88184-83-2Relevant academic research and scientific papers
l-Proline catalyzed condensation of salicylaldehydes with ethyl nitroacetate: an efficient access to 3-nitrocoumarins
Sharma, Rajesh Kumar,Priyanka,Katiyar, Diksha
, p. 2157 - 2161 (2016)
Abstract: l-Proline catalyzed condensation of salicylaldehydes and ethyl nitroacetate afforded 3-nitrocoumarins in good to high yields under mild conditions. This organocatalyzed process offers a much improved yield of 3-nitrocoumarins and well tolerates both electron-donating and electron-withdrawing substituents on the phenyl ring. Graphical abstract: [Figure not available: see fulltext.]
Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D
Manjappa, Kiran B.,Lin, Jhih-Min,Yang, Ding-Yah
, p. 7648 - 7656 (2017/07/26)
An efficient construction of phenyl-substituted coumarin-pyrrole-isoquinoline-fused pentacycle via base-promoted Grob-type coupling of 3-nitrocoumarin and papaverine in a sealed tube is reported. This reaction is further applied to the total synthesis of lamellarin H in three linear steps and lamellarin D in eight linear steps with overall yields of 31% and 14%, respectively.
Tyrosine-like condensed derivatives as tyrosinase inhibitors
Matos, Maria Joao,Santana, Lourdes,Uriarte, Eugenio,Serra, Silvia,Corda, Marcella,Fadda, Maria Benedetta,Era, Benedetta,Fais, Antonella
experimental part, p. 742 - 746 (2012/07/14)
Objectives We report the pharmacological evaluation of a new series of 3-aminocoumarins differently substituted with hydroxyl groups, which have been synthesized because they include in their structures the tyrosine fragment (tyrosine-like compounds), with the aim of discovering structural features necessary for tyrosinase inhibitory activity. Methods The synthesized compounds 4 and 7-9 were evaluated in vitro as mushroom tyrosinase inhibitors. Key findings Two of the described compounds showed lower IC50 (concentration giving 50% inhibition of tyrosinase activity) than umbelliferone, used as a reference compound. Conclusions Compound 7 (IC50 = 53 μm) was the best tyrosinase inhibitor of this small series, having an IC50 value 10-fold lower than umbelliferone. Compound 7 (3-amino-7-hydroxycoumarin) had amino and hydroxyl groups precisely mimicking the same positions that both groups occupy on the tyrosine molecule. 2012 The Authors. JPP
Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes
Versleijen, Jos P. G.,Van Leusen, Albert M.,Feringa, Ben L.
, p. 5803 - 5806 (2007/10/03)
The asymmetric copper(I) phosphoramidite catalyzed conjugate addition of dialkylzinc reagents to E,Z-mixtures of α,β-unsaturated nitroacetates provided the 1,4-adducts in excellent yields but with low e.e.'s. High enantioselectivities (e.e.'s up to 92%) w
