Aralkyl and aralkenyl glycosides as inhibitors of antigen-specif

Details Aralkyl and aralkenyl glycosides as inhibitors of antigen-specif Aralkyl and aralkenyl glycosides as inhibitors of antigen-specif

1983-10-11

1985-11-19

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 41, 536 172, 536 175, 536 22, 536 53, C07H 506

Patent

active

045543496

ABSTRACT:
The invention disclosed herein relates to novel 1-deoxyglycosides, preferably 1-deoxy-D-mannopyranosides and 1-deoxy-L-rhamnopyranosides, having in the 1-position of the pyranose ring an aralkylthio/aralkenylthio, aralkyloxy/aralkenyloxy or aralkanoylamino/aralkenoylamino substituent; and to novel processes for preparing these 1-substituted-1-deoxyglycosides starting with the corresponding tetra-O-acetylglycopyranosyl bromide or amine. The 6-hydroxy group of 1-substituted-1 deoxyglycopyranosides can also be replaced by other functional groups. These aralkylthio/aralkenylthio, aralkyloxy/aralkenyloxy and aralkanoylamino/aralkenoylamino 1-deoxyglycosides are potent inhibitors of antigen-specific T-cell proliferation and are also useful as inhibitors of delayed-type hypersensitivity reactions.

REFERENCES:
patent: 4228274 (1980-10-01), Ponpipom et al.
Muchmore et al., Macrophage Regulation Immunity, 1980, pp. 505-517.

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