Synthesis, biological activity, and SAR of antimycobacterial 9-aryl-, 9-arylsulfonyl-, and 9-benzyl-6-(2-furyl)purines.

doi:10.1021/JM0408924

Paper

Synthesis, biological activity, and SAR of antimycobacterial 9-aryl-, 9-arylsulfonyl-, and 9-benzyl-6-(2-furyl)purines.

Published Mar 1, 2005 · A. K. Bakkestuen, L. Gundersen, B. T. Utenova

Journal of medicinal chemistry

Q1 SJR score

105

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1

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Abstract

9-Aryl-, 9-arylsulfonyl- and 9-benzyl-6-(2-furyl)purines were synthesized by N-alkylation or N-arylation of the purine followed by Stille coupling to introduce the furyl substituent in the 6-position and the compounds screened for activity against Mycobacterium tuberculosis. The 9-aryl- and 9-sulfonylarylpurines exhibited weak activity toward the bacteria, but 9-benzylpurines were good inhibitors especially those carrying electron-donating substituents on the phenyl ring. A chlorine atom in the purine 2-position further enhanced activity. The high antimycobacterial activity (MIC 0.39 microg/mL against M. tuberculosis), low toxicity against mammalian cells and activity inside macrophages found for 2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine makes this compound a highly interesting potential antituberculosis drug.

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Study Snapshot

2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)-9H-purine shows high antimycobacterial activity, low toxicity to mammals, and activity inside macrophages, making it a promising potential antituberculosis drug.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis, biological activity, and SAR of antimycobacterial 9-aryl-, 9-arylsulfonyl-, and 9-benzyl-6-(2-furyl)purines.

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References

Citations

Functionalization of Fe3O4@SiO2 nanoparticles with Cu(i)-thiosemicarbazone complex as a robust and efficient heterogeneous nanocatalyst for N-arylation of N-heterocycles with aryl halides

Fe3O4@SiO2-[CuL] is a robust, efficient, and eco-friendly nanocatalyst for N-arylation of N-heterocycles with aryl halides, enabling multiple reusability without significant performance decline.

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