schliessen

Filtern

 

Bibliotheken

Synthesis of Structurally Diverse N-Substituted Quaternary-Carbon-Containing Small Molecules from α,α-Disubstituted Propargyl Amino Esters

N-containing quaternary stereocenters represent important motifs in medicinal chemistry. However, due to their inherently sterically hindered nature, they remain underrepresented in small molecule screening collections. As such, the development of synthetic routes to generate small molecules that in... Full description

Journal Title: Chemistry (Weinheim an der Bergstrasse Germany), 12 September 2018, Vol.24(51), pp.13681-13687
Main Author: Mateu, Natalia
Other Authors: Kidd, Sarah L , Kalash, Leen , Sore, Hannah F , Madin, Andrew , Bender, Andreas , Spring, David R
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1521-3765 ; PMID: 30011115 Version:1 ; DOI: 10.1002/chem.201803143
Link: http://pubmed.gov/30011115
Zum Text:
SendSend as email Add to Book BagAdd to Book Bag
Staff View
recordid: medline30011115
title: Synthesis of Structurally Diverse N-Substituted Quaternary-Carbon-Containing Small Molecules from α,α-Disubstituted Propargyl Amino Esters
format: Article
creator:
  • Mateu, Natalia
  • Kidd, Sarah L
  • Kalash, Leen
  • Sore, Hannah F
  • Madin, Andrew
  • Bender, Andreas
  • Spring, David R
subjects:
  • Diversity-Oriented Synthesis
  • Drug Discovery
  • Medicinal Chemistry
  • Molecular Diversity
  • Quaternary Stereocenters
ispartof: Chemistry (Weinheim an der Bergstrasse, Germany), 12 September 2018, Vol.24(51), pp.13681-13687
description: N-containing quaternary stereocenters represent important motifs in medicinal chemistry. However, due to their inherently sterically hindered nature, they remain underrepresented in small molecule screening collections. As such, the development of synthetic routes to generate small molecules that incorporate this particular feature are highly desirable. Herein, we describe the diversity-oriented synthesis (DOS) of a diverse collection of structurally distinct small molecules featuring this three-dimensional (3D) motif. The subsequent derivatisation and the stereoselective synthesis exemplified the versatility of this strategy for drug discovery and library enrichment. Chemoinformatic analysis revealed the enhanced sp character of the target library and demonstrated that it represents an attractive collection of biologically diverse small molecules with high scaffold diversity.
language: eng
source:
identifier: E-ISSN: 1521-3765 ; PMID: 30011115 Version:1 ; DOI: 10.1002/chem.201803143
fulltext: fulltext
issn:
  • 15213765
  • 1521-3765
url: Link


