Synthesis of spiro-pyrrolizidine: Crystal structure and anticancer activity

Journal of Molecular Structure
2024.0

Abstract

A novel spiro - pyrrolizidine[2 ' -{[3,5-bis(benzyloxy)phenyl]carbonyl}-1 ' -(4-ethoxyphenyl)-1,1 ' ,2,2 ' ,5 ' ,6 ' ,7 ' 7 ' a-octahy- drospiro[indole-3,3 ' -pyrrolizine]-2-one (compound 1 ) was synthesized via 1,3-dipolar cycloaddition of by refluxing 1-(3,5-bis(benzyloxy)phenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one with isatin and L-proline . The structure was successfully elucidated by determination of single-crystal structures. The spiro-pyrrolizidine ( 1 ) crystallized in the triclinic centrosymmetric space group P1. The compound 1 exhibits significant anticancer activity on MDA-MB 231 and HCT-116 cell lines with an IC 50 values of 61.07 +/- 0.98 mu M and 62.5 +/- 70 mu M respectively.

Knowledge Graph

Similar Paper

Synthesis of spiro-pyrrolizidine: Crystal structure and anticancer activity
Journal of Molecular Structure 2024.0
Synthesis of new spirooxindole-pyrrolothiazole derivatives: Anti-cancer activity and molecular docking
Bioorganic & Medicinal Chemistry 2017.0
Discovery of pyrazolone spirocyclohexadienone derivatives with potent antitumor activity
Bioorganic & Medicinal Chemistry Letters 2020.0
Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line
Bioorganic & Medicinal Chemistry Letters 2013.0
Synthesis and QSAR study of novel cytotoxic spiro[3H-indole-3,2′(1′H)-pyrrolo[3,4-c]pyrrole]-2,3′,5′(1H,2′aH,4′H)-triones
European Journal of Medicinal Chemistry 2012.0
Synthesis of novel spiro[pyrazolo[4,3- d ]pyrimidinones and spiro[benzo[4,5]thieno[2,3- d ]pyrimidine-2,3′-indoline]-2′,4(3H)-diones and their evaluation for anticancer activity
Bioorganic & Medicinal Chemistry Letters 2017.0
Synthesis and anticancer activity of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of α-santonin
European Journal of Medicinal Chemistry 2013.0
Synthesis of novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens
Bioorganic & Medicinal Chemistry Letters 2008.0
A facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines
European Journal of Medicinal Chemistry 2009.0
Facile and diastereoselective synthesis of 3,2′-spiropyrrolidine-oxindoles derivatives, their molecular docking and antiproliferative activities
Bioorganic & Medicinal Chemistry Letters 2015.0