ChemInform Abstract: Novel Synthesis of Caffeine Iodomethylate and Its Homologue.

Иванов, Э. И.; Kalayanov, G. D.; Yaroshchenko, I. M.; Stepanov, D. E.

doi:10.1002/chin.199024189

Cited by 1 publication

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“…Methylated caffeine, 1,3,7,9-tetramethylxanthinium iodide, 1 , was synthesized by refluxing caffeine with an excess of methyl iodide in DMF using a modified literature procedure (Scheme ) 10b. Compound 1 is a water-soluble solid and stable in air up to its melting point.…”

Section: Resultsmentioning

confidence: 99%

“…The first step in the synthesis of an NHC silver complex from caffeine is to obtain an imidazolium salt precursor, such as 1,3,7,9-tetramethylxanthinium, also known as methylated caffeine 1 . Previously, our group has reported the synthesis of methylated caffeine with various counterions, and the formation of its biscarbene silver complexes by in situ deprotonation with silver oxide .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis from Caffeine of a Mixed N-Heterocyclic Carbene−Silver Acetate Complex Active against Resistant Respiratory Pathogens

et al. 2006

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The bis(N-heterocyclic carbene) (NHC) silver complex, 3, with a methyl carbonate anion was formed from the reaction of the iodide salt of methylated caffeine, 1, with silver (I) oxide in methanol. Attempts to crystallize this complex from a mixture of common alcohols and ethyl acetate led to the formation of an NHC-silver acetate complex, 4. The more direct synthesis of 4 was accomplished by the in-situ deprotonation of 1 by silver acetate in methanol. Complex 4 demonstrated antimicrobial activity against numerous resistant respiratory pathogens from the lungs of cystic fibrosis (CF) patients including members of the Burkholderia cepacia complex that cause a high rate of mortality in patients with cystic fibrosis (CF). Application of this NHC silver complex to primary cultures of murine respiratory epithelial cells followed by microarray analysis showed minimal gene expression changes at the concentrations effective against respiratory pathogens. Furthermore, methylated caffeine without silver showed some antibacterial and antifungal activity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%