Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass
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 oc...
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| Format: | Article |
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MDPI AG
2017-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/12/2210 |
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| author | Konstantin I. Galkin Fedor A. Kucherov Oleg N. Markov Ksenia S. Egorova Alexandra V. Posvyatenko Valentine P. Ananikov |
| author_facet | Konstantin I. Galkin Fedor A. Kucherov Oleg N. Markov Ksenia S. Egorova Alexandra V. Posvyatenko Valentine P. Ananikov |
| author_sort | Konstantin I. Galkin |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-11T08:39:16Z |
| format | Article |
| id | doaj.art-667f85153d2c44038f91507982982e54 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T08:39:16Z |
| publishDate | 2017-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-667f85153d2c44038f91507982982e542022-12-22T01:14:17ZengMDPI AGMolecules1420-30492017-12-012212221010.3390/molecules22122210molecules22122210Facile Chemical Access to Biologically Active Norcantharidin Derivatives from BiomassKonstantin I. Galkin0Fedor A. Kucherov1Oleg N. Markov2Ksenia S. Egorova3Alexandra V. Posvyatenko4Valentine P. Ananikov5Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaZelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaZelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaZelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaInstitute of Gene Biology, Russian Academy of Sciences, Vavilova Str. 34/5, 119334 Moscow, RussiaZelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, RussiaReductive 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.https://www.mdpi.com/1420-3049/22/12/2210biomass2,5-diformylfuranreductive aminationnorcantharidindiastereoselectivityDiels–Alder reaction |
| spellingShingle | Konstantin I. Galkin Fedor A. Kucherov Oleg N. Markov Ksenia S. Egorova Alexandra V. Posvyatenko Valentine P. Ananikov Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass Molecules biomass 2,5-diformylfuran reductive amination norcantharidin diastereoselectivity Diels–Alder reaction |
| title | Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass |
| title_full | Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass |
| title_fullStr | Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass |
| title_full_unstemmed | Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass |
| title_short | Facile Chemical Access to Biologically Active Norcantharidin Derivatives from Biomass |
| title_sort | facile chemical access to biologically active norcantharidin derivatives from biomass |
| topic | biomass 2,5-diformylfuran reductive amination norcantharidin diastereoselectivity Diels–Alder reaction |
| url | https://www.mdpi.com/1420-3049/22/12/2210 |
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