SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF <i>N</i>-ALKYL-SUBSTITUTED 4-ARYLDIAZENYLPYRAZOLES
DOI:
https://doi.org/10.1007/519Keywords:
pyrazoles, regioisomers, alkylation, deacylation, tuberculostatic and antibacterial activityAbstract
Alkylation of 4-aryldiazenylpyrazoles using (4-bromobutyl)acetate and [(2-acetoxyethoxy)methyl]-acetate gave the corresponding 1-(4-acetoxybutyl)- and 1-[(2-acetoxyethoxy)methyl]pyrazoles. 3-Fluoroalkyl-4-aryldiazenylpyrazoles react with (4-bromobutyl)acetate to form a mixture of the regio-isomeric 1-(4-acetoxybutyl)-3- and 1-(4-acetoxybutyl)-5-fluoroalkylpyrazoles. Several of the acetoxypyrazole derivatives were deacylated and isolated using HPLC. Modest activity towards the ATCC 6633 strain of bacteria Bacillus subtilis has been found for 1-(4-hydroxybutyl)-5-methyl-4-[(4-methylphenyl)diazenyl]-3-(octafluorobutyl)-1H-pyrazole.
Authors: A. E. Ivanova, Ya. V. Burgart, and V. I. Saloutin.
English Translation in Chemistry of Heterocyclic Compounds, 2013, 49 (8), pp 1128-1135