2'-deoxy-2'-epi-2'-fluorocoformycin

Details 2'-deoxy-2'-epi-2'-fluorocoformycin 2'-deoxy-2'-epi-2'-fluorocoformycin

1997-12-15

1999-03-23

Fonda, Kathleen K.

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

Organic compounds

Carbohydrates or derivatives

536 221, 536 2713, 536 288, 536 291, 549475, 549480, 549504, C07H 1916

Patent

active

058861670

ABSTRACT:
2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.

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