title: Regio- and diastereoselective construction of α-hydroxy-δ-amino ester derivatives via 1,4-conjugate addition of β,γ-unsaturated N-sulfonylimines.
abstract: A first example of 1,4-conjugate addition of β,γ-unsaturated N-sulfonylimines via the oxonium ylides trapping process was developed. This method afforded a novel and efficient access for the high regio- and diastereoselective construction of α-hydroxyl-δ-amino esters derivatives, which exhibit inhibitory activity on PTP1B and SIRT1 enzymes in vitro. The synthetic potentials and the biological activity of the resulting products were well demonstrated to be promising for drug discovery.
authors.affiliation: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Department of Chemistry, East China Normal University , Shanghai, 200062, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Qiu
authors.forename: Lixin
authors.initials: L
authors.lastname: Gao
authors.forename: Jixing
authors.initials: J
authors.lastname: Tang
authors.forename: Dongwei
authors.initials: D
authors.lastname: Wang
authors.forename: Xin
authors.initials: X
authors.lastname: Guo
authors.forename: Shunying
authors.initials: S
authors.lastname: Liu
authors.forename: Liping
authors.initials: L
authors.lastname: Yang
authors.forename: Jia
authors.initials: J
authors.lastname: Li
authors.forename: Wenhao
authors.initials: W
authors.lastname: Hu
mesh_terms: D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004952:Esters; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D056564:Sirtuin 1 / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D004952:Esters; D007097:Imines; C482356:N-sulfonylimine; D013450:Sulfones; C516607:PTPN1 protein, human; D054562:Protein Tyrosine Phosphatase, Non-Receptor Type 1; C447939:SIRT1 protein, human; D056564:Sirtuin 1