55854-89-2Relevant articles and documents
Conversion of camptothecins to mappicine ketones using silica gel supported sodium hydrogen sulfate catalyst
Das, Biswanath,Madhusudhan
, p. 3321 - 3325 (2000)
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
Preparation of mappicine ketones from camptothecins: Chemistry of the camptothecin E ring
Fortunak,Mastrocola,Mellinger,Wood
, p. 5763 - 5764 (1994)
Camptothecin and its analogs are thermolyzed at 150-200 °C to yield mappicine ketone derivatives by loss of carbon dioxide from the α- hydroxylactone.
Two efficient methods of the conversion of camptothecin to mappicine ketone, an antiviral lead compound
Das, Biswanath,Madhusudhan,Kashinatham
, p. 431 - 432 (1998)
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.
Traceless solid-phase synthesis of mappicine ketone library via multiple chemoselective palladium-catalyzed reactions on benzenesulfonate linker
Tsukamoto, Hirokazu,Suzuki, Risako,Kondo, Yoshinori
experimental part, p. 2005 - 2010 (2009/04/10)
We report here a solid-phase synthesis of a library of mappicine ketone, a leading antiviral compound with activity against herpes viruses and human cytomegalovirus. The synthesis is based on multiple chemoselective palladium-catalyzed reactions involving
Total synthesis of nothapodytine B and (±)-mappicine
Chavan, Subhash P.,Sivappa, Rasapalli
, p. 3941 - 3943 (2007/10/03)
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.
Synthesis of (+/-) mappicine and mappicine ketone
Henegar, Kevin E.,Baughman, Ted A.
, p. 601 - 605 (2007/10/03)
Mappicine and mappicine ketone are camptothecin analogs of interest as antiviral agents. A novel synthesis of these compounds is described using a Friedlander condensation. The requisite ketone is prepared via a regioselective ortho-directed metallation/a
Total synthesis of mappicine ketone (nothapodytine B) by means of sulfur-directed 5-exo-selective aryl radical cyclization onto enamides
Kato, Issei,Higashimoto, Masayuki,Tamura, Osamu,Ishibashi, Hiroyuki
, p. 7983 - 7989 (2007/10/03)
Enamides 5, on treatment with Bu3SnH-AIBN, underwent aryl radical cyclization in a 5-exo manner to give 1-[bis(phenylthio)methyl]dihydroisoindoles 6, which were partially desulfurized with Bu3SnH-AIBN to give 1-mono(phenylthio)methyl
A Modular Approach to Oxoindolizino Quinolines: Efficient Synthesis of Mappicine Ketone (Nothapodytine B)
Raolji, Gajendra B.,Garcon, Stephanie,Greene, Andrew E.,Kanazawa, Alice
, p. 5059 - 5061 (2007/10/03)
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.
2-Pyridones from cyanoacetamides and enecarbonyl compounds: Application to the synthesis of nothapodytine B
Carles, Lionel,Narkunan, Kesavaram,Penlou, Sebastien,Rousset, Laurence,Bouchu, Denis,Ciufolini, Marco A.
, p. 4304 - 4308 (2007/10/03)
The condensation of an enone or enal with cyanoacetamide derivatives and t-BuOK furnishes either 3-cyano-2-pyridones or 3-unsubstituted-2-pyridones, depending on whether the reaction is carried out in the presence or in the absence of O2. In the first case, in situ oxidation of Michael-type intermediates takes place; in the second case, the products result from "decyanidative aromatization" of such intermediates. A one-step synthesis of 3-alkyl-2-pyridones has been devised on the basis of decyanative union of an enone/enal and a 2-alkylcyanoacetamide. The new reaction forms the centerpiece of an unusually concise synthesis of nothapodytine B (mappicine ketone).
Preparation of camptothecin and nothapodytine derivatives
-
, (2008/06/13)
The invention concerns the preparation of nothapodytine or camptothecin derivatives which consists in causing 4-ethyl 2methyl hepta-2,4-dienoic acid act on a 3-aminomethyl 2-bromo quinoline derivative (III) wherein R1and R2are H or R1is a halogen atom or alkyl, R2is a O—CO—X radical as defined for the camptothecin derivatives; or R1and R2are defined for the known camptothecin derivatives or represent protected radicals or radicals easily convertible into the radicals R1and R2, to obtain the quinoline derivative (IV); adding to the resulting quinoline derivative (2-methoxy carbonyl vinyl) tributyltin in the presence of a complex of palladium and triphenylarsin to obtain the quinoline derivative (V); cyclizing the resulting quinoline derivative to obtain the tetracyclic derivative (VI); then in subjecting said derivative to an ozonolysis followed by treatment with dimethyl sulphide to obtain the tetracyclic derivative (VII); saponification followed by decarboxylation in oxidising conditions of the resulting tetracyclic derivative to obtain the nothopodytine derivative (VIII); then optionally transforming the resulting derivative into a camptothecin derivative or into a mappicine derivative.
