ChemInform Abstract: α‐Hydroxy Phosphinyl‐Based Inhibitors of Human Renin.

Abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Structure-Guided Design and Optimization of Dipeptidyl Inhibitors of Norovirus 3CL Protease. Structure–Activity Relationships and Biochemical, X-ray Crystallographic, Cell-Based, and In Vivo Studies

“…The enantiomeric purity of the aldehyde was consistently high, with the amount of epimerized aldehyde ranging between 0 and 10%, depending on the structure of the dipeptidyl aldehyde. Further reaction of the aldehyde with diethyl phosphite in the presence of diisopropyl ethyl amine yielded the corresponding α-hydroxyphosphonate as a mixture of epimers . The corresponding bisulfite adducts were readily obtained as white solids by stirring the aldehydes with sodium bisulfite in an ethyl acetate/water mixture .…”

“…Further reaction of the aldehyde with diethyl phosphite in the presence of diisopropyl ethyl amine yielded the corresponding α-hydroxyphosphonate as a mixture of epimers. 23 The corresponding bisulfite adducts were readily obtained as white solids by stirring the aldehydes with sodium bisulfite in an ethyl acetate/water mixture. 24 Reaction of the aldehyde with cyclopropyl isonitrile followed by Dess−Martin oxidation of the α-hydroxy cyclopropyl amide yielded the desired α-ketoamides.…”

Asymmetric Construction of Tertiary/Secondary Carbon–Phosphorus Bonds via Bifunctional Phosphonium Salt Catalyzed 1,6-Addition

“…The successful implementation of this strategy would provide an expedient access to previously challenging chiral scaffolds bearing tertiary/secondary C−P bonds with quatarnary diarylacetonitrile units, both of which represent important building blocks in organic synthesis together with broad biomedical applications. 38,39 However, significant challenges are anticipated in exploring this asymmetric remote C−P bond formation (Figure 1d, the latter). One of the big issues is that the δ,δ′-disubstituted p-QMs have less reactivity presumably due to the steric hindrance around the reactive sites and particularly have rarely been employed in asymmetric organic reactions.…”

Recent Advances in H-Phosphonate Chemistry. Part 2. Synthesis of C-Phosphonate Derivatives

“…Since the biological activity of phosphonic acid derivatives is primarily determined by the absolute configuration of the α-carbon [68,69], enantio/diastereoselective synthesis of α-hydroxyphosphonates has became a focus of synthetic endeavors in recent years [53,54].…”