Synthesis and dopamine receptor binding of dihydrexidine and SKF 38393 catecholamine-based analogues.


Journal

Amino acids
ISSN: 1438-2199
Titre abrégé: Amino Acids
Pays: Austria
ID NLM: 9200312

Informations de publication

Date de publication:
Jan 2022
Historique:
received: 11 10 2021
accepted: 17 11 2021
pubmed: 30 11 2021
medline: 5 4 2022
entrez: 29 11 2021
Statut: ppublish

Résumé

Dopamine is an important neurotransmitter that regulates numerous essential functions, including cognition and voluntary movement. As such, it serves as an important scaffold for synthesis of novel analogues as part of drug development effort to obtain drugs for treatment of neurodegenerative diseases, such as Parkinson's disease. To that end, similarity search of the ZINC database based on two known dopamine-1 receptor (D1R) agonists, dihydrexidine (DHX) and SKF 38393, respectively, was used to predict novel chemical entities with potential binding to D1R. Three compounds that showed the highest similarity index were selected for synthesis and bioactivity profiling. All main synthesis products as well as the isolated intermediates, were properly characterized. The physico-chemical analyses were performed using HRESIMS, GC/MS, LC/MS with UV-Vis detection, and FTIR,

Identifiants

pubmed: 34842969
doi: 10.1007/s00726-021-03106-4
pii: 10.1007/s00726-021-03106-4
doi:

Substances chimiques

Catecholamines 0
Phenanthridines 0
Receptors, Dopamine D1 0
dihydrexidine 32D64VH037
2,3,4,5-Tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine 67287-49-4

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

85-98

Subventions

Organisme : FAPESP
ID : 2016/10149-0

Informations de copyright

© 2021. The Author(s), under exclusive licence to Springer-Verlag GmbH Austria, part of Springer Nature.

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Auteurs

Suzane Rosa da Silva (SR)

Laboratory of Fine Organic Chemistry, Department of Chemistry and Biochemistry, Faculty of Sciences and Technology of São Paulo State University, Presidente Prudente, São Paulo, 19060-900, Brazil.

Predrag Kalaba (P)

Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090, Vienna, Austria.

Anna Fabišiková (A)

Mass Spectrometry Centre, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.

Martin Zehl (M)

Mass Spectrometry Centre, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.
Department of Analytical Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.

Vladimir Dragačević (V)

Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090, Vienna, Austria.

Luana Ribeiro Dos Anjos (LR)

Laboratory of Fine Organic Chemistry, Department of Chemistry and Biochemistry, Faculty of Sciences and Technology of São Paulo State University, Presidente Prudente, São Paulo, 19060-900, Brazil.

Philip John Neill (PJ)

Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090, Vienna, Austria.

Marcus Wieder (M)

Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090, Vienna, Austria.

Alexander Prado-Roller (A)

Centre for X-Ray Structure Analysis at Faculty of Chemistry, University of Vienna, Währinger Straße 40-42, 1090, Vienna, Austria.

Natalie Gajic (N)

Centre for X-Ray Structure Analysis at Faculty of Chemistry, University of Vienna, Währinger Straße 40-42, 1090, Vienna, Austria.

Vinicius Palaretti (V)

Department of Chemistry, Faculty of Philosophy, Sciences and Letters of Ribeirão Preto, University of São Paulo, Avenida dos Bandeirantes, 3900, Ribeirão Preto, SP, 14040-901, Brazil.

Gil Valdo Jose da Silva (GVJ)

Department of Chemistry, Faculty of Philosophy, Sciences and Letters of Ribeirão Preto, University of São Paulo, Avenida dos Bandeirantes, 3900, Ribeirão Preto, SP, 14040-901, Brazil.

Christian Pifl (C)

Department of Molecular Neurosciences, Centre for Brain Research, Medical University of Vienna, Spitalgasse 4, 1090, Vienna, Austria.

Gert Lubec (G)

Department of Neuroproteomics, Paracelsus Medical University, 5020, Salzburg, Austria. gert.lubec@lubeclab.com.

Eduardo R Perez Gonzalez (ERP)

Laboratory of Fine Organic Chemistry, Department of Chemistry and Biochemistry, Faculty of Sciences and Technology of São Paulo State University, Presidente Prudente, São Paulo, 19060-900, Brazil. eduardo.gonzalez@unesp.br.

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