γ‑Turn Mimicry with Benzodiazepinones and Pyrrolobenzodiazepinones Synthesized from a Common Amino Ketone Intermediate

Abstract

To investigate diazepinone analogues as γ-turn mimics, seven 1,4-benzodiazepin-2-ones <b>6</b> and fourteen pyrrolo­[1,2-<i>d</i>]­[1,4]­benzodiazepin-6-ones <b>4</b> and <b>5</b> were synthesized from 1-(2-aminophenyl)­pent-4-en-1-one (<b>7</b>). Acylation of aniline <b>7</b> with <i>N</i>-Boc-amino acids, olefin oxidation, Boc removal, and intramolecular Paal–Knorr condensation gave <b>4</b> and <b>5</b>. Alternatively, Boc removal prior to oxidation gave benzodiazepinones <b>6</b>, which were converted to <b>4</b> by ozonolysis and cyclization. Comparison of dihedral angle values for the amino acid component from X-ray analyses of <b>4g</b>, <b>5f</b>, and <b>6f</b> and related diazepinones has catalogued the manner by which ring substituents affect the component’s ability to mimic the central residues of γ-turns

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