@attributes
ID177291998
RANK0.07
NO1
SEARCH_ENGINEprimo_central_multiple_fe
SEARCH_ENGINE_TYPEPrimo Central Search Engine
LOCALfalse
PrimoNMBib
record
control
sourcerecordid30011115
sourceidmedline
recordidTN_medline30011115
sourceformatXML
sourcesystemPC
pqid2070799875
galeid553924067
display
typearticle
titleSynthesis of Structurally Diverse N-Substituted Quaternary-Carbon-Containing Small Molecules from α,α-Disubstituted Propargyl Amino Esters
creatorMateu, Natalia ; Kidd, Sarah L ; Kalash, Leen ; Sore, Hannah F ; Madin, Andrew ; Bender, Andreas ; Spring, David R
ispartofChemistry (Weinheim an der Bergstrasse, Germany), 12 September 2018, Vol.24(51), pp.13681-13687
identifier
subjectDiversity-Oriented Synthesis ; Drug Discovery ; Medicinal Chemistry ; Molecular Diversity ; Quaternary Stereocenters
descriptionN-containing quaternary stereocenters represent important motifs in medicinal chemistry. However, due to their inherently sterically hindered nature, they remain underrepresented in small molecule screening collections. As such, the development of synthetic routes to generate small molecules that incorporate this particular feature are highly desirable. Herein, we describe the diversity-oriented synthesis (DOS) of a diverse collection of structurally distinct small molecules featuring this three-dimensional (3D) motif. The subsequent derivatisation and the stereoselective synthesis exemplified the versatility of this strategy for drug discovery and library enrichment. Chemoinformatic analysis revealed the enhanced sp character of the target library and demonstrated that it represents an attractive collection of biologically diverse small molecules with high scaffold diversity.
languageeng
source
version7
lds50peer_reviewed
links
openurl$$Topenurl_article
backlink$$Uhttp://pubmed.gov/30011115$$EView_this_record_in_MEDLINE/PubMed
openurlfulltext$$Topenurlfull_article
addlink$$Uhttp://exlibris-pub.s3.amazonaws.com/aboutMedline.html$$EView_the_MEDLINE/PubMed_Copyright_Statement
search
creatorcontrib
0Mateu, Natalia
1Kidd, Sarah L
2Kalash, Leen
3Sore, Hannah F
4Madin, Andrew
5Bender, Andreas
6Spring, David R
titleSynthesis of Structurally Diverse N-Substituted Quaternary-Carbon-Containing Small Molecules from α,α-Disubstituted Propargyl Amino Esters
descriptionN-containing quaternary stereocenters represent important motifs in medicinal chemistry. However, due to their inherently sterically hindered nature, they remain underrepresented in small molecule screening collections. As such, the development of synthetic routes to generate small molecules that incorporate this particular feature are highly desirable. Herein, we describe the diversity-oriented synthesis (DOS) of a diverse collection of structurally distinct small molecules featuring this three-dimensional (3D) motif. The subsequent derivatisation and the stereoselective synthesis exemplified the versatility of this strategy for drug discovery and library enrichment. Chemoinformatic analysis revealed the enhanced sp character of the target library and demonstrated that it represents an attractive collection of biologically diverse small molecules with high scaffold diversity.
subject
0Diversity-Oriented Synthesis
1Drug Discovery
2Medicinal Chemistry
3Molecular Diversity
4Quaternary Stereocenters
general
030011115
1English
2MEDLINE/PubMed (U.S. National Library of Medicine)
310.1002/chem.201803143
4MEDLINE/PubMed (NLM)
sourceidmedline
recordidmedline30011115
issn
015213765
11521-3765
rsrctypearticle
creationdate2018
addtitleChemistry (Weinheim an der Bergstrasse, Germany)
searchscope
0medline
1nlm_medline
2MEDLINE
scope
0medline
1nlm_medline
2MEDLINE
lsr4120180912
citationpf 13681 vol 24 issue 51
startdate20180912
enddate20180912
lsr30VSR-Enriched:[galeid, orcidid, pqid]
sort
titleSynthesis of Structurally Diverse N-Substituted Quaternary-Carbon-Containing Small Molecules from α,α-Disubstituted Propargyl Amino Esters
authorMateu, Natalia ; Kidd, Sarah L ; Kalash, Leen ; Sore, Hannah F ; Madin, Andrew ; Bender, Andreas ; Spring, David R
creationdate20180912
lso0120180912
facets
frbrgroupid8527201290126501598
frbrtype5
newrecords20190701
languageeng
creationdate2018
topic
0Diversity-Oriented Synthesis
1Drug Discovery
2Medicinal Chemistry
3Molecular Diversity
4Quaternary Stereocenters
collectionMEDLINE/PubMed (NLM)
prefilterarticles
rsrctypearticles
creatorcontrib
0Mateu, Natalia
1Kidd, Sarah L
2Kalash, Leen
3Sore, Hannah F
4Madin, Andrew
5Bender, Andreas
6Spring, David R
jtitleChemistry (Weinheim An Der Bergstrasse, Germany)
toplevelpeer_reviewed
delivery
delcategoryRemote Search Resource
fulltextfulltext
addata
aulast
0Mateu
1Kidd
2Kalash
3Sore
4Madin
5Bender
6Spring
aufirst
0Natalia
1Sarah L
2Leen
3Hannah F
4Andrew
5Andreas
6David R
au
0Mateu, Natalia
1Kidd, Sarah L
2Kalash, Leen
3Sore, Hannah F
4Madin, Andrew
5Bender, Andreas
6Spring, David R
atitleSynthesis of Structurally Diverse N-Substituted Quaternary-Carbon-Containing Small Molecules from α,α-Disubstituted Propargyl Amino Esters
jtitleChemistry (Weinheim an der Bergstrasse, Germany)
risdate20180912
volume24
issue51
spage13681
pages13681-13687
issn0947-6539
eissn1521-3765
formatjournal
genrearticle
ristypeJOUR
abstractN-containing quaternary stereocenters represent important motifs in medicinal chemistry. However, due to their inherently sterically hindered nature, they remain underrepresented in small molecule screening collections. As such, the development of synthetic routes to generate small molecules that incorporate this particular feature are highly desirable. Herein, we describe the diversity-oriented synthesis (DOS) of a diverse collection of structurally distinct small molecules featuring this three-dimensional (3D) motif. The subsequent derivatisation and the stereoselective synthesis exemplified the versatility of this strategy for drug discovery and library enrichment. Chemoinformatic analysis revealed the enhanced sp character of the target library and demonstrated that it represents an attractive collection of biologically diverse small molecules with high scaffold diversity.
doi10.1002/chem.201803143
pmid30011115
orcididhttp://orcid.org/0000-0001-9451-0666
date2018-09-12