Reductive Functionalization of Amides in Synthesis and for Modification of Bioactive Compounds.
amide reduction
bioactive compounds
bioisosteres
functionalization
late-stage functionalization
natural products
Journal
Frontiers in chemistry
ISSN: 2296-2646
Titre abrégé: Front Chem
Pays: Switzerland
ID NLM: 101627988
Informations de publication
Date de publication:
2021
2021
Historique:
received:
19
01
2021
accepted:
23
02
2021
entrez:
13
5
2021
pubmed:
14
5
2021
medline:
14
5
2021
Statut:
epublish
Résumé
In this review, applications of the amide reductive functionalization methodology for the synthesis and modification of bioactive compounds are covered. A brief summary of the different protocols is presented in the introduction, followed by the synthetic application of these in late-stage functionalization, leading to known pharmaceuticals or to their derivatives, including bioisosteres, with potential higher activity as the main axis of the article. The synthetic approach to natural products based on amide reduction is also discussed; however, this is given in a condensed form focusing on recent or as yet unexplored applications due to a number of recently published excellent reviews covering this topic. The aim of this review is to illustrate the potential of reductive functionalization of amides as an elegant and useful tool in the synthesis of bioactive compounds and inspire further work in this field.
Identifiants
pubmed: 33981672
doi: 10.3389/fchem.2021.655849
pmc: PMC8107389
doi:
Types de publication
Journal Article
Review
Langues
eng
Pagination
655849Informations de copyright
Copyright © 2021 Czerwiński and Furman.
Déclaration de conflit d'intérêts
The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.
Références
Chemistry. 2020 Jan 13;26(3):611-615
pubmed: 31696589
Chem Sci. 2017 Nov 1;8(11):7492-7497
pubmed: 29163902
Org Lett. 2012 Feb 3;14(3):950-3
pubmed: 22260368
Chemistry. 2010 Nov 15;16(43):12792-6
pubmed: 20938943
ChemMedChem. 2007 Dec;2(12):1693-700
pubmed: 17823898
Angew Chem Int Ed Engl. 2016 Mar 24;55(14):4562-6
pubmed: 26934055
J Org Chem. 2013 Sep 6;78(17):8305-11
pubmed: 23909394
Chem Commun (Camb). 2009 Mar 28;(12):1574-6
pubmed: 19277394
Chem Rev. 2006 Jun;106(6):2531-49
pubmed: 16771458
J Am Chem Soc. 2007 Mar 21;129(11):3408-19
pubmed: 17315870
Chem Rev. 2019 Apr 10;119(7):4684-4716
pubmed: 30875202
J Med Chem. 2015 Nov 12;58(21):8315-59
pubmed: 26200936
Org Lett. 2019 Mar 15;21(6):1868-1871
pubmed: 30817163
Angew Chem Int Ed Engl. 2017 Jan 19;56(4):1087-1091
pubmed: 27990730
J Org Chem. 2017 Oct 6;82(19):10188-10200
pubmed: 28901766
J Am Chem Soc. 2016 Apr 27;138(16):5246-9
pubmed: 27071479
Angew Chem Int Ed Engl. 2010 Apr 12;49(17):3037-40
pubmed: 20301159
Chemistry. 2013 Sep 23;19(39):13075-86
pubmed: 23956001
J Med Chem. 2020 Nov 12;63(21):12290-12358
pubmed: 32686940
Eur J Med Chem. 2016 Nov 10;123:14-20
pubmed: 27474919
Org Lett. 2001 Feb 8;3(3):485-7
pubmed: 11434316
Org Lett. 2020 Oct 2;22(19):7502-7507
pubmed: 32960064
Chem Commun (Camb). 2019 Aug 7;55(64):9436-9439
pubmed: 31304490
J Med Chem. 2018 Jul 26;61(14):5822-5880
pubmed: 29400967
Angew Chem Int Ed Engl. 2017 Mar 20;56(13):3655-3659
pubmed: 28233919
J Am Chem Soc. 2008 Jan 9;130(1):18-9
pubmed: 18076177
Chemistry. 2016 May 17;22(21):7108-14
pubmed: 27038135
Chemistry. 2015 Jan 2;21(1):111-4
pubmed: 25399919
Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12347-12351
pubmed: 30084524
Nat Commun. 2018 Jul 19;9(1):2841
pubmed: 30026608
Angew Chem Int Ed Engl. 2019 Apr 1;58(15):4992-4997
pubmed: 30761712
J Am Chem Soc. 2012 Oct 24;134(42):17482-5
pubmed: 23039372
Org Biomol Chem. 2018 May 30;16(21):3864-3875
pubmed: 29701231
J Am Chem Soc. 2012 Jul 18;134(28):11304-7
pubmed: 22770123
Chem Commun (Camb). 2016 Sep 29;52(80):11967-11970
pubmed: 27722243
Angew Chem Int Ed Engl. 2020 Jul 13;59(29):11903-11907
pubmed: 32329555