Synthesis of the 7,8-dihydro-7-deazapurine derivatives and their antibiotic activity

Thecis- andtrans-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-oxopyrro...

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Bibliographic Details
Published in:Archives of pharmacal research 1998-04, Vol.21 (2), p.187-192
Main Authors: Sung, Sun Young, Sin, Kwan Seog
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
antibacterial properties
antibiotics
Bacillus subtilis - drug effects
Bacteria - drug effects
diastereomers
Escherichia coli - drug effects
iodination
Microbial Sensitivity Tests
nickel
Purines - chemical synthesis
Purines - pharmacology
Staphylococcus aureus - drug effects
Structure-Activity Relationship
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Summary:Thecis- andtrans-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 preparedcis- andtrans-diastereomers of 6-amino-2-mercapto-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (8) were transferred to the corresponding 2-methylthio-diastereomers9 and following desulfurization with Raney-nickel leaded to thecis-andtrans-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.
ISSN:0253-6269
1976-3786
DOI:10.1007/BF02974026