Synthesis and Anti-HSV Activity of A-Ring-Deleted Mappicine Ketone Analog

Natural Product‐Like Combinatorial Libraries

“…Reductive amination of resin bound aldehyde with primary amines gave secondary amines 195, which, by coupling with sulfonyl chlorides afforded the sulfonamide products 196, after cleaveage from the resin (Figure 50 (198) 203 and its ketone analogue nothapodytine B (199) 204 are two tryptophan-derived alkaloids with antiviral activity against herpes viruses (HSV) and human cytomegalovirus (HCMV). 205 Curran and Frutos 206 reported the generation of a 128-member library of mapicine analogues (64 racemates) and a 48 member library of nothapodytine B analogues, by solution phase parallel synthesis, based on a radical cascade annulation. The radical cascade strategy to mappicine is summarized in Figure 51.…”

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

“…Mappicine ketone, present in small amounts in Nothapodytes foetida (a plant found in India), [1] and formed by thermolysis of camptothecin, [8] displays strong, selective activity against herpes viruses (HSV-1 and HSV-2, including Acyclovirresistant forms) and human cytomegalovirus. [9,10] The synthesis of 1 a began with the formation of the known adduct 4 a by cycloaddition of the carbonyl ylide derived from 3 with methyl acrylate (Scheme 2). [11] This multistep sequence proceeded smoothly and in high yield when catalyzed by rhodium(ii) acetate.…”

X-Ray Diffraction and Theoretical Approach to the Molecular Structure of (E)-2-(2-(1,3-dioxoisoindolin-2-yl)-1-(3-phenyl-3-methylcyclobutyl)ethylidene) hydrazine carboxamide

“…Many compounds containing the isoindolinone skeleton have shown antiviral, antileukemic, antiinflammatory, antipsychotic and antiulcer properties [1,2]. Isoindolinones are useful for the synthesis of various drugs and naturally occurring compounds [3,4].…”