631869-24-4Relevant articles and documents
Synthesis and evaluation of cyclic nitrone derivatives as potential anti-cancer agents
Zhou, Wei,Ju, Dongyan,Ao, Yuhui,Liu, Yu,Zhao, Jinbo
, p. 1309 - 1316 (2021/05/27)
Nitrones have been found to exhibit attractive biological values as immuno spin trapping agents. However, successful clinical cases of nitrone therapeutics are still lacking. Herein we report the synthesis and antiproliferative activity of a series of structurally diverse nitrone derivatives against a panel of 5 cancer cell lines, based on which indole- and pyrrole-fused were further evaluated by analogue preparation and in-vitro screening. Analogues with moderate to good potency were identified. This study shows the promise for further pursuit of nitrone-type small molecules in chemotherapy. [Figure not available: see fulltext.]
Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development
Zhang, Mengru,Liu, Shuang,Li, Hexin,Guo, Yajing,Li, Na,Guan, Meihui,Mehfooz, Haroon,Zhao, Jinbo,Zhang, Qian
supporting information, p. 12620 - 12627 (2019/09/16)
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.
One pot hydroformylation/intramolecular aldol condensation reactions of 1-allyl-2-carbonylpyrroles: A new entry into hydroindolizines synthesis
Settambolo, Roberta,Miniati, Sandra,Lazzaroni, Raffaello
, p. 2953 - 2961 (2007/10/03)
7-Formyl-5-methyl-5,6-dihydroindolizine and 7-formyl-6-methyl-5,6-dihydroindolizine were obtained via a domino hydroformylation/cyclization/dehydration reactions sequence starting from the corresponding 1-allyl-2-formylpyrroles. An intramolecular aldol condensation between the carbon atom adjacent to the formyl group in the chain of the produced aldehydes and the carbonyl group directly bonded to the pyrrole ring most likely generates the indolizine structure. 7-Formyl-6,8-dimethyl-5,6-dihydroindolizine was similarly synthesized by using 2-acetyl-1-(2-methylprop-2-enyl) pyrrole.
Organoyttrium-catalyzed sequential cyclization/silylation reactions of nitrogen-heteroaromatic dienes demonstrating 'aryl-directed' regioselectivity
Molander, Gary A.,Schmitt, Monika H.
, p. 3767 - 3770 (2007/10/03)
The reaction of 1-allyl-2-vinyl-1H-pyrroles and 1-allyl-2-vinyl-1H- indoles with arylsilanes in the presence of catalytic [Cp(TMS)2Y(μ-Me)]2 leads to highly selective cyclization/silylation events. In this process the active catalyst for the reaction, 'Cp(TMS)2YH', undergoes initial olefin insertion at the vinyl group. Even isopropenyl substituents on the heteroaromatics react in preference to less sterically encumbered allyl groups. Furthermore, the observed regioselectivity reflects an 'aryl- directed' process, whereby the more highly substituted secondary or tertiary organometallic is initially generated. This intermediate undergoes cyclization onto the remaining alkene and subsequent silylation by a σ-bond metathesis reaction, affording the observed products.
