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Titolo:
Preparation of a 990-member chemical compound library of hydantoin- and isoxazoline-containing heterocycles using multipin technology
Autore:
Park, KH; Ehrler, J; Spoerri, H; Kurth, MJ;
Indirizzi:
Univ Calif Davis, Dept Chem, Davis, CA 95616 USA Univ Calif Davis Davis CA USA 95616 Davis, Dept Chem, Davis, CA 95616 USA Novartis Crop Protect AG, CH-4002 Basel, Switzerland Novartis Crop ProtectAG Basel Switzerland CH-4002 02 Basel, Switzerland
Titolo Testata:
JOURNAL OF COMBINATORIAL CHEMISTRY
fascicolo: 2, volume: 3, anno: 2001,
pagine: 171 - 176
SICI:
1520-4766(200103/04)3:2<171:POA9CC>2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
SOLID-PHASE SYNTHESIS; ANTICONVULSANT ACTIVITIES; SODIUM-CHANNEL; DERIVATIVES; SUBSTITUENTS; BINDING;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
21
Recensione:
Indirizzi per estratti:
Indirizzo: Kurth, MJ Univ Calif Davis, Dept Chem, Davis, CA 95616 USA Univ Calif Davis Davis CA USA 95616 t Chem, Davis, CA 95616 USA
Citazione:
K.H. Park et al., "Preparation of a 990-member chemical compound library of hydantoin- and isoxazoline-containing heterocycles using multipin technology", J COMB CHEM, 3(2), 2001, pp. 171-176

Abstract

The development of a useful chemistry for the construction of polyfunctional heterocycles-first through solution and solid phase (resins) and then library production via SynPhase crowns-is reported. Bead-based synthetic workwas done on Merrifield resin where treatment with benzylamine in the presence of DBU followed by reaction with 4-chloromethylbenzoyl chloride afforded amide-linked resin 9. Finally, TFA . NH2-polystyrene macro crowns were derivatized with 4-(hydroxymethyl)benzoic acid to afford pin 14 which was coupled with Boc-protected amino acid 2 in the presence of DIC to deliver pin 15. Deprotection and reaction with phenyl isocyanate afforded urea functionalized pin 17 which underwent 1,3-dipolar cycloaddition reaction to give pin 19. Finally, compound 20 was obtained with moderate diastereoselectivity (20:21::8:1) by the reaction of pin 19 with a catalytic amount of Et3N.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/03/20 alle ore 01:58:14