Synthesis of DNA-coupled isoquinolones and pyrrolidines by solid phase ytterbium- and silver-mediated imine chemistry.
Journal
MedChemComm
ISSN: 2040-2511
Titre abrégé: Medchemcomm
Pays: England
ID NLM: 101531525
Informations de publication
Date de publication:
01 Jul 2019
01 Jul 2019
Historique:
received:
25
01
2019
accepted:
21
02
2019
entrez:
9
8
2019
pubmed:
9
8
2019
medline:
9
8
2019
Statut:
epublish
Résumé
DNA-encoded libraries of chemically synthesized compounds are an important small molecule screening technology. The synthesis of encoded compounds in solution is currently restricted to a few DNA-compatible and water-tolerant reactions. Encoded compound synthesis of short DNA-barcodes covalently connected to solid supports benefits from a broad range of choices of organic solvents. Here, we show that this encoded chemistry approach allows for the synthesis of DNA-coupled isoquinolones by an Yb(iii)-mediated Castagnoli-Cushman reaction under anhydrous reaction conditions and for the synthesis of highly substituted pyrrolidines by Ag(i)-mediated 1,3-dipolar azomethine ylide cycloaddition. An encoding scheme for these DNA-barcoded compounds based on a DNA hairpin is demonstrated.
Identifiants
pubmed: 31391880
doi: 10.1039/c9md00042a
pii: c9md00042a
pmc: PMC6644566
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1082-1093Références
Chemistry. 2014 Dec 8;20(50):16613-9
pubmed: 25322724
Chem Rev. 2015 Jun 10;115(11):5366-412
pubmed: 25961125
J Med Chem. 2016 Jul 28;59(14):6629-44
pubmed: 26914744
Bioconjug Chem. 2015 Aug 19;26(8):1623-32
pubmed: 26024553
Medchemcomm. 2017 Jul 12;8(8):1614-1617
pubmed: 30108872
Bioconjug Chem. 2014 Aug 20;25(8):1453-61
pubmed: 25061844
J Org Chem. 1977 Apr 1;42(7):1111-6
pubmed: 845705
Proc Natl Acad Sci U S A. 2008 Nov 18;105(46):17670-5
pubmed: 19001273
Org Lett. 2015 Aug 7;17(15):3930-3
pubmed: 26226189
Bioconjug Chem. 2017 Apr 19;28(4):1076-1083
pubmed: 28233987
Proc Natl Acad Sci U S A. 2014 Dec 16;111(50):E5455-62
pubmed: 25453091
ACS Chem Biol. 2016 Feb 19;11(2):296-307
pubmed: 26820267
Org Biomol Chem. 2018 Apr 18;16(15):2591-2601
pubmed: 29560980
ACS Comb Sci. 2019 Feb 11;21(2):69-74
pubmed: 30615417
Chem Soc Rev. 2011 Dec;40(12):5707-17
pubmed: 21674077
Chimia (Aarau). 2013;67(5):340-8
pubmed: 23863269
ACS Comb Sci. 2018 May 14;20(5):251-255
pubmed: 29648439
Nat Commun. 2010 Sep 21;1:80
pubmed: 20865796
J Org Chem. 2005 Jan 7;70(1):350-2
pubmed: 15624947
PLoS Biol. 2004 Jul;2(7):E173
pubmed: 15221027
J Am Chem Soc. 2008 Nov 19;130(46):15611-26
pubmed: 18956864
J Am Chem Soc. 2014 Aug 27;136(34):11853-9
pubmed: 25074019
Org Biomol Chem. 2018 Nov 14;16(44):8446-8461
pubmed: 30378620
Proc Natl Acad Sci U S A. 1992 Jun 15;89(12):5381-3
pubmed: 1608946
J Org Chem. 2018 Oct 19;83(20):12722-12733
pubmed: 30226770
J Med Chem. 2014 Dec 26;57(24):10257-74
pubmed: 25255204
Angew Chem Int Ed Engl. 2015 Mar 23;54(13):3927-31
pubmed: 25650139
Bioorg Med Chem Lett. 2009 May 1;19(9):2400-3
pubmed: 19346127
J Med Chem. 2017 Feb 23;60(4):1247-1261
pubmed: 28151659
ChemMedChem. 2008 Jul;3(7):1118-28
pubmed: 18428185
Curr Opin Chem Biol. 2010 Jun;14(3):347-61
pubmed: 20303320
Nat Chem. 2018 Jul;10(7):704-714
pubmed: 29610462
ACS Comb Sci. 2016 Apr 11;18(4):182-7
pubmed: 26971959
Nature. 2017 May 4;545(7652):112-115
pubmed: 28445455
Medchemcomm. 2018 May 17;9(7):1188-1193
pubmed: 30109007
J Am Chem Soc. 2009 Jan 28;131(3):1322-7
pubmed: 19123795
ACS Chem Biol. 2017 Nov 17;12(11):2730-2736
pubmed: 29043777
Nat Rev Drug Discov. 2017 Feb;16(2):131-147
pubmed: 27932801
ACS Comb Sci. 2015 Jan 12;17(1):1-4
pubmed: 25459065
RSC Adv. 2018 Dec 10;8(72):41226-41236
pubmed: 35559303
J Med Chem. 2016 Sep 8;59(17):7950-62
pubmed: 27505686
Curr Opin Chem Biol. 2010 Jun;14(3):396-403
pubmed: 20346729
Nat Biotechnol. 2004 May;22(5):568-74
pubmed: 15097996
European J Org Chem. 2018 Nov 25;2018(43):5889-5904
pubmed: 30555273
Proc Natl Acad Sci U S A. 1997 Apr 1;94(7):2805-10
pubmed: 9096301
J Med Chem. 2007 Mar 8;50(5):897-900
pubmed: 17269759
Org Biomol Chem. 2017 Oct 18;15(40):8648-8654
pubmed: 28981134
J Am Chem Soc. 2013 May 15;135(19):7223-34
pubmed: 23641733
Chem Sci. 2017 May 1;8(5):3356-3361
pubmed: 28507705
Science. 2004 Sep 10;305(5690):1601-5
pubmed: 15319493
J Am Chem Soc. 2013 Nov 27;135(47):17727-30
pubmed: 24229415
Proc Natl Acad Sci U S A. 2017 Feb 14;114(7):1708-1713
pubmed: 28130548
Chem Rev. 2009 Jan;109(1):164-89
pubmed: 19140773
J Org Chem. 1999 Jun 25;64(13):4749-4761
pubmed: 11674548
Molecules. 2016 Dec 02;21(12):
pubmed: 27918451
Nat Chem Biol. 2009 Sep;5(9):647-54
pubmed: 19648931
ACS Comb Sci. 2017 Nov 13;19(11):702-707
pubmed: 29019643