Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 5, pp. 928−930.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
V.M. Farzaliev, M.T. Abbasova, A.A. Ashurova, G.B. Babaeva, N.P. Ladokhina, Ya.M. Kerimova, 2009, published in Zhurnal Prikladnoi
Khimii, 2009, Vol. 82, No. 5, pp. 871−873.
Synthesis of N,N'-Bis(alkyloxymethyl)piperazines
and Examination of Their Antimicrobial Properties
V. M. Farzaliev, M. T. Abbasova, A. A. Ashurova, G. B. Babaeva,
N. P. Ladokhina, and Ya. M. Kerimova
Kuliev Institute of Chemistry of Additives, National Academy of Sciences Azerbaijan, Baku, Azerbaijana
Received April 23, 2008
Abstract—Three-component condensation of piperazine with formaldehyde and aliphatic alcohols was employed
for elucidating the possibility to synthesize N,N '-bis(alkyloxymethyl)piperazines. The structure of the resulting
compounds was identified by 1H NMR spectroscopy. The antimicrobial properties of these compounds were
examined with respect to microorganisms that infect cooling lubricants and lubricant oils.
A promising line in modern petrochemistry and micro-
biology is synthesis of bacteria-resistant compounds
whose action is underlain by the “in statu nascendi”
principle. Meant by these agents are those having the
basic active substance in a certain “depot” (in the bound
state) which gradually releases the active toxophore part
which exhibits prolonged action.
Today, extensive application as such “depots” is found
by compounds containing “bound” formaldehyde [1,
2]. Some researchers  believe that these agents owe
their antimicrobial action to the capability for hydrolytic
decomposition with formation of formaldehyde. In turn,
formaldehyde which possesses alkylating property can
irreversibly react with various nucleophilic centers of the
substrate (hydroxy, sulfohydryl, and carboxy, as well as
amino groups). This blocks one of the cell cycle phases,
thereby suppressing the growth of microorganisms.
At the same time, the antimicrobial activity of these
compounds can be associated not only with direct toxic
action of the active part of the molecule on cells, but also
with the nature of the carrier of the toxophore group.
This may offer prospects of directed variation of the
antimicrobial properties via using organic radicals of
different nature as carrier of the toxophore group.
Earlier [4, 5] we employed three-component con-
densation–heterocyclization of alkanolamines (or alkyl-
enediamines) with formaldehyde and hydroxy-containing
compounds for synthesizing alkyloxy-methyl derivatives
of 1,3-diheterocycloalkanes (1,3-oxaza- and 1,3-diaza-
cycloalkanes) containing bound formaldehyde.
The results of those tests, along with a high antimicrobial
activity of these compounds, suggest that this activity
varies with the nature of the toxophore group carrier:
the nature of the heterocycle (heterocycles containing
diaza group perform better than do those containing
oxaza group, and 6-membered heterocycles, better than
do 5-membered heterocycles) and the length of the alkyl
radical in the alkyloxymethyl group.
To continue those studies, we carried out here
condensation of piperazine with formaldehyde and
aliphatic alcohols into N,N'-bis(alkyloxymethyl)pipera
where R = (a) –CH
; (b) –C
; (c) –C
; (d) iso-
; (e) n–C
; (f) iso-C
; (g) n-C
; and (h)