54318-59-1

Usage

Uses

Used in Pharmaceutical Industry:
Mappicine is used as a pharmaceutical compound for its potential therapeutic applications. As a derivative of camptothecin, mappicine may exhibit similar anticancer properties, making it a candidate for further research and development in the treatment of various types of cancer.
Used in Drug Synthesis:
Mappicine is used as a starting material for the synthesis of other bioactive compounds. Its structural similarities to camptothecin allow for the development of novel drugs with potential applications in cancer treatment and other therapeutic areas.

References

Govindacharietal.,l. Chem. Soc., Perkin !, 1215 (1974)

InChI:InChI=1/C19H18N2O2/c1-3-17(22)14-9-16-18-13(10-21(16)19(23)11(14)2)8-12-6-4-5-7-15(12)20-18/h4-9,17,22H,3,10H2,1-2H3

Upstream product

• 192189-64-3 6-Bromo-1-(tert-butyl-diphenyl-silanyl)-4-((S)-1-hydroxy-propyl)-3-methyl-1H-pyridin-2-one 
• 192189-65-4 6-Bromo-4-((S)-1-hydroxy-propyl)-3-methyl-1H-pyridin-2-one 
• 201597-93-5 (E)-4-(3-Methoxymethyl-quinolin-2-yl)-4-oxo-but-2-enoic acid ethyl ester 
• 54934-04-2 2-Carbomethoxy-3-brommethylchinolin 
• 53821-46-8 methyl 3-methylquinoline-2-carboxylate 
• 92513-28-5 3-methyl-2-quinolinecarboxylic acid 
• 55822-01-0 7-(1-acetoxy-propyl)-8-methyl-11H-indolizino[1,2-b]quinolin-9-one 
• 54352-77-1 (+/-)-mappicine 
• 340128-74-7 (4S)-[diisopropyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorooctyl)silanyloxypropyl]-2-methoxyl-3-methyl-6-trimethylsilanylpyridine 
• 305816-10-8 (S)-1-(2-Methoxy-3-methyl-6-trimethylsilanyl-pyridin-4-yl)-propan-1-ol 
• 227455-97-2 cis-Δ^19,20-20-O-acetylmappicine 
• 227455-96-1 trans-Δ^19,20-20-O-acetylmappicine 
• 340128-80-5 7-{1-[(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyl)-diisopropyl-silanyloxy]-propyl}-8-methyl-11H-indolizino[1,2-b]quinolin-9-one 
• 54318-60-4 (S)-mappicine acetate 

Downstream Products

• 55854-89-2 8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one 

Relevant academic research and scientific papers

The first conversion of camptothecin to (S)-mappicine by an efficient chemoenzymatic method

Camptothecin has been converted for the first time to (S)-mappicine via mappicine ketone, which is the sole product of the microwave irradiation of camptothecin. Baker's yeast reduction of mappicine ketone yielded (S)- mappicine in high optical purity.

Quasiracemic synthesis: Concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine

The concept of quasiracemic synthesis is introduced and illustrated with syntheses of both enantiomers of pyridovericin (whose absolute configuration is assigned as R) and mappicine. Like racemic synthesis, quasiracemic synthesis provides both enantiomers in a single synthetic sequence; however, separation tagging is used to ensure that quasiracemic mixtures can be analyzed, separated, and identified on demand. Fluorous tags of differing chain lengths are used to tag two enantiomeric starting materials. The resulting quasienantiomers are mixed to make a quasiracemate, which is then treated like a true racemate in successive steps of the synthesis. Fluorous chromatography is used to separate, or demix, the final quasiracemate into its two components, which are then detagged to provide (true) enantiomeric products. Quasiracemic synthesis is portrayed as the first and simplest of a series of mixture synthesis techniques based on separation tagging, and the prospects for using other types of separation tags are briefly evaluated.

Chemoenzymatic synthesis of (S)- and (R)-mappicines and their analogues

The natural alkaloids, camptothecin and mappicine ketone were converted into racemic mappicine which on treatment with vinyl acetate in presence of the lipase Candida cylindracea (CCL) afforded (S)-mappicine acetate and (R)-mappicine. The acetate was chemically hydrolysed to (S)-mappicine. 9-Methoxycamtpothecin and 9-methoxymappicine ketone were similarly converted into (S)- and (R)-9-methoxymappicines.

Enantioselective synthesis of (S)- and (R)-mappicines and their analogues

The naturally occurring alkaloids, camptothecin and mappicine ketone were converted to racemic mappicine acetate which was enantioselectively hydrolyzed to (S)- and (R)-mappicines in high optical purity using baker's yeast and a lipase, Amano PS. Treatment of the racemic acetate with baker's yeast afforded (S)-mappicine while with Amano PS yielded (R)-mappicine. 9- Methoxycamptothecin and 9-methoxymappicine ketone underwent similar conversion to (S)- and (R)-9-methxymappicines.

Chemoenzymatic Transformation of the Natural Antitumour Alkaloid 20-O-Acetylcamptothecin to Mappicine Ketone and (S)-Mappicine

Microwave irradiation of the naturally occurring antitumour alkaloid 20-O-acetylcamptothecin affords trans- and cis-Δ19,20-20-O-acetylmappicine and 17-acetylmappicine ketone. The first two products when treated with dilute alkali yield mappicine ketone, an antiviral lead compound, which is reduced with baker's yeast to form another natural alkaloid, (S)-mappicine. Baker's yeast treatment of the major product, trans-Δ19,20-20-O-acetylmappicine produces both mappicine ketone as well as (S)-mappicine. The last compound is converted to mappicine ketone by oxidation with pyridinium chlorochromate.

Total synthesis of nothapodytine b and (-)-mappicine

Concise total syntheses of naturally occurring nothapodytine B (1, mappicine ketone) and ( - )-mappicine (3) are detailed. The approach is based on the implememation of a room-temperature, inverse electron demand Diels-Alder reaction of the N-sulfonyl-1-aza-1.3-butadiene 11 for assemblage of a pyridone 1) ring precursor central to the structure. A Friedlander condensation is utilized for constructing the AB ring system of 1 and 3. An acid-catalyzed reaction sequence is used to accomplish a deprotection with subsequent ring-closure for introduction of the C ring in a single step.

Synthesis of (S)-Mappicine and mappicine ketone via radical cascade reaction of isonitriles

(S)-Mappicine (2) and mappicine ketone (1) have been prepared from methylacetoacetate (4) by a strategy featuring a radical cascade reaction of an isonitrile as the key step. The introduction of the hydroxy group of (S)- mappicine occurred with moderate selectivity through asymmetric hydroxylation.