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Titolo:
A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one (J-113397), the first non-peptide ORL-1 receptor antagonist
Autore:
De Risi, C; Pollini, GP; Trapella, C; Peretto, I; Ronzoni, S; Giardina, GAM;
Indirizzi:
Univ Ferrara, Dipartimento Sci Farmaceut, I-44100 Ferrara, Italy Univ Ferrara Ferrara Italy I-44100 Sci Farmaceut, I-44100 Ferrara, Italy SmithKline Beecham SpA, Dept Med Chem, I-20021 Milan, Italy SmithKline Beecham SpA Milan Italy I-20021 ed Chem, I-20021 Milan, Italy
Titolo Testata:
BIOORGANIC & MEDICINAL CHEMISTRY
fascicolo: 7, volume: 9, anno: 2001,
pagine: 1871 - 1877
SICI:
0968-0896(200107)9:7<1871:ANSAT1>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
OPIOID RECEPTOR; NOCICEPTIN/ORPHANIN FQ; IN-VITRO; AGONISTS; CLONING; MEMBER; FAMILY; POTENT;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
16
Recensione:
Indirizzi per estratti:
Indirizzo: Pollini, GP Univ Ferrara, Dipartimento Sci Farmaceut, Via Fossato Mortara 19, I-44100 Ferrara, Italy Univ Ferrara Via Fossato Mortara 19 Ferrara Italy I-44100 aly
Citazione:
C. De Risi et al., "A new synthetic approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one (J-113397), the first non-peptide ORL-1 receptor antagonist", BIO MED CH, 9(7), 2001, pp. 1871-1877

Abstract

An efficient approach to 1-[(3R,4R)-1-cyclooctylmethyl-3-hydroxymethyl-4-piperidyl]-3-ethyl-1,3-dihydro-benzimidazol-2-one (J-113397) 1, the first non-peptide ORL-1 receptor antagonist described in literature, is outlined. After construction of the piperidine framework through Dieckmann cyclizationof the Michael adduct 8 of cyclooctylmethylamine to methyl acrylate, condensation with o-phenylendiamine produced the beta -enamino ester 2. which has been conveniently used to construct the benzimidazolone substituent at C-4. Catalytic hydrogenation of intermediate II followed by base-promoted cis-trans isomerization of the key compound 12 led to the formation of ester 13, which was converted to the racemic title compound by LiAlH4 reduction. The pure enantiomers were obtained by chiral preparative HPLC separation using a derivatized cellulose-based stationary phase, (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 31/03/20 alle ore 22:39:00