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Issue 1, 2015
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Structural characterization of LASSBio-1289: a new vasoactive N-methyl-N-acylhydrazone derivative

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Abstract

LASSBio-1289 compound has been found to promote intense vasodilation and antihypertensive activity. It is an innovative compound, without structural similarities to the three main classes of calcium antagonists (1,4-dihydropyridines, benzothiazepines and phenylalkylamines) commonly used. A complete knowledge of the structure, including stereochemistry, is essential to lead optimization in drug discovery. For this reason, in this work we determined the crystal structure of this novel vasoactive N-methyl-N-acylhydrazone derivative by means of X-ray powder diffraction data and an ab initio simulating annealing approach, allowing us to observe the relative configuration E of the imine double bond and its conformation as well as its most relevant intermolecular interactions. These findings were also checked by a FTIR analysis and confirmed in solution by NMR. The compound crystallized under a monoclinic crystal system with space group P21/c and unit cell parameters a = 14.5118(3) Å, b = 12.1374(2) Å, c = 7.5498(1) Å, β = 91.113(1)°, V = 1329.53(4) Å3, Z = 4, Z′ = 1 and ρcalc = 1.44042(4) g cm−3. Moreover, a crystal morphology prediction, experimentally compared with SEM inferred images, allowed a direct comparison of the microcrystalline habit and quality, allowing a study of the potential solvent effect on the crystal growth.

Graphical abstract: Structural characterization of LASSBio-1289: a new vasoactive N-methyl-N-acylhydrazone derivative

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Publication details

The article was received on 03 Oct 2014, accepted on 21 Oct 2014 and first published on 21 Oct 2014


Article type: Paper
DOI: 10.1039/C4CE02011A
Citation: CrystEngComm, 2015,17, 165-173
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    Structural characterization of LASSBio-1289: a new vasoactive N-methyl-N-acylhydrazone derivative

    J. A. P. Sato, F. N. Costa, M. D. da Rocha, E. J. Barreiro, C. A. M. Fraga, F. Punzo and F. F. Ferreira, CrystEngComm, 2015, 17, 165
    DOI: 10.1039/C4CE02011A

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