About: Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor

Facets (new session)
Description
Metadata
Settings
- owl:sameAs
- Inference Rule:

About: Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor Goto Sponge NotDistinct Permalink

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

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
has title	Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor
Creator	Akaji, Kenichi Hattori, Yasunao Kobayashi, Kazuya Yoshizawa, Shin-Ichiro
Source	Elsevier; Medline; PMC
abstract	Abstract An octahydroisochromene scaffold has been introduced into a known SARS 3CL protease inhibitor as a novel hydrophobic core to interact with the S2 pocket of the protease. An alkyl or aryl substituent was also introduced at the 1-position of the octahydroisochromene scaffold and expected to introduce additional interactions with the protease. Sharpless–Katsuki asymmetric epoxidation and Sharpless asymmetric dihydroxylation were employed to construct the octahydroisochromene scaffold. The introductions of the P1 site His-al and the substituent at 1-position was achieved using successive reductive amination reactions. Our initial evaluations of the diastereo-isomeric mixtures (16a–d) revealed that the octahydroisochromene moiety functions as a core hydrophobic scaffold for the S2 pocket of the protease and the substituent at the 1-position may form additional interactions with the protease. The inhibitory activities of the diastereoisomerically-pure inhibitors (3a–d) strongly suggest that a specific stereo-isomer of the octahydroisochromene scaffold, (1S, 3S) 3b, directs the P1 site imidazole, the warhead aldehyde, and substituent at the 1-position of the fused ring to their appropriate pockets in the protease.
has issue date	2020-02-15(xsd:dateTime)
bibo:doi	10.1016/j.bmc.2019.115273
bibo:pmid	31926775
has license	els-covid
sha1sum (hex)	dfdbbed7b06c9e9c988682c4371629b522c33a15
schema:url	https://doi.org/10.1016/j.bmc.2019.115273
resource representing a document's title	Evaluation of an octahydroisochromene scaffold used as a novel SARS 3CL protease inhibitor
has PubMed Central identifier	PMC7127348
has PubMed identifier	31926775
schema:publication	Bioorganic & Medicinal Chemistry
resource representing a document's body	covid:dfdbbed7b06c9e9c988682c4371629b522c33a15#body_text
is schema:about of	named entity 'USED' named entity 'successive' named entity 'imidazole' named entity 'hydrophobic' named entity 'mixtures' named entity 'site' named entity 'protease' named entity 'Sharpless asymmetric dihydroxylation' named entity 'moiety' named entity 'USING' named entity 'ADDITIONAL' named entity 'INTRODUCE' named entity 'SARS' named entity 'FUSED' named entity 'FORM' named entity 'EXPECTED' named entity 'SUBSTITUENT' named entity 'HIS-' named entity 'SITE' named entity 'ACTIVITIES' named entity 'KNOWN' named entity 'THEIR' named entity 'RING' named entity 'REVEALED' named entity 'INTRODUCED' named entity 'HYDROPHOBIC' named entity 'REDUCTIVE AMINATION' named entity 'ALKYL' named entity 'EMPLOYED' named entity 'PROTEASE' named entity 'PURE' named entity 'SPECIFIC' named entity 'EVALUATIONS' named entity 'OUR' named entity 'MOIETY' named entity 'ALDEHYDE' named entity 'CONSTRUCT' named entity 'INHIBITORS' named entity 'SCAFFOLD' named entity 'INHIBITORY' named entity 'SUCCESSIVE' named entity 'NOVEL' named entity 'INTERACTIONS' named entity 'INITIAL' named entity 'CORE' named entity 'SUGGEST' named entity 'REACTIONS' named entity 'EVALUATION' named entity 'PROTEASE INHIBITOR' named entity 'PROTEASE INHIBITOR' named entity 'NOVEL' named entity 'SARS' named entity 'SCAFFOLD' named entity 'MIXTURES' named entity 'FUNCTIONS' named entity 'INTRODUCED INTO' named entity 'ISOMER' named entity 'TO INTERACT WITH' named entity 'STEREO' named entity 'SHARPLESS-KATSUKI ASYMMETRIC EPOXIDATION' named entity 'APPROPRIATE' named entity 'IMIDAZOLE' named entity 'SHARPLESS ASYMMETRIC DIHYDROXYLATION' named entity 'POSITION' covid:arg/dfdbbed7b06c9e9c988682c4371629b522c33a15 named entity 'directs' named entity 'pockets' named entity 'substituent' named entity 'protease' named entity 'substituent' named entity 'aldehyde' named entity 'protease' named entity 'imidazole' named entity 'fused ring' named entity 'isomer' named entity 'protease' named entity '1.96' named entity 'Butyl'

Faceted Search & Find service v1.13.91 as of Mar 24 2020

Alternative Linked Data Documents: Sponger | ODE Content Formats:

RDF

ODATA

Microdata

About

OpenLink Virtuoso version 07.20.3229 as of Jul 10 2020, on Linux (x86_64-pc-linux-gnu), Single-Server Edition (94 GB total memory)
Data on this page belongs to its respective rights holders.
Virtuoso Faceted Browser Copyright © 2009-2024 OpenLink Software