6533b820fe1ef96bd127a3d1
RESEARCH PRODUCT
Scalable (Enantioselective) Syntheses of Novel 3-Methylated Analogs of Pazinaclone, (S)-PD172938 and Related Biologically Relevant Isoindolinones
Antonia Di MolaGiorgia NicastroLorenzo SerusiRosanna FilosaMario WaserAntonio Massasubject
heterocyclesisoindolinonesChemistry (miscellaneous)asymmetric synthesisOrganic ChemistryDrug Discoveryheterocycles; asymmetric synthesis; isoindolinonesMolecular MedicinePharmaceutical SciencePhysical and Theoretical ChemistryAnalytical Chemistrydescription
Herein, we report the application of an efficient and practical K2CO3 promoted cascade reaction of 2-acetylbenzonitrile in the synthesis of novel 3-methylated analogs of Pazinaclone and PD172938, belonging to isoindolinones heterocyclic class bearing a tetrasubstituted stereocenter. Organocatalytic asymmetric synthesis of the key intermediate and its transformation into highly enantioenriched 3-methylated analog of (S)-PD172938 was also developed. These achievements can be of particular interest also for medicinal chemistry, since the methyl group is a very useful structural modification in the rational design of new and more effective bioactive compounds.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2022-09-01 | Molecules |