1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribo

Details 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribo 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribo

1973-08-21

1977-02-15

Gotts, Lewis

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

Organic compounds

Carbohydrates or derivatives

424180, C02H 902

Patent

active

040083624

ABSTRACT:
An 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR1## wherein R is a hydrogen atom or .beta.-D-ribofuranosyl group of the formula ##STR2## and R.sub.3 is hydroxyl, amino-NH.sub.2 or acylamino group --NHR.sub.4 in which R.sub.4 is an acyl group, and n is a whole number of 1 to 4, may be produced by subjecting the corresponding O-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin of the formula ##STR3## or its hydroxyl-masked and maino-masked form, to the action of a basic medium to produce an acyl-migration product of the formula: ##STR4## and, optionally converting the amino-masking groups into hydrogen atoms and also the hydroxyl-masking group into hydroge atom in a known manner if said amino-masking groups and said hydroxyl-masking groups are present in the acyl-migration product. The 1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin produced is characterized by its useful activity inhibitory to the growth of bacteria resistant to the parent substance neamine or ribostamycin.

REFERENCES:
patent: 3781268 (1973-12-01), Kawaguchi
patent: 3792037 (1974-02-01), Kawaguchi et al.
patent: 3925354 (1975-12-01), Umezawa et al.
Adams et al., Org. Reactions, vol. 12, pp. 172-173, 1962, Wiley & Sons, Inc., New York.
Moore et al., Azaserine," Synthetic Studies I J.A.C.S., vol. 76, pp. 2884, (1954).
Sidgwick, N.V. The Org. Chem. of Nitrogen, pp. 105-106, 1966, Clarendon Press, Oxford.
Royals, E. E., Adv. Org. Chem., p. 600, 1954, Prentice-Hall, Inc., Englewood Cliff, N. J.
Fujisawa et al., "Aminoglycoside Antibiotics" J. of Antibiotics, vol. 27, No. 9, 1974, pp. 677-681.

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