$$N$$ N -Polybenzylated alicyclic 1,2-diamines: cytotoxicity and G1 phase arrest in cancer cell line

Abstract

Cytotoxicity in the μM range was observed in cancer cell lines treated with N,N,N',N'-tetrabenzyl-4,5-diamino-2-cyclopentenone. Cell cycle analysis on HeLa cells showed a clear G1 phase arrest. A preliminary SAR on structural analogs was performed in order to identify the pharmacophores.

Synthesis of trans-4,5-Bis-dibenzylaminocyclopent-2-enone from Furfural Catalyzed by ErCl3·6H2O

“…Additionally, 1 H NMR spectroscopy is used to identify the product. The direct transformation of furfural 1 , to trans- 4,5-bis-diaminocyclopent-2-enone, has been reported for several amines (mainly secondary) using different catalysts. − On the basis of the recently reported method using the catalyst erbium­(III) chloride hexahydrate, which is moderately expensive and has low toxicity, the procedure was adapted to the teaching laboratory environment to address the following needs: (1) use of a substrate that permits isolation of the product in high yield and without need of column chromatography, (2) completion of an experiment that is feasible during one laboratory session (3 h), and (3) use of a readily available and environmentally friendly solvent (published experiment uses ethyl lactate as a solvent). From this study, reproducible results were observed using dibenzylamine (2.…”

“…Although a wide range of methodologies for the synthesis of functionalized cyclopentenones exist, the Lewis acid catalyzed transformation of furfural using Sc­(OTf) 3 , Dy­(OTf) 3 , AlCl 3 , ErCl 3 ·6H 2 O, p- toluenesulfonamide, BF 3 ·OEt 2 , or a heteronuclear 3d/Dy­(III) cluster is especially efficient and practical. Moreover, the proposed mechanism for this transformation is very interesting for educational purposes. , On the basis of this facile transformation of furfural ( 1 ) into cyclopentenones with Lewis acids, an undergraduate laboratory experiment, catalyzed by ErCl 3 ·6H 2 O, was developed using the environmentally friendly solvent ethanol (Scheme ).…”

“…The trans-4,5-diamino functionality has mainly been explored as a synthetic intermediate for the synthesis of Agelastatin A, 5 pactamycin, 6 and 2,4-bifunctionalized cyclopentenones. 7 Although a wide range of methodologies for the synthesis of functionalized cyclopentenones exist, the Lewis acid catalyzed transformation of furfural using Sc(OTf) 3 , Dy(OTf) 3 , 8 AlCl 3 , 7 ErCl 3 •6H 2 O, 9 p-toluenesulfonamide, 10 BF 3 •OEt 2 , 11 or a heteronuclear 3d/Dy(III) cluster 12 is especially efficient and practical. Moreover, the proposed mechanism for this transformation is very interesting for educational purposes.…”