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Titolo:
Facile macrocyclizations to beta-turn mimics with diverse structural, physical, and conformational properties
Autore:
Park, C; Burgess, K;
Indirizzi:
Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA Texas A&M Univ College Stn TX USA 77842 t Chem, College Stn, TX 77842 USA
Titolo Testata:
JOURNAL OF COMBINATORIAL CHEMISTRY
fascicolo: 3, volume: 3, anno: 2001,
pagine: 257 - 266
SICI:
1520-4766(200105/06)3:3<257:FMTBMW>2.0.ZU;2-N
Fonte:
ISI
Lingua:
ENG
Soggetto:
NERVE GROWTH-FACTOR; SOLID SUPPORT SYNTHESIS; PROTEIN-PROTEIN INTERACTIONS; 14-MEMBERED MACROCYCLES; SNAR METHODOLOGY; PEPTIDE MIMETICS; HIGHLY EFFICIENT; FACTOR RECEPTORS; PHASE SYNTHESIS; AMINO-ACIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
41
Recensione:
Indirizzi per estratti:
Indirizzo: Burgess, K Texas A&M Univ, Dept Chem, POB 30012, College Stn, TX 77842 USATexas A&M Univ POB 30012 College Stn TX USA 77842 TX 77842 USA
Citazione:
C. Park e K. Burgess, "Facile macrocyclizations to beta-turn mimics with diverse structural, physical, and conformational properties", J COMB CHEM, 3(3), 2001, pp. 257-266

Abstract

On-resin SNAr reactions were performed to prepare the macrocyclic p-turn mimics 1a-n (Scheme 1 and Table I). These reactions occurred more efficiently than completely analogous macrocyclization reactions that do not involve an iodinated aromatic electrophile. The synthesis was also modified to allow introduction of an alkyne via a solid-phase Sonogashira reaction (giving compound 2, Scheme 2) and an aryne via a solid-phase Suzuki reaction (giving compound 3, Scheme 2). Conformational analyses of three illustrative compounds, i.e., 1i, 2, and 3, were performed using a combination of NMR, circular dichroism, and computer-aided molecular simulation methods. Overall, the preferred conformations of all three molecules tended to be type-I-like beta -turns, but for compound 3 interaction of the electron cloud of the aryl substituent with the oxygen lone pairs seems to cause differences in the preferred orientation of the turn frameworks. This study illustrates how iodinated electrophiles can be used in solid-phase SNAr reactions to increasethe molecular and conformational diversity in a library.

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Documento generato il 01/12/20 alle ore 22:53:06