Chemical modification of antitumor alkaloids, 20(S)-camptothecin and 7-ethylcamptothecin: Reaction of the E-lactone ring portion with hydrazine hydrate

Article abstract of DOI:10.1248/cpb.41.971

The structure of the N-amino pyridone (4a) obtained by the reaction of camptothecin (1a) with hydrazine was determined by X-ray crystallography. A mixture of 7-ethylcamptothecin (1b) and hydrazine hydrate was stirred at room temperature, and the hydrazide (2b) was isolated as its diacetate 2c. Treatment of the 17-O-acetyl amide (5a) with hydrazine gave 1b (74% yield) and the N-amino lactam 6 (11% yield). Compounds with bulky acyl groups, 5c-e, gave 6 in modest yields. The N-amino lactam 6 was smoothly dehydrated into the pyridone 4d by refluxing in hydrazine hydrate.

Full text of DOI:10.1248/cpb.41.971

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