Synthesis of anthraquinonyl glucosaminosides and studies on the influence of aglycone hydroxyl substitution on superoxide generation, DNA binding, and …

HN Abramson, JW Banning, JP Nachtman…

Index: Abramson; Banning; Nachtman; Roginski; Sardessai; Wormser; Wu; Nagia; Schroeder; Bernardo Journal of Medicinal Chemistry, 1986 , vol. 29, # 9 p. 1709 - 1714

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Citation Number: 15

Abstract

A series of anthraquinonyl glucosaminosides (10a-e) were synthesized by Koenigs-Knorr glycosidation of the corresponding aglycones (1 la-e) with bromo sugar 12 followed by saponification. These glycosides were intended to serve as models to study the role played by the hydroxyl substituents on the aglycone portion of the antitumor anthracycline antibiotics. Superoxide generation as measured in rat heart sarcosomes was found to ...

 Related Synthetic Route
N/A Structure

102830-97-7

N/A

~52%

3-[[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,8-dihydroxyanthracene-9,10-dione Structure

102831-03-8

3-[[(2R,3R,4R,5...

3,4,6-tri-O-acetyl-2-deoxy-2-N--trifluoroacetamido--α-D-glucopyranosyl bromide Structure

6736-63-6

3,4,6-tri-O-ace...

~%

3-[[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,8-dihydroxyanthracene-9,10-dione Structure

102831-03-8

3-[[(2R,3R,4R,5...

Aloeemodin Structure

481-72-1

Aloeemodin

~%

3-[[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,8-dihydroxyanthracene-9,10-dione Structure

102831-03-8

3-[[(2R,3R,4R,5...

1,4-dihydroxy-2-((3,4,6-tri-O-acetyl-2-deoxy-2-((trifluoroacetyl)amino)-β-D-glucosyloxy)methyl)-9,10-dihydro-9,10-anthracenedione Structure

102830-95-5

1,4-dihydroxy-2...

~62%

2-[[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,4-dihydroxyanthracene-9,10-dione Structure

102831-01-6

2-[[(2R,3R,4R,5...

3,4,6-tri-O-acetyl-2-deoxy-2-N--trifluoroacetamido--α-D-glucopyranosyl bromide Structure

6736-63-6

3,4,6-tri-O-ace...

~%

2-[[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,4-dihydroxyanthracene-9,10-dione Structure

102831-01-6

2-[[(2R,3R,4R,5...

1,4-Dihydroxy-2-(hydroxymethyl)-9,10-anthraquinone Structure

22296-59-9

1,4-Dihydroxy-2...

~%

2-[[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-1,4-dihydroxyanthracene-9,10-dione Structure

102831-01-6

2-[[(2R,3R,4R,5...


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