Enantioselectivity in cardioprotection induced by (S)- (-)-2,2-dimethyl-N-(4'-acetamido-benzyl)-4-spiromorpholone-chromane.
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.
Rapposelli
Simona
S
Dipartimento di Scienze Farmaceutiche, Universita di Pisa, Pisa, Italy. rappsi@farm.unipi.it
Calderone
Vincenzo
V
Cirilli
Roberto
R
Digiacomo
Maria
M
Faggi
Cristina
C
La Torre
Francesco
F
Manganaro
Mariaelisa
M
Martelli
Alma
A
Testai
Lara
L
D000818:Animals; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D002316:Cardiotonic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D066298:In Vitro Techniques; D008958:Models, Molecular; D008968:Molecular Conformation; D017202:Myocardial Ischemia / Q000188:drug therapy / Q000473:pathology / Q000503:physiopathology; D015425:Myocardial Reperfusion; D051381:Rats; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C550368:2,2-dimethyl-N-(4'-acetamidobenzyl)-4-spiromorpholonechromane; D001578:Benzopyrans; D002316:Cardiotonic Agents; D013141:Spiro Compounds