7-(diphenylmethyl)oxy-9a-methoxymitosane

Details 7-(diphenylmethyl)oxy-9a-methoxymitosane 7-(diphenylmethyl)oxy-9a-methoxymitosane

1990-03-08

1991-12-24

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514410, C07D48714, A61K 3140

Patent

active

050754548

ABSTRACT:
7-(Diphenylmethyl)oxy-9a-methoxymitosane is a novel intermediate for conversion into 7-amino and 7-oxy-9a-methoxymitosanes and is also useful for inhibiting mammalian tumor growth. The compound is prepared by reacting 7-hydroxy-9a-methoxymitosane with diazodiphenylmethane. In a preferred reaction, the compound is prepared from mitomycin C via 7-hydroxy-9a-methoxymitosane without drying (water removal). The intermediate is advantageously converted to the very effective anti-tumor agent 7-[2-(4-nitrophenyldithio)ethylamino]-9a-methoxymitosane in unexpectedly high yields using a two step process where the first step constitutes conversion to 7-[2-(2-pyridyldithio)ethylamino]-9a-methoxymitosane or 7-[2-(3-nitro-2-pyridyldithio)ethylamino]-9a-methoxymitosane.

REFERENCES:
Black T. H., Aldrichimica Acta, vol. 16, No. 1, 1983 Elks, J. (ed.), Recent Advances in the Chemistry of .beta.-Lactam Antibiotics, Special Pub. No. 28, The Chemical Society, 139-144 (1977).
Fieser & Fieser, Reagents for Organic Synthesis, vol. 1, p. 191 (1967).
Fieser & Fieser, Reagents for Organic Synthesis, vol. 1, pp. 338-339 (1967).
The Merck Index, 11th ed., p. 473 (1989).
Sami, S. M. et al., J. Med. Chem. 32, 703-708 (1989).

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