones
Wang, Pengzhi,Fitzpatrick, Keegan P.,Scheidt, Karl A.
supporting information, p. 518 - 524 (2021/12/16)
N-heterocyclic carbenes (NHCs) have emerged as catalysts for the construction of C?C bonds in the synthesis of substituted ketones under single-electron processes. Despite these recent reports, there still remains a need to increase the utility and practicality of these reactions by exploring new radical coupling partners. Herein, we report the synthesis of γ-aryloxyketones via combined NHC/photoredox catalysis. In this reaction, an α-aryloxymethyl radical is generated via oxidation of an aryloxymethyl potassium trifluoroborate salt, which is then added into styrene derivatives to provide a stabilized benzylic radical. Subsequent radical-radical coupling reaction with an azolium radical affords the γ-aryloxy ketone products. (Figure presented.).
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.
An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives
Mocci, Rita,De Luca, Lidia,Delogu, Francesco,Porcheddu, Andrea
supporting information, p. 3135 - 3144 (2016/10/09)
An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).
Efficient synthesis of primary amides from carboxylic acids using n,n'-carbonyldiimidazole and ammonium acetate in ionic liquid
Lee, Kwan Soo,Kim, Kee D.
experimental part, p. 3497 - 3500 (2011/09/30)
A novel and efficient method for the conversion of carboxylic acids to primary amides using N,N'-carbonyldiimidazole in combination with ammonium acetate/triethyl amine system in [BMIM]BF4 is developed.
Discovery of Benzamide Analogues as a Novel Class of 5-HT3 Receptor Agonists
Jorgensen, Charlotte G.,Frolund, Bente,Kehler, Jan,Jensen, Anders A.
scheme or table, p. 725 - 736 (2012/01/06)
A 5-HT3 receptor agonist based on a benzamide scaffold was identified in a screening of a small commercial compound library, and an elaborate SAR study originating from this hit was performed. The design, synthesis, and functional characterisation of benzamide analogues at the 5-HT3A receptor yielded substantial information concerning the analogues as 5-HT3 receptor agonists. However, the potencies of the derived analogues were not significantly improved over that of the initial hit. The benzamide scaffold constitutes a novel type of 5-HT3 receptor agonist, as it does not possess a positively charged functionality, which is essential for the binding of all orthosteric ligands to the receptor. Preliminary investigations suggest that the compounds may exert their effects on 5-HT3 receptors by binding to an allosteric site in the receptor complex.
Aminothiazole derivative. I. A convenient synthesis of monocyclic and condensed 5-aminothiazole derivatives
Uchikawa,Fukatsu,Aono
, p. 877 - 887 (2007/10/02)
Treatment of diamides derived from α-amino acids with phosphorus pentasulfide or Lawesson's reagent was shown to provide a convenient method to prepare 5-aminothiazoles. By this method, in addition to monocyclic 5-aminothiazoles 19, novel bicyclic 5-aminothiazole derivatives such as 4,5,6,7-tetrahydrothiazolo[5,4-b]pyridines II, 5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepines 7, 4,5,6,7,8,9-hexahydrothiazolo[5,4-b]azocine 16 and related compounds were prepared in moderate to good yields from simple diamides, suggesting the wide versatility of the method.
