A Convenient On-Site Oxidation Strategy for the N-hydroxylation of Melanostatin Neuropeptide using Cope Elimination

In this work, a convenient synthetic protocol for the unprecedented N-hydroxylation of proline residue in Melanostatin (MIF-1) neuropeptide is reported. This methodology is grounded on the incorporation of N-(cyanoethyl)prolyl residue followed by on-site oxidation by Cope elimination with m-chloroperbenzoic acid, exploring the unrecognized dual role of the cyanoethyl group as an effective N-protecting group under peptide synthesis conditions and as a suitable leaving group during the chemoselective on-site N-oxidation. Following this protocol N-hydroxy-MIF-1 is obtained with 78% global yield from N-(cyanoethyl)-L-proline. This synthetic approach opens a new avenue for access to N-hydroxylated Melanostatin analogs with direct application in neurochemistry and Parkinson’s research.

In situ control of photochromic behavior through dual photo-isomerization using cobaloxime complexes with a spiropyran derivative and 2-cyanoethyl ligands

The lifetime of colored species of spiropyran derivatives increased significantly after the 2-cyanoethyl group was photoisomerized to the 1-cyanoethyl group on exposure to visible light.

Control of the photochromic behavior of cobaloxime complexes with salicylidene-3-aminopyridine and 2-cyanoethyl groups by dual photoisomerization

The lifetime of colored species of photochromic derivatives significantly changed after the photoisomerization of the 2-cyanoethyl group.

3-(2,3-Dioxoindolin-1-yl)propanenitrile

The asymmetric unit of the title compound, C11H8N2O2, contains two independent molecules (AandB). Each molecule is build up from fused five- and six-membered rings with the former linked to a cyanoethyl group. The indoline ring and two carbonyl O atoms of each molecule are nearly coplanar, with the largest deviations from the mean planes being 0.0198 (9) (moleculeA) and 0.0902 (9) Å (moleculeB), each by a carbonyl O atom. The fused ring system is nearly perpendicular to the mean plane passing through the cyanoethyl chains, as indicated by the dihedral angles between them of 69.72 (9) (moleculeA) and 69.15 (9)° (moleculeB). In the crystal, molecules are linked by C—H...O and π–π [intercentroid distance between inversion-related indoline (A) rings = 3.6804 (7) Å] interactions into a double layer that stacks along thea-axis direction.