Articles
Glucose ester derivatives of aminosalicylic acids*

https://doi.org/10.1002/jps.3030440804Get rights and content

Abstract

Glucose esters of 4‐ and 5‐aminosalicylic acid were obtainable by reaction of the benzyloxynitrobenzoic acid chlorides with diacetone glucose, followed by catalytic hydrogenation of the nitro groups. Conversion of the amines to hydrochlorides removed one or both of the acetone groups from the glucose. Complete removal of the acetone groups gave a glucose ester that was unstable on standing, but the protected glucose esters were found to be stable. The free‐amino ester of 4‐amino‐salicylic acid was obtained in excellent yield for tuberculostatic and toxicity determinations.

References (16)

  • R. Williams

    Biochem.

    (1940)
    A. Di Somma

    J. Biol. Chem.

    (1940)
    W. Goebel

    J. Biol. Chem.

    (1937)
  • E. Grunberg et al.

    Yale J. Biol. and Med.

    (1952)
    H. Fox

    J. Org. Chem.

    (1953)
    P. Sah

    J. Am. Chem. Soc.

    (1953)
    H. Yale

    J. Am. Chem. Soc.

    (1953)
    J. Bernstein

    Am. Rev. Tuberc.

    (1953)
  • C. Sannié et al.

    Bull. soc. chim. France

    (1950)
  • W. Barclay

    Am. Rev. Tuberc.

    (1949)
    W. Boger et al.

    Am. Rev. Tuberc.

    (1950)
  • W. Foye et al.

    THIS JOURNAL

    (1953)
  • E. Way et al.

    THIS JOURNAL

    (1955)
  • G. Haberland

    Arzneimittel‐Forsch.

    (1951)
  • J. Lehmann

    Nord. Med.

    (1947)
There are more references available in the full text version of this article.

Cited by (0)

*

Wisconsin Alumni Research Foundation Fellow, 1952‐1953; Fellow of the American Foundation for Pharmaceutical Education, 1953‐1955.

View full text