128432-38-2

Basic information

• Product Name: (+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol
• CAS NO: 128432-38-2
• Molecular Weight: 187.241
• Mol File: 128432-38-2.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol(128432-38-2)
• EPA Substance Registry System: (+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol(128432-38-2)

Safety Data

• Hazardous Substances Data: 128432-38-2(Hazardous Substances Data)

Upstream product

• 13482-22-9 4-hydroxycyclohexanone 
• 100-63-0 phenylhydrazine 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 51145-61-0 1,2,3,4-tetrahydrocarbazol-3-one 
• 54621-12-4 1,2,4,9-tetrahydrospiro[3H-carbazole-3,2*-[1,3]doxolane] 

Downstream Products

• 34154-31-9 3-hydroxy-1,2,3,4-tetrahydrocarbazole p-toluenesulphonate ester 
• 51145-61-0 1,2,3,4-tetrahydrocarbazol-3-one 
• 868984-45-6 (+/-)-benzyl 2,3,4,9-tetrahydro-1H-carbazol-3-yl-carbamate 
• 1374648-21-1 (S)-benzyl 2,3,4,9-tetrahydro-1H-carbazol-3-yl-carbamate 
• 116650-12-5 4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide 
• 118699-38-0 (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide 
• 134525-56-7 (S)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide 
• 141307-19-9 (R)-methyl 3-[3-(4-fluorophenylsulfonamido)-3,4-dihydro-1H-carbazol-9(2H)-yl]propanoate 
• 116650-33-0 (3R)-2,3,4,9-tetrahydro-1H-carbazol-3-amine 
• 116650-34-1 (3S)-2,3,4,9-tetrahydro-1H-carbazol-3-amine 
• 116650-36-3 (R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide 
• 116650-37-4 (S)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide 
• 116649-85-5 ramatroban 
• 61894-99-3 2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine 

Relevant articles and documents

Asymmetric chemoenzymatic synthesis of ramatroban using lipases and oxidoreductases

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.

TRICYCLIC CYTOPROTECTIVE COMPOUNDS

Compounds of formula (I): in which: X is a group of formula >CR1R2 or >SO2; Y is a group of formula >NH or >CR1R2; Z is a group of formula >C=O or >CH2 or a direct bond; R1 hydrogen and R2 is hydrogen, carboxy or hydroxy; or R1 and R2 together represent an oxo group, a methylenedioxy group or a hydroxyimino group; R3 is hydrogen or lower alkyl; R4 represents two hydrogen atoms, or an oxo or hydroxyimino group; R5 is hydrogen, lower alkyl or halogen; R6 is hydrogen, lower alkoxy or carboxy; R7 and R8 are each hydrogen, lower alkyl or halogen; and pharmaceutically acceptable salts and esters thereof can be used for the treatment or prophylaxis of acute or chronic neurodegenerative diseases or conditions such as Alzheimer’s Disease, Parkinson’s Disease, Huntington’s Chorea, Multiple Sclerosis or the sequelae to acute ischaemic events such as heart attack, stroke or head injury and for protection against ischaemic damage to tissues of peripheral organs.