6873-09-2

Usage

Uses

Used in Pharmaceutical Industry:
Epiberberine is used as a chemopreventive agent for the inhibition of colon tumor formation. It targets the enzyme cyclooxygenase-2 (COX-2), which is abundantly expressed in colon cancer cells, thereby preventing the growth and progression of cancerous cells.

InChI:InChI=1/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1

Upstream product

• 72744-54-8 5-bromo-benzo[1,3]dioxole-4-carbaldehyde 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 51665-54-4 dihydroepiberberine 
• 19716-60-0 8-oxo-epiberberine 

Relevant academic research and scientific papers

Method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control

The invention discloses a method for synthesizing benzophenanthridine and protoberberine alkaloids through modular diversity regulation and control. The method comprises the following steps: improving a substituent group of a high-iodine salt leaving group, generating pyridine alkyne under the action of relatively mild potassium tert-butoxide, and carrying out [4 + 2] cycloaddition reaction on the pyridine alkyne and diene to obtain polysubstituted isoquinoline ring precursor compounds. Ring opening and aromatization of the isoquinoline ring precursor are realized by developing a novel iridium-catalyzed cross-coupling method, polysubstituted isoquinoline ring compounds with connecting capacity are efficiently synthesized, and then the polysubstituted isoquinoline ring compounds are coupled with a high-activity polysubstituted cyclic boric acid to obtain 3-aryl isoquinoline high-grade intermediates. Through application of two different chemical principles, regulation and control of the 3-aryl isoquinoline high-grade intermediates are realized, and benzophenanthridine and protoberberine alkaloids are modularly, diversely and efficiently synthesized.

A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps

A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.