was demonstrated by spectral methods and X-ray diffraction structural analysis.Keywords: 5-aryl-3-(-thiomorpholinoethyl)-1,2,4-oxadiazoles, 2-amino-8-thia-1-aza-5-azoniaspiro-[4.5]dec-1-ene chloride hydrate, substituted benzoic acids, acid hydrolysis, X-ray diffraction structural analysis.The possibility that -amino-O-aroylpropioamidoximes and 3-(-aminoethyl)-5-aryl-1,2,4-oxadiazoles exist both as stable bases and hydrochlorides has been demonstrated in our previous work, in which -piperidine, -morpholine, and -benzimidazole derivatives are described. These compounds do not undergo structural change upon isolation from the reaction mixture and recrystallization. Physicochemical and spectral data as well as X-ray diffraction structural data were obtained for these compounds [1][2][3]. Scheme 1 N NH 2 N OH N S O C 6 H 4 X NH 2 N O N O N C 6 H 4 X N XC 6 H 4 COCl N NH 2 N OH S S S -H 2 O 3 2a-e 1a-e 3·2HCl 2HCl HCl · 1,2 a X = p-MeO, b X = p-Me, c X = H, d X = p-Br, e X = m-Cl
The search for new tuberculostatics is an important task for medicinal chemistry. A series of new O-aroylb-(4-phenylpiperazin-1-yl)propioamidoximes were synthesized and tested in vitro for antituberculosis activity. The synthesis of the target substances consists of 3 -4 steps. In the first step, b-(4-phenylpiperazin-1-yl)propionitrile was obtained in 79% yield; the second step yields b-(4-phenylpiperazin-1-yl)propioamidoxime in 75% yield. Subsequent aroylation of this amidoxime by substituted benzoic acid chlorides in the presence of Et 3 N leads to the target O-aroyl-b-(4-phenylpiperazin-1-yl)propioamidoximes in 61 -93% yields. Hydrochlorides of the O-aroylated products were obtained in 72 -94% yields by the action of ethereal HCl on solutions of the bases. PMR spectra of hydrochlorides of the O-aroylated products show evidence of slow inversion of the heterocycle at the b-position and coordination of HCl at the N1 atom of the 4-phenylpiperazine fragment. Some bases and hydrochlorides of O-aroyl-b-(4-phenylpiperazin-1-yl)propioamidoximes exhibited interesting antituberculosis properties when tested in vitro on sensitive, resistant, and multi-drug resistant strains of M. tuberculosis.
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