51145-61-0Relevant articles and documents
LIPOXYGENASE INHIBITORS
-
, (2021/10/02)
Various embodiments of the present disclosure are directed to compounds having Formula (I), Formula (IA), Formula (IB), Formula (IC), Formula (ID), Formula (IE), and/or pharmaceutically acceptable salts thereof. The compounds can be suitable for inhibiting lipoxygenases, and/or treating associated diseases, such as Alzheimer's disease. In some embodiments, the compounds may be administered to a patient as part of a pharmaceutical formulation.
Synthesis method for (R)-3-amino-1,2,3,4-tetrahydrocarbazole
-
, (2016/10/08)
The invention discloses a synthesis method for a Ramatroban intermediate (R)-3-amino-1,2,3,4-tetrahydrocarbazole.The synthesis method includes the steps that 1,4-cyclohexanedione monoethylene acetal and phenylhydrazine are subjected to aldehyde ketone amine condensation, then cyclization is conducted to obtain 3,3-vinyl dioxo-1,2,4,9-tetrahydrocarbazole-3-ketone, then protecting groups are removed to obtain 1,2,4,9-tetrahydrocarbazole-3-ketone, 1,2,4,9-tetrahydrocarbazole-3-ketone and O-hydroxylamine hydrochloride react to obtain oxime ether, and oxime ether is subjected to low-temperature chiral selective reduction to directly obtain (R)-3-amino-1,2,3,4-tetrahydrocarbazole.A new synthesis route of the important intermediate (R)-3-amino-1,2,3,4-tetrahydrocarbazole of medicine Ramatroban is provided.The synthesis method is simple and convenient, operation conditions are mild, the reaction yield is high, an amplification reaction can be conducted, and the synthesis method is applied to industrial production.
Asymmetric chemoenzymatic synthesis of ramatroban using lipases and oxidoreductases
Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
, p. 4842 - 4848 (2012/07/31)
A chemoenzymatic asymmetric route for the preparation of enantiopure (R)-ramatroban has been developed for the first time. The action of lipases and oxidoreductases has been independently studied, and both were found as excellent biocatalysts for the production of adequate chiral intermediates under very mild reaction conditions. CAL-B efficiently catalyzed the resolution of (±)-2,3,4,9-tetrahydro-1H-carbazol-3-ol that was acylated with high stereocontrol. On the other hand, ADH-A mediated bioreduction of 4,9-dihydro-1H-carbazol-3(2H)-one provided an alternative access to the same enantiopure alcohol previously obtained through lipase-catalyzed resolution, a useful synthetic building block in the synthesis of ramatroban. Inversion of the absolute configuration of (S)-2,3,4,9-tetrahydro-1H-carbazol-3-ol has been identified as a key point in the synthetic route, optimizing this process to avoid racemization of the azide intermediate, finally yielding (R)-ramatroban in enantiopure form by the formation of the corresponding amine and the convenient functionalization of both exocyclic and indole nitrogen atoms.
