Back to Search
Start Over
Synthesis of anthraquinonyl glucosaminosides and studies on the influence of aglycone hydroxyl substitution on superoxide generation, DNA binding, and antimicrobial properties
- Source :
- Journal of Medicinal Chemistry. 29:1709-1714
- Publication Year :
- 1986
- Publisher :
- American Chemical Society (ACS), 1986.
-
Abstract
- A series of anthraquinonyl glucosaminosides (10a-e) were synthesized by Koenigs-Knorr glycosidation of the corresponding aglycones (11a-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 increase with the addition of successive hydroxyl groups to the anthraquinone nucleus. The 1,8-dihydroxy pattern was determined to generate significantly less superoxide than the 1,4-dihydroxy pattern. Hydroxyl substitution was also observed to stabilize the complex formed between the anthraquinones and DNA and was required for antibacterial activity against a number of Gram-positive organisms.
- Subjects :
- Male
Chemical Phenomena
Stereochemistry
Anthraquinones
Gram-Positive Bacteria
Anthraquinone
Structure-Activity Relationship
chemistry.chemical_compound
Glucosides
Superoxides
Drug Discovery
Animals
Glycosides
Antibacterial agent
chemistry.chemical_classification
Glucosamine
Superoxide
Myocardium
Glycoside
Heart
Rats, Inbred Strains
DNA
Rats
Quinone
Chemistry
Aglycone
chemistry
Molecular Medicine
Cattle
Antibacterial activity
Subjects
Details
- ISSN :
- 15204804 and 00222623
- Volume :
- 29
- Database :
- OpenAIRE
- Journal :
- Journal of Medicinal Chemistry
- Accession number :
- edsair.doi.dedup.....2a4c0239e8294a444d3b91d504c3e6a6