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KMID : 0043319980210020187
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Archives of Pharmacal Research
1998 Volume.21 No. 2 p.187 ~ p.192
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Synthesis of the 7,8-Dihydro-7-deazapurine Derivatives and Their Antibiotic Activity
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Sung Sun-Young
Shin Kwan-Seog
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Abstract
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The cis- and trans-diastereomers of the 7,8-dihydro-7-deazapurine derivatives were synthesized from the corresponding diastereomers of 4-tran5-cyano-2-methyl-3-phenyl-5-oxopyrrolidine (5), which were reduced from the 2-cis- and 2-tran5-diastereomers of 4-trans-cyano-2-hydroxymethyl-3-phenyl-5-oxopyrrolidine (2) via tosylation, iodination and following elimination respectively. The prepared cis- and ttans-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.
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KEYWORD
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Deoxygenation, 4-Cyano-2-methyl-3-phenyl-5-oxopyrrolidine
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