17807-64-6

Usage

References

Johns et al., Austral. J. Chem., 23, 363 (1970)

Upstream product

• 61659-87-8 (+/-)-N-trifluoroacetylwilsonirine 
• 39945-40-9 (+/-)-norglaucine 
• 371196-16-6 (6aS)-4,5,6a,7-tetrahydro-1,2,9,10-tetramethoxy-6H-dibenzo[de,g]quinoline-6-carbaldehyde 
• 5890-18-6 (+)-norboldine 
• 39945-43-2 (±)-wilsonirine 
• 39945-37-4 oxoaporphine 
• 371196-15-5 N-formyl-laurolitsine 
• 169304-60-3 (1R,4aR,2'S)-1,2,3,4,4a,7-hexahydro-7-oxo-4a-(2'-phenylpropionyloxy)-2-trifluoroacetyl-1-veratrylisoquinoline 
• 61659-86-7 (+/-)-N-trifluoroacetylnorcodamine 
• 169437-86-9 (R)-(-)-6-trifluoroacetylwilsonirine 
• 169304-65-8 (1S,4aS,2'S)-1,2,3,4,4a,7-hexahydro-7-oxo-4a-(2'-phenylpropionyloxy)-2-trifluoroacetyl-1-veratrylisoquinoline 
• 169437-88-1 (S)-(+)-6-trifluoroacetylwilsonirine 
• 50722-33-3 6-formyl-1,2,9,10-tetramethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 
• 128957-80-2 Acetic acid 1-(3,4-dimethoxy-benzyl)-6-methoxy-7-oxo-2-(2,2,2-trifluoro-acetyl)-1,2,3,4,6,7-hexahydro-isoquinolin-6-yl ester 

Relevant academic research and scientific papers

ALKALOIDS OF Corydalis paniculigera

The alkaloid composition of the roots of Corydalis paniculigera Rgl., collected in the flowering phase in the Alai range, has been studied.Chloroform extraction yielded 0.39percent of total alkaloids, from which were isolated wilsonirine, thalicmidine, coclaurine, stylopine, dihydrosanguinarine, sanguinarine, oxosanguinarine, adlumine, adlumidine, bicucculine, sibiricine, protopine, pancorine, and corunnine, and new alkaloids which have been called pancoridine (I) and pancorinine (II).The structures of (I) and (II) have been established on the basis of spectral characteristics and also the production of wilsonirine on their reduction in sulfuric acid.

Semisynthesis and myocardial activity of thaliporphine N-homologues

The N-homologues and optical isomers of thaliporphine (5a), a potent antiarrhythmic agent, were prepared starting from laurolitsine (1), an abundant aporphine present in Phoebe formosana. Treating N-propylnorglaucine with 90% H2SO4 yielded one additional product, an 11-sulfonyl-1,11-anhydroaporphine. Reaction of N-formylnorglaucine (3a) with 90% H2SO4, however, yielded the 9-sulfonyl-seco product as a major product. Treatment of 3a with 98% H2SO4 yielded pancordine (10), which, upon catalytic hydrogenation, yielded (±)-wilsonirine. 1H NMR spectroscopic analysis was applied successfully to monitor the optical purity of the crystalline salt while undertaking optical resolution. Thaliporphine (5a) was demonstrated to possess better positive inotropic and less negative chronotropic effects than the left-hand optical isomer and showed the best activity on rat cardiac tissue among the N-homologues prepared.

APORPHINE AND OXOAPORPHINE COMPOUNDS AND PHARMACEUTICAL USE THEREOF

The invention provides aporphine and oxoaporphine compounds that may be used to manufacture a medicaments for preventing or treating vascular dysfunction resulting in ischemic and metabolic diseases or preventing complications in human and mammal. The isc

Synthesis of optically active aporphine and morphinandienone alkaloids via p-quinol esters

Lead tetraacetate oxidation of N-trifluoroacetylnorcodamine (5) in (S)-(+)-2-phenylpropionic acid gave a diastereomeric mixture of two p-quinol acylates, which were easily separated to enantiomerically pure 6a and 6b. Treatment of the chiral quinol acylates (6a) and (6b) with trifluoroacetic acid in CH2Cl2 at room temperature afforded (1R)-(-)-6-trifluoroacetylwilsonirine (7a) and (1S)-(+)-(7b), respectively. Saponification of 7a and 7b gave rise to (-)-wilsonirine (8a) and its enantiomer (8b), respectively. Similarly, (-)-nordomesticine (12a) and (+)-(12b) were synthesized in enantiomerically pure form from 10a and 10b. On the other hand, acid treatment of 6a and 6b in CH3CN at lower temperature (-30°C) llowed by N-deprotection gave the corresponding normorphinandienones (15a and 15b) as major products, which were transformed to enantiomerically pure (-)-16a and (+)-sebiferine (16b). In a similar sequence of reactions, (+)-amurine (19a) and its enantiomer (19b) were synthesized.

A NOVEL SYNTHESIS OF (+/-)-NORAPORPHINE ALKALOIDS, (+/-)-WILSONIRINE AND (+/-)-NORDOMESTICINE

(+/-)-Wilsonirine (1a) and (+/-)-nordomesticine (1b) were synthesized in moderate yields on acid treatment, followed by alkaline hydrolysis of o-quinolacetates (o-QAs) (3) readily obtained by lead tetraacetate oxidation of (+/-)-N-trifluoroacetyltetrahydr

THE DEMETHYLATION OF APORPHINES WITH SULFURIC ACID

Sulfuric acid at room temperature has been found a useful reagent for interconverting aporphine alkaloids by selective O-demethylation.This was controlled by electronic or steric effects.