Synchrotron X-ray powder diffraction data of LASSBio-1515: A new N-acylhydrazone derivative compound

Costa, Fanny N.; Braz, Delson; Ferreira, Fábio Furlan; Silva, T.F. da; Barreiro, Eliezer J.; Lima, Lı́dia Moreira; Colaço, Marcos V.; Kuplich, L.; Barroso, R.C.

doi:10.1016/j.radphyschem.2013.02.014

Cited by 5 publications

(1 citation statement)

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“…Aiming to determine unambiguously the relative configuration and conformation of the cyclohexyl- N -acylhydrazone derivative 10 X-ray powder diffraction was performed [ 25 ]. The results indicated that in the solid phase the compound is an E diastereoisomer (-N=CH-), having equatorial substitution of the cyclohexyl ring, with an antiperiplanar conformation of the hydrogen amide and oxygen atom of the carbonyl group ( Figure 5 ).…”

Section: Resultsmentioning

confidence: 99%

Novel Orally Active Analgesic and Anti-Inflammatory Cyclohexyl-N-Acylhydrazone Derivatives

et al. 2015

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The N-acylhydrazone (NAH) moiety is considered a privileged structure, being present in many compounds with diverse pharmacological activities. Among the activities attributed to NAH derivatives anti-inflammatory and analgesic ones are recurrent. As part of a research program aiming at the design of new analgesic and anti-inflammatory lead-candidates, a series of cyclohexyl-N-acylhydrazones 10–26 were structurally designed from molecular modification on the prototype LASSBio-294, representing a new class of cycloalkyl analogues. Compounds 10–26 and their conformationally restricted analogue 9 were synthetized and evaluated as analgesic and anti-inflammatory agents in classical pharmacologic protocols. The cyclohexyl-N-acylhydrazones 10–26 and the cyclohexenyl analogue 9 showed great anti-inflammatory and/or analgesic activities, but compound 13 stood out as a new prototype to treat acute and chronic painful states due to its important analgesic activity in a neuropathic pain model.

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Section: Resultsmentioning

confidence: 99%