Abstract

This review describes the biological activity and synthesis of structurally and biologically significant isoindoloindolone compounds. The various synthetic reports are mainly described under two headings based on use of palladium chemistry or the Wittig reaction as the key step for the construction of the indole or isoindole ring. Other methods are included in the miscellaneous approaches.

Highlights

  • This heterocyclic structural motif is yet to be revealed in any natural product, it has already received a position of major importance as a bioactive compound

  • The derivatives of isoindoloindolone are well known for their specific bioactivity profiles

  • Isoindoloindolone 1 is used as a precursor in the synthesis of 2-aryl-5-nitroindoles as NorA efflux pump inhibitors.[8,9]

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Summary

Biological Activity

The derivatives of isoindoloindolone are well known for their specific bioactivity profiles. Isoindoloindolone derivatives are reported as potent ligands of MT3.5 The third melatonin binding site, MT3, is an enzyme, quinone reductase-2 and not a usual seven transmembrane domains receptor. Hydroxyisoindoloindolone derivative 2a has subnanomolar affinity for the melatonin binding site MT3. Compounds 2c and 2d exhibit inhibitory potency for topoisomerase-II comparable to that of etoposide.[6,7] Compound 2e shows moderate binding affinity towards human neurokinin-1 (hNK1) receptors in the central nervous system.[1]. The NorA protein is a multidrug resistant efflux in the bacterium Staphylococcus aureus. This has resulted in resistance towards numerous structurally dissimilar antibiotics such as norfloxacin, ethidium bromide, berberine, etc. Isoindoloindolone 1 is used as a precursor in the synthesis of 2-aryl-5-nitroindoles as NorA efflux pump inhibitors.[8,9] Isoindoloindolone 1 exhibit charge-transfer fluorescence with high quantum yields in non polar solvents.[10]

Palladium catalyzed coupling reactions
CH3CHO
COO Me
S OCl2
Conclusions
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