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“Free of Base” Sulfa-Michael Addition for Novel o-carboranyl-DL-cysteine Synthesis
| Content Provider | MDPI |
|---|---|
| Author | Laskova, Julia Kosenko, Irina Ananyev, Ivan Stogniy, Marina Sivaev, Igor Bregadze, Vladimir |
| Copyright Year | 2020 |
| Description | The sulfa-Michael addition reaction was applied for the two-step synthesis of o-carboranyl cysteine 1-HOOCCH(NH2)CH2S-1,2-C2B10H11 from the trimethylammonium salt of 1-mercapto-o-carborane and methyl 2-acetamidoacrylate. To avoid the decapitation of o-carborane into its nido-form, the “free of base” method under mild conditions in a system of two immiscible solvents toluene-H2O was developed. The replacement of H2O by 2H2O resulted in carboranyl-cysteine containing a deuterium label at the α-position of the amino acid 1-HOOCCD(NH2)CH2S-1,2-C2B10H11. The structure of the protected o-carboranyl cysteine was determined by single-crystal X-ray diffraction. The obtained compounds can be considered as potential agents for the Boron Neutron Capture Therapy of cancer. |
| Starting Page | 1133 |
| e-ISSN | 20734352 |
| DOI | 10.3390/cryst10121133 |
| Journal | Crystals |
| Issue Number | 12 |
| Volume Number | 10 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2020-12-11 |
| Access Restriction | Open |
| Subject Keyword | Crystals Organic Chemistry Boron Chemistry O-carborane Sulfa-michael Addition Reaction Cysteine Boron Neutron Capture Therapy O-carborane Decapitation Labeled Compound |
| Content Type | Text |
| Resource Type | Article |
