4 results match your criteria pyrrolizines bearing

  • Page 1 of 1

Pharmacophore-based virtual screening, synthesis, biological evaluation, and molecular docking study of novel pyrrolizines bearing urea/thiourea moieties with potential cytotoxicity and CDK inhibitory activities.

J Enzyme Inhib Med Chem 2021 Dec;36(1):15-33

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia.

In the current study, virtual screening of a small library of 1302 pyrrolizines bearing urea/thiourea moieties was performed. The top-scoring hits were synthesised and evaluated for their cytotoxicity against three cancer (MCF-7, A2780, and HT29) and one normal (MRC-5) cell lines. The results of the MTT assay revealed potent cytotoxic activities for most of the new compounds (IC = 0. Read More

View Article and Full-Text PDF
December 2021

Brønsted Acid Catalyzed [6 + 2]-Cycloaddition of 2-Vinylindoles with in Situ Generated 2-Methide-2 H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-1 H-pyrrolizines.

Org Lett 2019 01 8;21(2):519-523. Epub 2019 Jan 8.

Institut für Organische Chemie , Universität Leipzig , Johannisallee 29 , 04103 Leipzig , Germany.

We describe herein an organocatalytic, diastereo- and enantioselective [6 + 2]-cycloaddition toward the synthesis of densely substituted 2,3-dihydro-1 H-pyrrolizines bearing three contiguous stereogenic centers which are obtained with good yields, as single diastereomers, and with excellent enantioselectivity. A crucial feature of this one-step process leading to a prominent structural motif in many biologically active natural products is a BINOL-derived phosphoric acid catalyzed reaction of 1 H-pyrrole-2-yl carbinols with 2-vinylindoles via the corresponding hydrogen-bonded chiral 2-methide-2 H-pyrroles. Read More

View Article and Full-Text PDF
January 2019

Cinchona-based primary amine-catalyzed asymmetric cascade aza-Michael-aldol reactions of enones with 2-(1H-pyrrol-2-yl)-2-oxoacetates: synthesis of chiral pyrrolizines with multistereocenters.

J Org Chem 2013 Apr 27;78(7):3306-12. Epub 2013 Feb 27.

Department of Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea.

Cinchona-based primary amine-catalyzed cascade aza-Michael-aldol reactions of α,β-unsaturated ketones with 2-(1H-pyrrol-2-yl)-2-oxoacetates provided highly functionalized chiral pyrrolizines bearing multistereocenters including a chiral quaternary carbon center in good yields (up to 92%) with excellent levels of stereocontrol (90-95% ee, >20:1 dr in all cases). The ketone group in the cascade product was asymmetrically reduced to chiral secondary hydroxyl groups in good yields. Read More

View Article and Full-Text PDF

Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions.

Org Lett 2010 Oct;12(19):4352-5

Department of Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea.

As the first N-centered heteroaromatic nucleophile for organocatalytic cascade reactions, pyrroles underwent the enantio- and diastereoselective organocatalytic cascade conjugate addition-aldol reactions of α,β-unsaturated aldehydes that afford the highly functionalized chiral pyrrolizines bearing three consecutive stereocenters in good yields, high enantioselectivities (90-98% ee), and excellent diastereoselectivities (>20:1 dr in all cases). Read More

View Article and Full-Text PDF
October 2010
  • Page 1 of 1