137031-56-2

Usage

Uses

Used in Pharmaceutical Industry:
Litebamine is used as a precursor for the synthesis of Litebamine N-homologues for their anti-acetylcholinesterase activity. This activity is significant in the development of drugs that can potentially treat conditions related to the cholinergic system, such as Alzheimer's disease and other cognitive disorders.

InChI:InChI=1/C20H21NO4/c1-21-7-6-12-13-5-4-11-8-16(22)17(24-2)9-14(11)18(13)20(25-3)19(23)15(12)10-21/h4-5,8-9,22-23H,6-7,10H2,1-3H3

Upstream product

• 144919-04-0 N-benzylsecoboldine 
• 29268-51-7 N-cyanosecoboldine 
• 55056-93-4 boldine 
• 624720-95-2 8-isopropoxy-9,11,12-trimethoxy-2-methyl-3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-one 
• 50-00-0 formaldehyd 
• 66396-12-1 secoboldine 

Relevant academic research and scientific papers

Litebamine N-homologues: Preparation and anti-acetylcholinesterase activity

Litebamine N-homologues were easily prepared from laurolitsine, generally via three reaction steps (N-alkylation, solvolysis with 1 M NH4OAc under reflux, and the Mannich reaction) in more than 80% overall yield. Among the prepared compounds, N-propyl-, N-isobutyl-, and N-isopropylnorlitebamines exhibited moderate antiacetylcholinesterase activity (IC50 ca. 7.0 μM), while the corresponding N-metho salt of N-propylnorlitebamine showed potent activity (IC50 2.70 μM).

Efficient One-Pot Synthesis of Tetrahydronaphtho[2,1-f]isoquinolines by Using Domino Pictet–Spengler/Friedel–Crafts-Type Reactions

This study describes a facile and efficient one-pot method for the synthesis of a tetrahydronaphtho[2,1-f]isoquinoline alkaloid. An N-protected amino aldehyde biaryl substrate underwent domino Pictet–Spengler/Friedel–Crafts-type cyclization reactions to p

First total syntheses of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines annoretine and litebamine

We describe here the first total synthesis of the two natural 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinolines, annoretine and litebamine, from [2-(2-styrylphenyl)ethyl]methylcarbamic acid ethyl esters. The key steps were the Bischler-Napieralski cyclization

A novel ring cleavage and recyclization of N-cyanomethyl-1,2,3,4-tetrahydroisoquinolinium methiodides: A biomimetic synthesis of litebamine

Treatment of N-cyanomethyl-6-hydroxy-1,2,3,4-tetrahydroisoquinolinium methiodide (1) with NaOMe in MeOH caused C1-N fission and simultaneous recyclization to give 8-hydroxy-5-methoxymethyl-1,2,3,4-tetrahydroisoquinoline (2). By using of the rea

A facile semisynthesis of litEbamine, a novel phenanthrene alkaloid, from boldine via a biogenetical approach

Litebamine was semisynthesized from boldine via a biogenetical approach. Main reactions include Von Braun reaction, exhaustive benzylation and Hofmann degradation in one pot, and the Mannich reaction.