Russian Journal of Applied Chemistry, 2009, Vol. 82, No. 10, pp. 1832−1834.
Pleiades Publishing, Ltd., 2009.
Original Russian Text
A.N. Gafarov, A.I. Nugmanov, 2009, published in Zhurnal Prikladnoi Khimii, 2009, Vol. 82, No. 10, pp. 1680−1682.
STUDIES IN THE FIELD OF CHEMISTRY OF NITRO COMPOUNDS
(TO 100TH BIRTHDAY ANNIVERSARY OF S. S. NOVIKOV)
of 2-Substituted 5-Nitrofuran Derivatives
A. N. Gafarov and A. I. Nugmanov
Kazan State Technological University, Kazan, Tatarstan, Russia
Received July 21, 2009
Abstract—Quantum-chemical parameters of molecules of 2-substituted 5-nitrofuran derivatives were calculated
using the GAMESS software package and their correlation with the antibacterial activity of the compounds was
analyzed. Regression analysis technique was employed to find linear relationships between the logarithm of the
average inhibiting concentration of 5-nitrofuran derivatives and the quantum-chemical parameters. The largest
correlation coefficient (0.932) was found for the dependence of the antibacterial activity on the amount of charge
on the nitrogen atom of the nitro group. The results obtained are in agreement with modern concepts about the
nature of the antibacterial activity of 2-substituted 5-nitrofuran derivatives.
The comparatively fast habituation of microorganisms
to chemotherapeutic preparations stimulates a permanent
search for new effective antibacterial means. The still
used total screening practice requires a large expenditure
of resources and loss of time and is characterized by a low
probability of success. For prognosticating new effective
medicinal preparations, it seems promising to reveal a
relationship between the structure and biological activity
in local series of biologically active compounds having
the common basic chemical structure. In this context,
particular attention is being given to analysis of 5-nitro-
furan derivatives containing substituents in position 2 of
the heteroring. Some derivatives of this series possess
a broad spectrum of antibacterial activity and are effective
against antibiotic-resistant infectious agents.
As a rule, 5-nitrofuran derivatives containing
substituents in position 3 have no antibacterial properties.
It has also been noted that the antibacterial activity of
5-nitrofuran derivatives grows as the electron-acceptor
capacity of a substituent in position 2 increases [2, 3].
A rough correlation has been revealed between
the antibacterial activity of 2-substituted 5-nitrofuran
derivatives and the potential of polarographic reduction
of the nitro group and the energy of the lowest unoccupied
orbital, calculated by the LCAO-MO method .
To find a more precise correlation between the
antibacterial activity of 5-nitrofuran derivatives containing
a substituent in position 2 and the electronic structure,
we analyzed the relationship between the antibacterial
activity, on the one hand, and the HOMO and LUMO
energies, partial charges on atoms of the furan ring,
hydrophilic–lipophilic balance, and interatomic distances
calculated using the GAMESS software package, on the
We used the following numbering of atoms in 5-nitro-
The following parameters were calculated for
5-nitrofuran derivatives: Q1, Q2, Q3, Q4, Q5, Q6, Q7,
Q8, Q9, and Q10 are the partial charges on atoms 1, 2, 3,
4, 5, 6, 7, 8, 9, and 10, respectively; R 5–6, R 7–8, and R
7–9, interatomic distances between atoms 5 and 6, 6 and
7, and 7 and 9, respectively; log P, hydrophilic–lipophilic