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Yakugaku Zasshi. 2017;137(10):1255-1263. doi: 10.1248/yakushi.17-00142.

Total Syntheses of Multi-substituted Carbazole Alkaloids and Phenolic Related Compounds, and Evaluation of Their Antioxidant Activities.

[Article in Japanese]

Author information

1
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University.

Abstract

This review describes the syntheses and antioxidant activities of carbazole alkaloids carquinostatin A, carbazomadurin A and carbazomadurin B and their related carbazoles. The key step was an allene-mediated electrocyclic reaction involving an indole [b]-bond for the construction of a highly substituted carbazole ring. Antioxidant activities of 3-oxygenated and 3,4-dioxygenated carbazole alkaloids and their related carbazoles were comprehensively evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate) (ABTS)+ radical scavenging assays, and cupper reducing power. Furthemore, the antioxidant activities of simple phenolic carbazoles were evaluated by DPPH and ABTS+ radical scavenging assays. After this, bond dissociation energies (BDE) and highest occupied molecule orbital energy levels (EHOMO) of a series of phenolic carbazoles, including phenolic carbazole alkaloids, were also calculated and then examined for correlation with their antioxidant activities. The phenolic carbazole core possessing a hydroxyl group at the 1-, 3-, 6-, or 8-positions could play an important role in the antioxidant activity of carbazole alkaloids. The results suggest that these compounds could serve as useful clues for designing and developing novel antioxidants.

KEYWORDS:

allene-mediated electrocyclic reaction; antioxidant activity; carbazole alkaloid; total synthesis

PMID:
28966267
DOI:
10.1248/yakushi.17-00142
[Indexed for MEDLINE]
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