About: Aryl methylene ketones and fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome (SARS) 3C-like proteinase

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About: Aryl methylene ketones and fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome (SARS) 3C-like proteinase Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : wasabi.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
title	Aryl methylene ketones and fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome (SARS) 3C-like proteinase
Creator	Yin, Jiang Niu, Chunying Zhang, Jianmin Huitema, Carly Eltis, Lindsay James, Michael Vederas, John
source	Elsevier; Medline; PMC
abstract	Abstract The severe acute respiratory syndrome (SARS) virus depends on a chymotrypsin-like cysteine proteinase (3CLpro) to process the translated polyproteins to functional viral proteins. This enzyme is a target for the design of potential anti-SARS drugs. A series of ketones and corresponding mono- and di-fluoro ketones having two or three aromatic rings were synthesized as possible reversible inhibitors of SARS 3CLpro. The design was based on previously established potent inhibition of the enzyme by oxa analogues (esters), which also act as substrates. Structure–activity relationships and modeling studies indicate that three aromatic rings, including a 5-bromopyridin-3-yl moiety, are key features for good inhibition of SARS 3CLpro. Compound 11d, 2-(5-bromopyridin-3-yl)-1-(5-(4-chlorophenyl)furan-2-yl)ethanone and its α-monofluorinated analogue 12d, gave the best reversible inhibition with IC50 values of 13μM and 28μM, respectively. In contrast to inhibitors having two aromatic rings, α-fluorination of compounds with three rings unexpectedly decreased the inhibitory activity.
has issue date	2008-10-31(xsd:dateTime)
bibo:doi	10.1016/j.bioorg.2008.01.001
bibo:pmid	18295820
has license	els-covid
sha1sum (hex)	83992aaca8041550749a8bb1a6607116135ada38
schema:url	https://doi.org/10.1016/j.bioorg.2008.01.001
resource representing a document's title	Aryl methylene ketones and fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome (SARS) 3C-like proteinase
has PubMed Central identifier	PMC7112044
has PubMed identifier	18295820
schema:publication	Bioorganic Chemistry
resource representing a document's body	covid:83992aaca8041550749a8bb1a6607116135ada38#body_text
is schema:about of	named entity 'furan' named entity 'inhibition' named entity 'esters' named entity 'Aryl' named entity 'reversible' covid:arg/83992aaca8041550749a8bb1a6607116135ada38 named entity 'series' named entity 'compounds' named entity 'values' named entity 'inhibitors' named entity 'substrates' named entity 'translated' named entity 'aromatic rings' named entity 'inhibitory activity' named entity 'esters' named entity 'enzyme' named entity 'chymotrypsin-like' named entity 'cysteine' named entity 'SARS' named entity 'substrates' named entity 'SARS' named entity 'SARS' named entity 'aromatic rings' named entity 'proteinase' named entity 'ketones' named entity 'proteinase' named entity 'aqueous' named entity 'EtOAc' named entity 'hexanes' named entity 'Nucleophilic attack' named entity 'solvent' named entity 'reflux' named entity 'THF' named entity 'Esterification' named entity 'causative agent' named entity 'hemithioacetal' named entity 'active site' named entity 'celite' named entity '7.9' named entity 'EtOAc' named entity 'mmol' named entity 'peptide' named entity 'aqueous' named entity 'COCH' named entity 'THF' named entity 'esters' named entity 'ketone' named entity 'halogen' named entity 'NaHCO' named entity 'noncovalent' named entity 'molecular docking' named entity 'mmol' named entity 'EtOAc' named entity 'potassium hydroxide' named entity 'MgSO' named entity 'EtOAc' named entity 'mmol' named entity 'carbonyl' named entity 'silica gel' named entity 'TLC' named entity 'EtOAc' named entity 'solvent' named entity 'solvent' named entity 'esterases' named entity 'salt' named entity 'sublimes' named entity 'column chromatography' named entity 'mmol' named entity 'acetic acid' named entity 'conformations' named entity 'esters' named entity 'silica gel' named entity 'CuCl' named entity 'HCl' named entity 'esters'

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