Synthesis and tuberculostatic activity of some (4-phenylpiperazin-1-ylmethyl)-1,3,4-oxadiazole and (4-phenylpiperazin-1-ylmethyl)-1,2,4-triazole derivatives.
The phenylpiperazineacetic hydrazide cyclization product. 5-(4-phenylpiperazin-1-ylmethyl)-1,3,4-oxadiazole-2-thiol (1) upon alkylation gave the S-methyl derivative (2). next it was tranmsformed into 1-phenyl-4-(5-pyrrolidin-1-yl-1,3,4-oxadiazol-2-ylmethyl)-piperazine (3). Upon the reaction of I with 1.2-dibromoethane. the derivative (4) containing two joint 1,3,4-oxadiazole systems was obtained. The reactions of compound 1 with chloroacetonitrile and chloroacetic acid gave the corresponding nitrile and carboxylic acid (5, 6) as well. The 4-amino-1,2,4-triazole-3-thiol derivative (7) was obtained in the reaction of compound I with hydrazine hydrate. The phenylpiperazinacetic acid hydrazide was transformed into 1,3,4-oxadiazol-2-ylamine (8), and this, subsequently, into the 2-ethoxy-1,2,4-triazole derivative (9). The compounds obtained were tested in vitro for their tuberculostatic activity. The minimum inhibiting concentrations (MIC) were within 25 - 100 mg/ml.
Foks
Henryk
H
Department of Organic Chemistry, Medical University of Gdańsk, 80-416 Gdańsk, Poland. hfoks@amg.gda.pl
Pancechowska-Ksepko
Danuta
D
Janowiec
Mieczysław
M
Zwolska
Zofia
Z
Augustynowicz-Kopeć
Ewa
E
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology*; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
C500124:(4-phenylpiperazin-1-ylmethyl)-1,2,4-triazole; C500123:(4-phenylpiperazin-1-ylmethyl)-1,3,4-oxadiazole; D000995:Antitubercular Agents; D007202:Indicators and Reagents; D010069:Oxadiazoles; D010879:Piperazines; D010880:Piperidines; D014230:Triazoles