102369-06-2Relevant articles and documents
Total syntheses of 9-epoxyfalcarindiol and its diastereomer
Zhou, Yun,Huang, Yanli,Li, Shuoning,Yang, Pengfei,Zhong, Jiangchun,Yin, Jingwei,Ji, Kaijie,Yang, Yanqing,Ye, Ning,Wang, Lifeng,Wang, Mingan,Wang, Min,Bian, Qinghua
, p. 288 - 295 (2017)
The first total syntheses of 9-epoxyfalcarindiol 1a and its diastereomer 1b have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)4.
Green asymmetric synthesis of epoxypeptidomimetics and evaluation as human cathepsin K inhibitors
Silva, Taynara L.,Vieira, Paulo C.,de Jesus, Hugo C. R.,dos Santos, Deborah A.,Br?mme, Dieter,Corrêa, Arlene G.,Fernandes, Jo?o B.,Paix?o, Marcio W.
, (2020/07/03)
Cathepsin K (CatK) is a cysteine protease known for its potent collagenolytic activity, being recognized as an important target to the development of therapies for the treatment of bone disorders. Epoxypeptidomimetics have been reported as potent inhibitors of cathepsins, thus in this work we present a green synthesis of new peptidomimetics by using a one-pot asymmetric epoxidation/Ugi multicomponent reaction. The compounds were evaluated against CatK showing selectivity when compared with cathepsin L, with an inhibition profile in the low micromolar IC50 range. Investigation of the mechanism of action carried out for compounds LSPN428 and LSPN694 suggested a mixed inhibition mode and docking studies allowed a better understanding about interactions of inhibitors with the enzyme.
Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions
Deobald, Anna Maria,Corrêa, Arlene G.,Rivera, Daniel G.,Paix?o, Márcio Weber
supporting information, p. 7681 - 7684 (2013/04/24)
An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, 'green' fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses. The Royal Society of Chemistry 2012.