23367-61-5

Usage

Uses

Used in Pharmaceutical Applications:
Cherylline is used as a potential medicinal compound for its weak acetylcholinesterase inhibitory activity, which can be beneficial in the treatment of conditions related to the nervous system.
Used in Cancer Research:
Cherylline is used as a compound with mild activity against Molt 4 lymphoid and non-tumoral fibroblastic LMTK cells, which can be valuable in the study and development of cancer treatments.
Used in Cardiovascular Research:
Due to its moderate hypotensive effect on arterial pressure, cherylline is used in research aimed at understanding and developing treatments for cardiovascular conditions, such as hypertension.
Used in DNA Interaction Studies:
Cherylline's slight interaction with DNA makes it a compound of interest in studies exploring the interactions between small molecules and genetic material, which can have implications for gene regulation and the development of new therapeutic strategies.

InChI:InChI=1/C17H19NO3/c1-18-9-12-7-16(20)17(21-2)8-14(12)15(10-18)11-3-5-13(19)6-4-11/h3-8,15,19-20H,9-10H2,1-2H3/t15-/m0/s1

Upstream product

• 96444-12-1 (S)-7-(benzyloxy)-4-(4-(benzyloxy)phenyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 612483-13-3 (4S)-5-hydroxymethyl-4-[1-(4-hydroxyphenyl)-2-methylaminoethyl]-2-methoxyphenol 
• 612483-12-2 (1S,1'R)-5-benzyloxy-2-{1-(4-benzyloxyphenyl)-2-[methyl-(1'-phenylethyl)amino]ethyl}-4-methoxybenzaldehyde 
• 96405-80-0 (S)-3,9-Bis-benzyloxy-2-methoxy-7,12-dihydro-5H-6,12-methano-dibenzo[c,f]azocine 6-oxide 
• 96405-81-1 (R)-7-Benzyloxy-4-(4-benzyloxy-2-formyl-phenyl)-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 96405-83-3 (S)-7-Benzyloxy-4-(4-benzyloxy-phenyl)-6-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 96405-79-7 3,9-dibenzyloxy-2-methoxytetrahydro-6,12-methanodibenzazocine 
• 96444-11-0 (S)-3,9-Bis-benzyloxy-2-methoxy-7,12-dihydro-5H-6,12-methano-dibenzo[c,f]azocine 

Downstream Products

• 23367-60-4 (S)-6,7-dimethoxy-4-(4-methoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

A new synthesis of (+)- and (-)-cherylline.

A new and concise synthesis of enantiopure antipodes of alkaloid cherylline has been devised. The synthetic strategy relies upon the reduction of a diversely and polyprotected diarylenamine bearing a chiral auxiliary. Separation of diastereopure intermediates, concomitant deprotections and intramolecular reductive amination complete the synthesis of the natural (S)-enantiomer and of the unnatural (R)-configured antipode.

A New Route to (-)-Cherylline via a Regiocontrolled Polonovski-type Reaction as the Key Step

A facile and efficient synthesis of (-)-cherylline (1) was accomplished in 46percent overall yield starting from the readily accessible (12S)-(-)-3,9-dibenzoyloxy-2-methoxy-tetrahydro-6,12-methanodibenzazocine (4) via a regiocontrolled Polonovski-typ