18315-80-5Relevant articles and documents
Addition of thionucleophiles to nitrocinnamates: Approach toward synthesis of (alkyl/aryl)thio-amino acids
Lewandowska, Elzbieta
, p. 123 - 133 (2016)
The addition of alkyl or aryl thiols to α-nitro or β-nitrocinnamate in the presence of base provided Michael addition products. In the case of β-nitro compounds reaction occurred via the formation of anti-Michael adducts. Selective nitro reduction of α-ni
Design, synthesis, and evaluation of a novel macrocyclic anti-EV71 agent
Li, Peng,Wu, Siqi,Xiao, Tianyichen,Li, Yunlong,Su, Zhiming,Wei, Wei,Hao, Fei,Hu, Guoping,Lin, Fusen,Chen, Xinsheng,Gu, Zhengxian,Lin, Tianwei,He, Haiying,Li, Jian,Chen, Shuhui
, (2020/05/18)
We describe here the design, synthesis, and evaluation of a macrocyclic peptidomimetic as a potent agent targeting enterovirus A71 (EV71). The compound has a 15-membered macrocyclic ring in a defined conformation. Yamaguchi esterification reaction was used to close the 15-membered macrocycle instead of the typical Ru-catalyzed ring-closing olefin metathesis reaction. The crystallographic characterization of the complex between this compound and its target, 3C protease from EV71, validated the design and paved the way for the generation of a new series of anti-EV71 agents.
Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions
Gagnot, Glwadys,Hervin, Vincent,Coutant, Eloi P.,Desmons, Sarah,Baatallah, Racha,Monnot, Victor,Janin, Yves L.
, p. 2846 - 2852 (2018/11/27)
We report here on the use of ethyl nitroacetate as a glycine template to produce α-amino esters. This started with a study of its condensation with various arylacetals to give ethyl 3-aryl-2-nitroacrylates followed by a reduction (NaBH4 and then zinc/HCl) into α-amino esters. The scope of this method was explored as well as an alternative with arylacylals instead. We also focused on various [2 + 3] cycloadditions, one leading to a spiroacetal, which led to the undesired ethyl 5-(benzamidomethyl)isoxazole-3-carboxylate. The addition of ethyl nitroacetate on a 5-methylene-4,5-dihydrooxazole using cerium(IV) ammonium nitrate was also explored and the synthesis of other oxazole-bearing α-amino esters was achieved using gold(I) chemistry.
