Synthesis of the 7,8-dihydro-7-deazapurine derivatives and their antibiotic activity.
The cis- and trans-diastereomers of the 7,8-dihydro-7-deazapurine derivatives were synthesized from the corresponding diastereomers of 4-trans-cyano-2-methyl-3-phenyl-5-oxopyrrolidine (5), which were reduced from the 2-cis- and 2-trans-diastereomers of 4-trans-cyano-2-hydroxymethyl-3-phenyl-5-oxopyrrolidine (2) via tosylation, iodination and following elimination, respectively. The prepared cis- and trans-diastereomers of 6-amino-2-mercapto-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (8) were transferred to the corresponding 2-methylthio-diastereomers 9 and following desulfurization with Raney-nickel leaded to the cis- and trans-diastereomers of 6-amino-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (10), respectively. The synthesized 7-deazapurine derivatives were tested for their antibiotic activity by the serial two-fold dilution method.
Sung
S Y
SY
College of Pharmacy, Kangwon National University, Chuncheon, Korea.
Sin
K S
KS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D001419:Bacteria / Q000187:drug effects*; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D011687:Purines / Q000138:chemical synthesis* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D011687:Purines