Gram-Scale Synthesis of 1,8-Naphthyridines in Water: The Friedlander Reaction Revisited.
Journal
ACS omega
ISSN: 2470-1343
Titre abrégé: ACS Omega
Pays: United States
ID NLM: 101691658
Informations de publication
Date de publication:
27 Jul 2021
27 Jul 2021
Historique:
received:
28
05
2021
accepted:
29
06
2021
entrez:
2
8
2021
pubmed:
3
8
2021
medline:
3
8
2021
Statut:
epublish
Résumé
The products of the Friedlander reaction, i.e., 1,8-naphthyridines, have far-reaching impacts in materials science, chemical biology, and medicine. The reported synthetic methodologies elegantly orchestrate the diverse synthetic routes of naphthyridines but require harsh reaction conditions, organic solvents, and expensive metal catalysts. Here, we introduce gram-scale synthesis of 1,8-naphthyridines in water using an inexpensive and biocompatible ionic liquid (IL) as a catalyst. This is the first-ever report on the synthesis of naphthyridines in water. This is a one-step reaction, and the product separation is relatively easy. The choline hydroxide (ChOH) is used as a metal-free, nontoxic, and water-soluble catalyst. In comparison to other catalysts reported in the literature, ChOH has the advantage of forming an additional hydrogen bond with the reactants, which is the vital step for the reaction to happen in water. Density functional theory (DFT) and noncovalent interaction (NCI) plot index analysis provide the plausible reaction mechanism for the catalytic cycle and confirm that hydrogen bonds with the IL catalyst are pivotal to facilitate the reaction. Molecular docking and molecular dynamics (MD) simulations are also performed to demonstrate the potentialities of the newly synthesized products as drugs. Through MD simulations, it was established that the tetrahydropyrido derivative of naphthyridine (
Identifiants
pubmed: 34337267
doi: 10.1021/acsomega.1c02798
pmc: PMC8320145
doi:
Types de publication
Journal Article
Langues
eng
Pagination
19304-19313Informations de copyright
© 2021 The Authors. Published by American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
Références
J Phys Chem B. 2019 Nov 27;123(47):10100-10109
pubmed: 31682757
Chem Asian J. 2020 Jan 17;15(2):279-286
pubmed: 31793204
Molecules. 2012 Oct 24;17(11):12506-20
pubmed: 23095894
Nat Rev Drug Discov. 2003 Mar;2(3):192-204
pubmed: 12612645
Blood Rev. 2015 Jan;29(1):1-9
pubmed: 25441922
Chem Commun (Camb). 2020 Apr 21;56(31):4284-4287
pubmed: 32182324
ACS Chem Biol. 2018 Aug 17;13(8):2190-2202
pubmed: 29800515
J Med Chem. 2019 Apr 11;62(7):3741-3752
pubmed: 30860382
Oncol Lett. 2018 Aug;16(2):1431-1438
pubmed: 30008821
Bioorg Med Chem Lett. 2000 Jun 5;10(11):1155-8
pubmed: 10866370
Angew Chem Int Ed Engl. 2006 Feb 27;45(10):1520-43
pubmed: 16491487
Nat Struct Mol Biol. 2018 Feb;25(2):170-175
pubmed: 29379174
Org Lett. 2000 Dec 28;2(26):4189-91
pubmed: 11150196
Chemistry. 2003 Jan 20;9(2):407-14
pubmed: 12532289
J Am Chem Soc. 2018 May 30;140(21):6668-6684
pubmed: 29763323
Nucleosides Nucleotides Nucleic Acids. 2000 Sep;19(9):1381-96
pubmed: 11092310
Drug Discov Today. 2002 Jun 1;7(11):S83-8
pubmed: 12047885
J Chem Theory Comput. 2011 Mar 8;7(3):625-632
pubmed: 21516178
ACS Chem Biol. 2017 Oct 20;12(10):2563-2569
pubmed: 28825963
J Org Chem. 2014 Oct 17;79(20):9830-4
pubmed: 25222052
Adv Drug Deliv Rev. 2001 Mar 1;46(1-3):3-26
pubmed: 11259830
Angew Chem Int Ed Engl. 2016 Mar 1;55(10):3438-41
pubmed: 26833677
Chemistry. 2018 May 7;24(26):6672-6695
pubmed: 29465785
J Med Chem. 2015 Jun 25;58(12):4874-82
pubmed: 25738967
Angew Chem Int Ed Engl. 2018 Dec 10;57(50):16496-16500
pubmed: 30347500
Molecules. 2015 May 12;20(5):8499-520
pubmed: 25985354
J Med Chem. 2010 Jul 22;53(14):5129-43
pubmed: 20575555
J Phys Chem A. 2019 Mar 21;123(11):2227-2236
pubmed: 30802055
J Med Chem. 2008 Apr 10;51(7):2062-77
pubmed: 18324764
Acta Crystallogr C Struct Chem. 2018 Nov 1;74(Pt 11):1547-1552
pubmed: 30398212
J Am Chem Soc. 2010 May 12;132(18):6498-506
pubmed: 20394428
Acc Chem Res. 2020 Aug 18;53(8):1580-1592
pubmed: 32677432
Chem Sci. 2019 Jun 21;10(31):7426-7432
pubmed: 31489165
Eur J Med Chem. 2019 Mar 15;166:381-389
pubmed: 30739821
J Mol Med (Berl). 2014 Jan;92(1):53-64
pubmed: 24005829
ChemistryOpen. 2016 Aug 17;5(5):460-469
pubmed: 27777839
Chem Rev. 2009 Jun;109(6):2652-71
pubmed: 19361199
J Org Chem. 2018 Apr 6;83(7):3624-3632
pubmed: 29570285
Angew Chem Int Ed Engl. 2005 May 20;44(21):3275-9
pubmed: 15844112
J Med Chem. 2014 Jun 26;57(12):5190-202
pubmed: 24901667
ACS Chem Neurosci. 2017 Dec 20;8(12):2708-2721
pubmed: 28872831
ACS Cent Sci. 2018 Dec 26;4(12):1642-1651
pubmed: 30648148
Org Lett. 2002 Jan 24;4(2):217-20
pubmed: 11796054
Chem Commun (Camb). 2004 May 7;(9):1096-7
pubmed: 15116202
Chem Commun (Camb). 2001 Dec 7;(23):2399-407
pubmed: 12239988
Medchemcomm. 2019 Jun 28;10(10):1719-1739
pubmed: 31803393
Molecules. 2019 Dec 05;24(24):
pubmed: 31817456
ChemMedChem. 2014 Jun;9(6):1161-8
pubmed: 24799414