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Molecules 2017, 22(12), 2210; https://doi.org/10.3390/molecules22122210

Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass

1
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia
2
Institute of Gene Biology, Russian Academy of Sciences, Vavilova Str. 34/5, 119334 Moscow, Russia
3
Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Ministry of Health of Russian Federation, Samory Mashela Str., 117198 Moscow, Russia
*
Author to whom correspondence should be addressed.
Received: 9 November 2017 / Revised: 30 November 2017 / Accepted: 7 December 2017 / Published: 12 December 2017
(This article belongs to the Special Issue Platform Chemical: Hydroxymethylfurfural (HMF))
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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. View Full-Text
Keywords: biomass; 2,5-diformylfuran; reductive amination; norcantharidin; diastereoselectivity; Diels–Alder reaction biomass; 2,5-diformylfuran; reductive amination; norcantharidin; diastereoselectivity; Diels–Alder reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Galkin, K.I.; Kucherov, F.A.; Markov, O.N.; Egorova, K.S.; Posvyatenko, A.V.; Ananikov, V.P. Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass. Molecules 2017, 22, 2210.

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