Synthesis, structure, and antimycobacterial activity of 6-[1(3 H)-isobenzofuranylidenemethyl]purines and analogs

6-Substituted 9-benzylpurines have been synthesized and their activities against Mycobacterium tuberculosis determined. Tautomery of the compounds was studied by NMR, X-ray, and ab initio calculations. 6-Benzofuryl-, styryl, benzyl, and furfurylpurines as well as 6-[1(3 H)-isobenzofuranylidenemethyl...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2009-09, Vol.17 (18), p.6512-6516
Main Authors: Brændvang, Morten, Bakken, Vebjørn, Gundersen, Lise-Lotte
Format: Article
Language:English
Subjects:
Ab initio calculations
Animals
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antimycobacterials
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Biological and medical sciences
Cell Survival - drug effects
Cercopithecus aethiops
Cross-couplings
Crystallography, X-Ray
Medical sciences
Microbial Sensitivity Tests
Models, Molecular
Mycobacterium tuberculosis
Mycobacterium tuberculosis - drug effects
Pharmacology. Drug treatments
Purines
Purines - chemical synthesis
Purines - chemistry
Purines - pharmacology
Structure-Activity Relationship
Tuberculosis - drug therapy
Vero Cells
X-ray
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Summary:6-Substituted 9-benzylpurines have been synthesized and their activities against Mycobacterium tuberculosis determined. Tautomery of the compounds was studied by NMR, X-ray, and ab initio calculations. 6-Benzofuryl-, styryl, benzyl, and furfurylpurines as well as 6-[1(3 H)-isobenzofuranylidenemethyl]purines have been synthesized and their activities against Mycobacterium tuberculosis ( Mtb) determined. Several compounds displayed profound antimycobacterial activity in combination with low toxicity towards mammalian cells. NMR and X-ray crystallography were employed to determine the detailed structures and the results were supported by quantum chemical calculations.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2009.08.012