TY - JOUR

T1 - Bicyclic Piperazine Mimetics of the Peptide β-Turn Assembled via the Castagnoli-Cushman Reaction

AU - Usmanova, Liliia

AU - Dar'In, Dmitry

AU - Novikov, Mikhail S.

AU - Gureev, Maxim

AU - Krasavin, Mikhail

PY - 2018/5/18

Y1 - 2018/5/18

N2 - 5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli-Cushman reaction of protected iminodiacetic anhydride) were converted into cis- and trans-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-Fsp3 cores for drug design in general. The methodology was applied to the preparation of ring-expanded version of bicyclic piperazines not described in the literature.

AB - 5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli-Cushman reaction of protected iminodiacetic anhydride) were converted into cis- and trans-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-Fsp3 cores for drug design in general. The methodology was applied to the preparation of ring-expanded version of bicyclic piperazines not described in the literature.

KW - SOLID-SUPPORTED SYNTHESIS

UR - http://www.scopus.com/inward/record.url?scp=85046550017&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/bicyclic-piperazine-mimetics-peptide-%CE%B2turn-assembled-via-castagnolicushman-reaction

U2 - 10.1021/acs.joc.8b00811

DO - 10.1021/acs.joc.8b00811

M3 - Article

AN - SCOPUS:85046550017

VL - 83

SP - 5859

EP - 5868

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 10

ER -