Approximately 60 derivatives of anguidin were prepared for evaluation of antitumor activities. Positions 3, 4, 8-10, and 15 were modified, and the resultant derivatives were screened against P-388 leukemia. It was found that introduction of the C3-keto and C3,C8-diketo groups markedly improved the antileukemic activity, whereas epoxidation of the C9-C10 double bond or oxidation of the C15 position diminished its activity. Selected derivatives were further tested in the L1210, B16, Lewis lung, Colon 36, and Colon 38 tumor lines. Among these compounds, 4 beta, 15-diacetoxyscirpene-3,8-dione (54) and 4 beta-(chloroacetoxy)-15-acetoxyscirpene-3,8-dione (55) were found to be most active in various tumors. Inhibitory action of several analogues on protein synthesis was also examined using H-HeLa cells.
1. Aus gasförmigem Chlordioxyd und Fluor läßt sich unter ge‐eigneten Bedingungen, z. B. Chlordioxyd‐Druckenivon etwa 25 mm oder darunter, Fluordrucken von etwa 50 mm und Zusatz mehrerer hundert Millimeter inerten Gases bei einem Gesamtdruck von 1 Atm. und Temperaturen um 0°C, eine Verbindung von der Zusammensetzung ClO2F darstellen.
Growing cells of Fusarium oxysporum f.sp. vasinfectum (ATCC 7808) formed 3-acetoxyscirpene-4,15-diol from anguidine (4,15-diacetoxyscirpene-3-ol) by way of the intermediates triacetoxyscirpene, 3,4-diacetoxyscirpene-15-ol and 3,15-diacetoxyscirpene-4-ol. The new 3-acetoxy analog was found to be less active than anguidine and the two other monoacetoxy derivatives when tested against a series of fungal strains and against HeLa cells in vitro.
Resting cells of Streptomyces griseus, Mucor mucedo, and a growing culture of Acinetobacter calcoaceticus when mixed with compounds related to 12,13epoxytrichothec-9-ene-4,8,15-diacetoxy-3a-ol(anguidine) produced a series of derivatives that were either partially hydrolyzed or selectively acylated. These derivatives showed marked differences in activities as assayed by antifungal and tissue culture cytotoxicity tests.
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