55854-89-2

Basic information

• Product Name: MAPPICINE KETONE
• Synonyms: MAPPICINE KETONE;NOTHAPODYTINE B
• CAS NO: 55854-89-2
• Molecular Formula: C₁₉H₁₆N₂O₂
• Molecular Weight: 304.34
• Mol File: 55854-89-2.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 591.7°Cat760mmHg
• Flash Point: 311.6°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 5.68E-14mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: MAPPICINE KETONE(CAS DataBase Reference)
• NIST Chemistry Reference: MAPPICINE KETONE(55854-89-2)
• EPA Substance Registry System: MAPPICINE KETONE(55854-89-2)

Safety Data

• Hazardous Substances Data: 55854-89-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H16N2O2/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/h4-9H,3,10H2,1-2H3

Upstream product

• 54352-77-1 (+/-)-mappicine 
• 201597-96-8 1-[2-Methoxy-6-(3-methoxymethyl-quinolin-2-yl)-3-methyl-pyridin-4-yl]-propan-1-one 
• 31456-25-4 camptothecin 
• 192189-64-3 6-Bromo-1-(tert-butyl-diphenyl-silanyl)-4-((S)-1-hydroxy-propyl)-3-methyl-1H-pyridin-2-one 
• 192189-66-5 6-Bromo-4-((S)-1-hydroxy-propyl)-3-methyl-1-prop-2-ynyl-1H-pyridin-2-one 
• 192189-65-4 6-Bromo-4-((S)-1-hydroxy-propyl)-3-methyl-1H-pyridin-2-one 
• 1197040-29-1 phenyl isocyanate 
• 201597-93-5 (E)-4-(3-Methoxymethyl-quinolin-2-yl)-4-oxo-but-2-enoic acid ethyl ester 
• 201597-94-6 (E)-4-[(Z)-Methanesulfonylimino]-4-(3-methoxymethyl-quinolin-2-yl)-but-2-enoic acid ethyl ester 
• 181699-44-5 dimethyl [2-[3-(methoxymethyl)quinolin-2-yl]-2-oxoethyl]phosphonate 
• 181699-56-9 3-Methoxymethyl-quinoline-2-carboxylic acid methyl ester 
• 529-23-7 o-aminobenzaldehyde 
• 54934-04-2 2-Carbomethoxy-3-brommethylchinolin 
• 53821-46-8 methyl 3-methylquinoline-2-carboxylate 

Downstream Products

• 714251-46-4 5-benzoyloxymappicine ketone 
• 54318-59-1 (S)-mappicine 

Relevant articles and documents

Concise synthesis of mappicine ketone and (±)-mappicine

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Conversion of camptothecins to mappicine ketones using silica gel supported sodium hydrogen sulfate catalyst

Silica gel supported sodium hydrogen sulfate (NaHSO4.SiO2) catalyst has been utilized for the conversion of camptothecin and 9-methoxycamptothecin to mappicine ketone, an antiviral lead compound and its analogue, 9-methoxymappicine k

Two efficient methods of the conversion of camptothecin to mappicine ketone, an antiviral lead compound

Two simple and efficient methods for the conversion of the naturally occurring alkaloid, camptothecin to mappicine ketone, an antiviral lead compound, have been described. The first method involved the treatment of camptothecin with borontrifluoride etherate and the second method utilised the microwave irradiation of the alkaloid.

Total synthesis of nothapodytine B and (±)-mappicine

A novel, efficient total synthesis of the naturally occurring antiviral nothapodytine B (2, mappicine ketone) is reported. The approach is based on the successful implementation of the Johnson orthoester rearrangement of allylic alcohol 7 for assembly of a pyridone D ring precursor with the necessary functionalities. Nothapodytine B is converted into mappicine by NaBH4 reduction.

A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)

A general route to oxoindolizino quinolines, such as nothapodytine A, mappicine, camptothecin, and several chemotherapeutic derivatives, is illustrated by the synthesis of the antiviral natural product from Nothapodytes foetida, mappicine ketone (R1 = R4 H, R2 = CH3, R3 = COC2H5). A wide range of new camptothecinoids should now be readily available for biological testing.