Abstract
This work aimed to determine the enantioselectivity in cardioprotection induced by the racemic mixture of the "archetype" 1a of a new class of spirocyclic-benzopyran derivatives. The racemate was resolved by HPLC and the absolute configuration was accomplished by a combined strategy based on single-crystal X-ray diffraction and circular dichroism methods. The (S)-(-)-1a enantiomer, evaluated for its anti-ischemic activity, showed significant cardioprotective effects, whereas the (R)-(+)-1a enantiomer was completely lacking in anti-ischemic effects.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Benzopyrans / chemical synthesis
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Benzopyrans / chemistry*
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Benzopyrans / therapeutic use
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Cardiotonic Agents / chemical synthesis
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Cardiotonic Agents / chemistry*
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Cardiotonic Agents / therapeutic use
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Chromatography, High Pressure Liquid
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Circular Dichroism
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Crystallography, X-Ray
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In Vitro Techniques
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Models, Molecular
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Molecular Conformation
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Myocardial Ischemia / drug therapy
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Myocardial Ischemia / pathology
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Myocardial Ischemia / physiopathology
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Myocardial Reperfusion
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Rats
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Spiro Compounds / chemical synthesis
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Spiro Compounds / chemistry*
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Spiro Compounds / therapeutic use
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Stereoisomerism
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Structure-Activity Relationship
Substances
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2,2-dimethyl-N-(4'-acetamidobenzyl)-4-spiromorpholonechromane
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Benzopyrans
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Cardiotonic Agents
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Spiro Compounds