Meisenheimer Rearrangement of Azetopyridoindoles. VIII. Synthesis and Antiviral Activities of 12-Carbaeudistomin Analogs

Takushi KURIHARA; Yasuhiko SAKAMOTO; Tetsuya KIMURA; Hirofumi OHISHI; Shinya HARUSAWA; Ryuji YONEDA; Tatsuo SUZUTANI; Masanobu AZUMA

doi:10.1248/cpb.44.900

Takushi KURIHARA, Yasuhiko SAKAMOTO, Tetsuya KIMURA, Hirofumi OHISHI, Shinya HARUSAWA, Ryuji YONEDA, Tatsuo SUZUTANI, Masanobu AZUMA

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Keywords: eudistomin, 12-carbaeudistomin, antiviral activity, Meisenheimer rearrangement, structure-activity relationship, MNDO calculation

JOURNAL FREE ACCESS

1996 Volume 44 Issue 5 Pages 900-908

DOI https://doi.org/10.1248/cpb.44.900

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Abstract

Eudistomins, isolated from the colonial tunicate Eudistoma olivaceum, have been a synthetic target due to their strong antiviral activity against Herpes simplesx virus (HSV-1) and activities against certain types of tumors in vivo. In order to examine the structure-activity relationship of eudistomins, 12-carbaeudistomin analogs were synthesized and their activities against influenza A and B virus, HSV-1, HSV-2 and human cytomegalovirus were investigated. Among them, racemic 6-methoxy-12-carbaeudistomin showed similar activity to (-)-debromoeudistomin K, synthesized as a control compound.

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