ISSN 1070-4272, Russian Journal of Applied Chemistry, 2008, Vol. 81, No. 4, pp. 651!656. + Pleiades Publishing, Ltd., 2008.
Original Russian Text + S.V. Kurbatova, O.V. Parshikova, Z.P. Belousova, 2008, published in Zhurnal Prikladnoi Khimii, 2008, Vol. 81, No. 4,
AND INDUSTRIAL ORGANIC CHEMISTRY
Correlation between the Structure and Chromatographic
Retention of Some Azole Derivatives
S. V. Kurbatova, O. V. Parshikova, and Z. P. Belousova
Samara State University, Samara, Russia
Received February 22, 2007
Abstract-The chromatographic retention of nitrogen-containing heterocycles was studied in relation to
their structure. The role of the type and position of the substituents and functional groups in the chro-
matographic behavior of these compounds was demonstrated. THe separation in a selected chromatographic
system was studied in relation to the dipole moment of the sorbates.
Nitrogen-containing heterocycles exhibit a wide
range of biological activity [13 4]. Many of these
compounds are widely used for preparing vasodilating
and antispasmodic (Dibasol), antimicrobial (metronid-
azole), analeptic (Etimizol), adrenomimetic (naphthi-
zin), and other pharmaceuticals. In addition, many
important natural compounds such as histamine, his-
tidine, allantoin, etc., contain an imidazole fragment.
Promising in this respect are sulfonic acid imidaz-
olides, some of which exhibit antiviral, antitubercu-
lous, antifungal, and other activities [4, 5].
An important step in preparation of biologically
active compounds is identification and quality control
of the pharmaceuticals prepared since they can be con-
taminated with intermediate products or isomers.
High-performance liquid chromatography (HPLC) is
one of powerful tools for analysis of heterocyclic
compounds. This method is also used in physico-
chemical considered . A study of the chromatog-
raphic behavior of nitrogen-containing heterocyclic
derivatives can give insight into the retention mech-
anism of other heterocyclic compounds. Based on
the results of such studies, the selectivity of chro-
matographic systems can be predicted and the con-
ditions of chromatographic separation can be opti-
Derivatives of five-membered heterocycles are
polyfunctional compounds containing several sorption
sites which can interact with the components of
the chromatographic system (sorbent and eluent).
The retention factors of the simplest imidazole deriv-
ates under the HPLC conditions, some physicochem-
ical and topological properties of these compounds,
and correlations between these parameters were
studied in [4, 5, 7]. It should be noted that, because
the range of the compounds listed was not represen-
tative, no general conclusions on how the structure of
azoles and their derivatives affects their HPLC be-
havior were made. In this study we extended the range
of azoles examined by including triazole and tetrazole
derivatives and the derivatives with hydroxy, hy-
drazide, and nitro groups.
The aim of this study was to determine the correla-
tion between the structure of some azole derivatives
and their retention under conditions of reversed-phase
HPLC (RP HPLC).
The experiments were performed on a Biotronik
Chromatographic system with a BT 8100 HPLC
Pump. A 4 0 150 mm column packed with Separon
(grain size 6 mm) was used. The elution was
performed in the isocratic mode using an acetonitrile3
water mixture (1 : 1, 5 : 3, and 3 : 1, v/v) as the el-
Prior to analysis, the eluent was degassed with
a UZDN-2T degasser and filtered. Substrate solutions
were prepared by dissolution of dry pure heterocyclic
compounds in appropriate solvents. The volume of
an injected sample was 20 ml. Sodium nitrite was used
as nonsorbed compound. The structural formulas and
names of the compounds are listed in Table 1.
The compounds were prepared at the Chair of Organic
Chemistry of Samara State University.