Resolution and absolute stereochemistry of 6,7-dimethoxy-4-phenyl- 1,2,3,4-tetrahydroisoquinoline. The crystal structure of the R-hydrochloride salt form.
dc.contributor.author | Mondeshka D. | |
dc.contributor.author | Angelova I. | |
dc.contributor.author | Stensland B. | |
dc.contributor.author | Werner P.E. | |
dc.contributor.author | Ivanov C. | |
dc.date.accessioned | 2024-07-10T14:27:02Z | |
dc.date.accessioned | 2024-07-10T14:46:53Z | |
dc.date.available | 2024-07-10T14:27:02Z | |
dc.date.available | 2024-07-10T14:46:53Z | |
dc.date.issued | 1992-01-01 | |
dc.description.abstract | Stereospecific multistep synthesis and resolution of 6,7-dimethoxy-4- phenyl-1,2,3,4-tetrahydroisoquinoline (3) has been achieved from its racemic base. The absolute configurations of the optical antipodes converted into their hydrochloride salt forms have been determined by X-ray diffractometric analysis, thus permitting assignment of the antipodes as the (+)-(4R)-3 and (-)-(4S)-3 enantiomers. The crystal structures of the two enantiomers are related as mirror images and only the (4R)-3.HCl form has been fully determined by three-dimensional X-ray diffraction. In the solid state, the carbon atoms of the two methoxy groups deviate slightly from the benzene-ring plane and the chirally oriented phenyl substituent is almost perpendicularly tilted out of conjugation with the isoquinoline system. Examination of the enantiomers in several biochemical tests for 5-HT, NE and DA uptake inhibition-activity revealed an exclusive preference for the (4S)-enantiomer. These results are in accord with previous suggestions that the S-configurational state of the 4-phenyl substituent is important for biological activity. | |
dc.identifier.doi | 10.3891/acta.chem.scand.46-0054 | |
dc.identifier.issn | 0904-213X | |
dc.identifier.scopus | SCOPUS_ID:0026444687 | en |
dc.identifier.uri | https://rlib.uctm.edu/handle/123456789/51 | |
dc.language.iso | en | |
dc.source.uri | https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0026444687&origin=inward | |
dc.title | Resolution and absolute stereochemistry of 6,7-dimethoxy-4-phenyl- 1,2,3,4-tetrahydroisoquinoline. The crystal structure of the R-hydrochloride salt form. | |
dc.type | Article | |
oaire.citation.issue | 1 | |
oaire.citation.volume | 46 |