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Titolo:
SYNTHESIS, RESOLUTION AND RADIOIODINATION OF DO-2'-PROPENYL)AMINO]TETRALIN-S(-)TRANS-5-OH-PIPAT - NEW DOPAMINE D2-LIKE RECEPTOR-LIGAND
Autore:
CHUMPRADIT S; KUNG MP; VESSOTSKIE J; KUNG HF;
Indirizzi:
UNIV PENN,DEPT RADIOL,3700 MKT ST,ROOM 305 PHILADELPHIA PA 19104 UNIV PENN,DEPT PHARMACOL PHILADELPHIA PA 19104
Titolo Testata:
Journal of labelled compounds & radiopharmaceuticals
fascicolo: 11, volume: 36, anno: 1995,
pagine: 1051 - 1062
SICI:
0362-4803(1995)36:11<1051:SRAROD>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Keywords:
DOPAMINE D2; D3 AND D4 RECEPTORS; I-125; RADIOIODINATION; 5-OH-DPAT; 5-OH-PIPAT;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
15
Recensione:
Indirizzi per estratti:
Citazione:
S. Chumpradit et al., "SYNTHESIS, RESOLUTION AND RADIOIODINATION OF DO-2'-PROPENYL)AMINO]TETRALIN-S(-)TRANS-5-OH-PIPAT - NEW DOPAMINE D2-LIKE RECEPTOR-LIGAND", Journal of labelled compounds & radiopharmaceuticals, 36(11), 1995, pp. 1051-1062

Abstract

A new dopamine D2-like receptor ligand, -[N-n-propyl-N-(3'-iodo-2'-propenyl)amino]tetralin ((R,S)trans-5-OH-PIPAT, (3) under bar), based onhigh affinity dopamine receptor agonist 5-hydroxy-2-[N,N-(di-n-propyl)-2-amino]tetralin (5-OH-DPAT, (1) under bar), was prepared. The synthesis was achieved by a reductive amination of 5-methoxy-2-tetralone with n-propylamine, followed by N-alkylation, to afford 5-methoxy-N-propyl-N-2'-propynyl-2-aminotetralin, (7) under bar. Reduction of (7) under bar with tributyltin hydride gave the tri-n-butyl tin derivative, (8) under bar, which was converted to (9) under bar by an iododemetalation reaction. Demethylation of (9) under bar gave the desired compound,(R,S)trans-5-OH-PIPAT, (3) under bar. The resolved (R) and (S)trans-5-OH-PIPAT, (3) under bar, were also quantitatively prepared. In vitro binding studies showed the stereoselectivity of this new compound for binding to dopamine D2-like receptors. S(-)-(3) under bar displayed high binding affinity, with inhibition constants (K-i) of 0.38, 0.09 and0.67 nM for dopamine D2H (expressed in HEK293 cells), D3 (expressed in Sf9 cells) and D4H receptors (expressed in CHO cells), respectively. Using the same binding assays, the less active R(+) isomer displayed K-i values of 7.29, 4.87 and 16.44 nM for D2H, D3 and D4H receptors, respectively. In addition, radiolabeling was successfully performed, either with the racemic tin derivative, (R,S)-<(11)under bar>, or using the optically resolved tin derivatives R(+)- or S(-)-<(11)under bar>, to give the final radiolabeled product, [I-125]R(+) or S(-)-(3) under bar.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/01/20 alle ore 19:30:25