The Chan–Evans–Lam <i>N</i>‑Arylation of 2‑Imidazolines

<i>N</i>-Arylation of 2-imidazolines with arylboronic acids promoted by copper­(II) acetate in DMSO provides an attractive alternative to the earlier reported transition metal-catalyzed approaches employing (hetero)­aryl halides as it taps into the vast reagent space of commercially available boronic acids and proceeds at ambient temperature. Many of the resulting compounds are distinctly lead-like, thus positioning the method developed well within the toolbox of lead-oriented synthesis

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Bicyclic Piperazine Mimetics of the Peptide β‑Turn Assembled via the Castagnoli–Cushman Reaction

5-Oxopiperazine-2-carboxamides and respective carboxylic acids (obtained by the Castagnoli–Cushman reaction of protected iminodiacetic anhydride) were converted into <i>cis</i>- and <i>trans</i>-configured bicyclic piperazines containing two stereogenic centers. The latter are not only well-established mimetics of peptide β-turn but also attractive, high-F_sp3 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

Library of diversely substituted 2-(quinolin-4-yl)imidazolines delivers novel non-cytotoxic antitubercular leads

<p>A novel library based on quinolin-4-ylimidazoline core was designed to incorporate a general quinoline antimicrobial pharmacophore. A synthesis of the well-characterized library of 36 compounds was achieved using the Pd-catalyzed Buchwald–Hartwig-type imidazoline arylation chemistry developed earlier. Compounds were tested for biological activity and were found to possess no antimalarial activity. However, the library delivered two promising antitubercular leads, which are non-cytotoxic and can be further optimized with respect to antimycobacterial potency.</p