Enantiomeric Resolution and Absolute Configuration of a Chiral δ-Lactam, Useful Intermediate for the Synthesis of Bioactive Compounds.
X-ray diffraction
absolute configuration assignment
chiral resolution
enantioselective HPLC
lactam scaffold
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
19 Dec 2020
19 Dec 2020
Historique:
received:
02
12
2020
revised:
15
12
2020
accepted:
18
12
2020
entrez:
23
12
2020
pubmed:
24
12
2020
medline:
10
4
2021
Statut:
epublish
Résumé
During the past several years, the frequency of discovery of new molecular entities based on γ- or δ-lactam scaffolds has increased continuously. Most of them are characterized by the presence of at least one chiral center. Herein, we present the preparation, isolation and the absolute configuration assignment of enantiomeric 2-(4-bromophenyl)-1-isobutyl-6-oxopiperidin-3-carboxylic acid (
Identifiants
pubmed: 33352660
pii: molecules25246023
doi: 10.3390/molecules25246023
pmc: PMC7766352
pii:
doi:
Substances chimiques
Biological Factors
0
Lactams
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Références
Infect Disord Drug Targets. 2018;18(2):88-95
pubmed: 28356054
J Med Chem. 2020 Jan 23;63(2):441-469
pubmed: 31550151
J Org Chem. 1969 Oct;34(10):3187-9
pubmed: 5811404
Acta Crystallogr B Struct Sci Cryst Eng Mater. 2013 Jun;69(Pt 3):249-59
pubmed: 23719469
Int J Mol Sci. 2019 Jun 06;20(11):
pubmed: 31174387
Ann Hematol. 2014 Jan;93(1):1-11
pubmed: 24018623
Sci Rep. 2018 Sep 13;8(1):13780
pubmed: 30214075
Eur J Med Chem. 2017 Apr 21;130:286-307
pubmed: 28254700
Biogerontology. 2014 Dec;15(6):587-610
pubmed: 25231915
J Pharm Biomed Anal. 2017 Sep 10;144:41-51
pubmed: 28118957
Hindustan Antibiot Bull. 1972 May;14(1):184-90
pubmed: 4209881
ACS Comb Sci. 2014 Mar 10;16(3):146-53
pubmed: 24479637
Org Biomol Chem. 2016 Nov 2;14(43):10134-10156
pubmed: 27748489
Org Lett. 2015 Aug 7;17(15):3930-3
pubmed: 26226189
J Med Chem. 2017 Aug 10;60(15):6649-6663
pubmed: 28598634
J Med Chem. 2007 Dec 27;50(26):6725-9
pubmed: 18052024
Curr Top Med Chem. 2011;11(7):760-70
pubmed: 21291399
J Nat Prod. 2019 Nov 22;82(11):3056-3064
pubmed: 31668072
Drugs. 2018 Nov;78(16):1741-1750
pubmed: 30406902
Chirality. 2008 May 15;20(5):681-90
pubmed: 17924422
Chirality. 2016 May;28(5):434-40
pubmed: 27095007
ACS Med Chem Lett. 2020 Jan 28;11(5):883-888
pubmed: 32435400
ACS Med Chem Lett. 2019 Jan 21;10(4):615-620
pubmed: 30996806
Nat Rev Drug Discov. 2012 Mar 01;11(3):191-200
pubmed: 22378269
Molecules. 2020 Feb 19;25(4):
pubmed: 32093112
Pharmacol Res. 2013 Jul;73:44-54
pubmed: 23643828
Angew Chem Int Ed Engl. 2015 Nov 16;54(47):13933-6
pubmed: 26385475
Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016 Apr;72(Pt 2):171-9
pubmed: 27048719
Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8
pubmed: 25567568
Expert Opin Drug Metab Toxicol. 2013 Apr;9(4):423-40
pubmed: 23330992
Bioorg Med Chem Lett. 2020 Jan 15;30(2):126826
pubmed: 31836441
Expert Opin Drug Discov. 2017 Dec;12(12):1253-1269
pubmed: 28971706
Tetrahedron. 2020 Apr 17;76(16):
pubmed: 32382196
J Chromatogr A. 2011 Aug 12;1218(32):5414-22
pubmed: 21397238
J Org Chem. 1971 Nov;36(22):3404-11
pubmed: 5132298
Org Lett. 2016 Aug 19;18(16):4124-7
pubmed: 27508307
J Med Chem. 2018 Jun 14;61(11):4688-4703
pubmed: 29235859
J Cancer Prev. 2017 Dec;22(4):203-210
pubmed: 29302577
Drugs. 2017 Sep;77(13):1473-1480
pubmed: 28791622
J Chem Inf Model. 2016 Feb 22;56(2):300-7
pubmed: 26838127
Chirality. 2013 Nov;25(11):814-22
pubmed: 24038285
J Pharm Biomed Anal. 2018 Jan 5;147:323-340
pubmed: 28942107
J Med Chem. 2019 May 9;62(9):4731-4741
pubmed: 30964292
Eur J Oral Sci. 2018 Jun;126(3):214-221
pubmed: 29517121
J Appl Crystallogr. 2015 Jan 30;48(Pt 1):3-10
pubmed: 26089746
J Med Chem. 2017 Oct 26;60(20):8257-8267
pubmed: 28587461
Bioorg Chem. 2020 Jul;100:103886
pubmed: 32371249
Chem Rev. 2009 Jan;109(1):164-89
pubmed: 19140773
Nat Rev Drug Discov. 2020 Feb;19(2):93-111
pubmed: 31836861
Org Biomol Chem. 2016 Sep 21;14(37):8864-8872
pubmed: 27714224
ACS Comb Sci. 2017 Nov 13;19(11):702-707
pubmed: 29019643