ISSN 1070-4272, Russian Journal of Applied Chemistry, 2006, Vol. 79, No. 2, pp. 327!328. + Pleiades Publishing, Inc., 2006.
Original Russian Text + M. K. Ibraev, A. T. Takibaeva, A. M. Gazaliev, O. A. Nurkenov, S. D. Fazylov, 2006, published in Zhurnal Prikladnoi Khimii,
2006, Vol. 79, No. 2, pp. 328!329.
Synthesis of Isonicotinic Acid Vinyloxyethylthiosemicarbazide
M. K. Ibraev, A. T. Takibaeva, A. M. Gazaliev, O. A. Nurkenov, and S. D. Fazylov
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan,
Limited Liability Company, Karaganda, Kazakhstan
Received June 7, 2005
Abstract-The reaction of isonicotinic acid hydrazide with vinyloxyethyl isothiocyanate was studied.
The reaction product exhibits antifungal activity toward Candida albicans strain.
Isonicotinic acid hydrazide I, which exhibits strong
antitubercular effect and is an antagonist of nicotin-
amide, the factor of redox processes in a cell, is un-
doubtedly of interest in a search for new physiological-
ly active substances .
Many hydrazine derivatives exhibit a broad spec-
trum of biological activity, depending on the structure,
position, and reactivity of substituents. Therefore, it is
of particular interest to prepare hydrazine derivatives
from vinyloxyethyl isothiocyanate, because introduc-
tion of a sulfur atom into organic molecules decreases
their toxicity and gives rise to new types of biological
With the aim to search for new bioactive sub-
stances and reveal structure3bioactivity relationships,
we performed the reaction of isonicotinic acid hydra-
zide I with vinyloxyethyl isothiocyanate II. The reac-
tion was performed at equimolar ratio of the reactants
in alcohol at 0+5oC with the subsequent heating to
Compound III obtained from this reaction is a
white crystalline substance soluble in organic solv-
ents. Its structure and composition were confirmed by
elemental analysis and IR spectroscopy. The IR spec-
trum of III exhibits characteristic absorption bands of
N3H, NHCS, CH
=CH, and C=S stretching vibrations
at 346033440, 151031500, 164531640, and 12203
, respectively. The bending mode of the
NH3CO3 group is manifested at 165031645 cm
Compound III was tested for the bactericidal ac-
tivity against a series of strains, and its antifungal
activity against Candida albicans strain was re-
The IR spectrum was recorded on an AVATAR-
320 device (KBr pellets).
Isonicotinic acid vinyloxyethylthiosemicarbazide
III. A solution of 2.56 g of vinyloxyethyl isothiocya-
nate II in 5 ml of ethanol was slowly added to a solu-
tion of 2.74 g of isonicotinic acid hydrazide I in 15 ml
of ethanol. After the whole amount of II was added,
the mixture was stirred while heating to 45355oC over
a period of 233 h. The solvent was distilled off, and
4.85 g (91%) of isonicotinic acid vinyloxyethylthio-
semicarbazide III was obtained; mp 1933195oC.
Found, %: C 49.62, H 5.26, N 21.05.
Calculated, %: C 49.56, H 5.22, N 21.0.
The antimicrobial activity of III was studied by
the procedure described in . The sensitivity of
microorganisms to the compound was evaluated by