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Adrian O. Dukes ; Pathum M. Weerawarna ; Allison N. Devitt , et al. JOC,2024,89(12):9110-9117. DOI: 10.1021/acs.joc.4c00781 PubMed ID: 38857432
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Abstract: Inhibition of human ornithine aminotransferase interferes with glutamine and proline metabolism in hepatocellular carcinoma, depriving tumors of essential nutrients. A proposed mechanism-based inhibitor containing a bicyclo[3.1.1]heptanol warhead is reported herein. The proposed inactivation mechanism involves a novel α-iminol rearrangement. The synthesis of the proposed inhibitor features an asymmetric intramolecular Mannich reaction, utilizing a chiral sulfinamide. This study presents a novel approach toward the synthesis of functionalized bicyclo[3.1.1]heptanes and highlights an underutilized method to access enantiopure exocyclic amines.
Purchased from AmBeed: 23761-23-1 ; 1892-57-5 ; 505-23-7
CAS No. : | 505-23-7 | MDL No. : | MFCD00006654 |
Formula : | C4H8S2 | Boiling Point : | - |
Linear Structure Formula : | CH2(SCH2CH2CH2S) | InChI Key : | WQADWIOXOXRPLN-UHFFFAOYSA-N |
M.W : | 120.23 | Pubchem ID : | 10451 |
Synonyms : |
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Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P264-P273-P302+P352-P304+P340-P305+P351+P338-P332+P313-P337+P313 | UN#: | 3335 |
Hazard Statements: | H315-H319-H335-H410-H372 | Packing Group: | Ⅲ |
GHS Pictogram: |
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