Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass.

Konstantin Galkin,Valentine Ananikov,Oleg Markov,Alexandra Posvyatenko,Ksenia Egorova,Fedor Kucherov

doi:10.3390/molecules22122210

Abstract

Reductive amination of 2,5-diformylfuran (DFF) was used to implement the transition from bio-derived 5-hydroxymethylfurfural (HMF) to pharmaceuticals. The synthesized bis(aminomethyl)furans were utilized as building blocks for the construction of new derivatives with structural cores of naturally occurring biologically active compounds. Using the one-pot procedure, which included the Diels–Alder reaction followed by hydrogenation of the double bond, bio-derived analogues of the anticancer drug norcantharidin were obtained. The cyclization process was diastereoselective, and resulted in the formation of tricyclic products with the endo configuration. Analysis of cytotoxycity for the resulting tricyclic amine-containing compounds showed an increase of anticancer activity as compared with the unsubstituted norcantharimide.

Highlights

Plant biomass is the largest renewable source of carbohydrates, with a mass of about 1011 tons of carbon per year [1]
The most promising approach to the synthetic utilization of biomass involves the catalytic conversion of carbohydrates to molecular building blocks, which are often defined as platform chemicals [2,3]. 5-Hydroxymethylfurfural (HMF) is one of the most important platform chemicals, as it has many possibilities, especially in the fields of biofuels [4,5,6,7,8], biomaterials production [9,10,11,12], and fine chemical applications [13,14,15]
We report the reductive amination of 2,5-diformylfuran (DFF) to connect

Summary

Introduction

Plant biomass is the largest renewable source of carbohydrates, with a mass of about 1011 tons of carbon per year [1]. 5-Hydroxymethylfurfural (HMF) is one of the most important platform chemicals, as it has many possibilities, especially in the fields of biofuels [4,5,6,7,8], biomaterials production [9,10,11,12], and fine chemical applications [13,14,15]. N-alkyl and the formation of the mixture of 10-endo and 10-exo products with a diastereomeric ratio of 4:1, respectively Both diastereomers were isolated by column chromatography and characterized spectroscopically. The diastereomeric configuration was determined by 1H-NMR and NOE substituent, and the formation of the mixture of 10-endo and 10-exo products with a diastereomeric ratio of2017, 4:1,22,respectively. Both diastereomers were isolated by column chromatography and Molecules of 10 characterized spectroscopically. The diastereomeric configuration was determined by 1 H-NMR and NOE experiments

Methods

Results

Conclusion