Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів
A number of 1,3-thiazol-2-yl hydrazones of aromatic aldehydes were synthesized and tested for antifungal activity. It was found two promising compounds: 2-[(1Z)-[2-(4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl]pyridine has MIC of 8 μg/ml against Cryptococcus neoformans and MIC of 16 μg/ml aga...
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V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
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| author | Tarnavskiy, Sergiy S. Lukashov, Sergiy S. Bdzhola, Volodymyr G. Voitiuk, Volodymyr V. Yarmoluk, Sergiy M. |
| author_facet | Tarnavskiy, Sergiy S. Lukashov, Sergiy S. Bdzhola, Volodymyr G. Voitiuk, Volodymyr V. Yarmoluk, Sergiy M. |
| author_institution_txt_mv | [
{
"author": "Sergiy S. Tarnavskiy",
"institution": "Institute of Molecular Biology and Genetics of the NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Sergiy S. Lukashov",
"institution": "Institute of Molecular Biology and Genetics of the NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Volodymyr G. Bdzhola",
"institution": "Institute of Molecular Biology and Genetics of the NAS of Ukraine, Kyiv, Ukraine "
},
{
"author": "Volodymyr V. Voitiuk",
"institution": "Scientific Service Company «OTAVA», LLC, Kyiv, Ukraine"
},
{
"author": "Sergiy M. Yarmoluk",
"institution": "Institute of Molecular Biology and Genetics of the NAS of Ukraine, Kyiv, Ukraine"
}
] |
| author_sort | Tarnavskiy, Sergiy S. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-19T14:56:55Z |
| description | A number of 1,3-thiazol-2-yl hydrazones of aromatic aldehydes were synthesized and tested for antifungal activity. It was found two promising compounds: 2-[(1Z)-[2-(4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl]pyridine has MIC of 8 μg/ml against Cryptococcus neoformans and MIC of 16 μg/ml against Candida albicans and 4-[(1Z)-{2-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazin-1-ylidene}methyl]-2,6-dimethoxy-phenol has MIC of 0.5 μg/ml against Cryptococcus neoformans, respectively |
| doi_str_mv | 10.15407/bioorganica2024.02.037 |
| first_indexed | 2025-07-17T12:20:05Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2024, Vol. 19, N 2
UDC 547.388.3 + 547.789.1
DOI: https://doi.org/10.15407/bioorganica2024.02.037
37
SHORT COMMUNICATION
Synthesis and study of antifungal activity of aromatic aldehyde
1,3-thiazol-2-yl hydrazones
Sergiy S. Tarnavskiy1, Sergiy S. Lukashov1, Volodymyr G. Bdzhola1, Volodymyr V. Voitiuk2,
Sergiy M. Yarmoluk1
1 Institute of Molecular Biology and Genetics of the NAS of Ukraine, Kyiv, Ukraine
2 Scientific Service Company «OTAVA», LLC, Kyiv, Ukraine
Abstract: A number of 1,3-thiazol-2-yl hydrazones of aromatic aldehydes were synthesized and tested for antifungal activity. It was found
two promising compounds: 2-[(1Z)-[2-(4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl]pyridine has MIC of 8 μg/ml against
Cryptococcus neoformans and MIC of 16 μg/ml against Candida albicans and 4-[(1Z)-{2-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-
yl]hydrazin-1-ylidene}methyl]-2,6-dimethoxy-phenol has MIC of 0.5 μg/ml against Cryptococcus neoformans, respectively.
Keywords: 1,3-thiazol-2-yl hydrazone; antifungal activity; Cryptococcus neoformans; Candida albicans.
Introduction
One of the current challenges in the treatment of many
diseases is the mutation of microorganisms. With the rapid
global spread of “superbugs” the situation with drug-
resistant pathogens has become threatening. The World
Health Organization (WHO) has recognized antimicrobal
resistance (AMR) as one of the top global public health and
development threats [1]. According to research published in
January 2022, there were an estimated 4.95 million deaths
associated with bacterial antimicrobal resistance AMR in
2019, including 1.27 million deaths attributable to bacterial
AMR and estimated number of deaths from AMR could
reach as many as 10 million annually by 2050 [2]. Given
the dynamics of the emergence of resistance in various
bacteria and fungi to known antibiotics and antifungals,
there is a continuous demand to find new antimicrobial
agents [3, 4, 5].
Received:
Revised:
Accepted:
Published online:
02.10.2024
31.10.2024
29.11.2024
30.12.2024
Corresponding author. Tel.: +380-44-200-0356;
e-mail: starn999@gmail.com (S.S. Tarnavskiy)
ORCID: 0000-0001-9656-0405
Results and Discussion
During the era of antibiotics, more than 900
antimicrobial agents were discovered, of which only about
30 are widely used in medical practice. Year by year
existing antibiotics are losing their efficacy because from
the beginning of the use encounter an irreversible biological
phenomenon – the resistance of microorganisms [6, 7, 8, 9,
10]. So scientists have an ongoing task to find ways of
overcoming this problem, in particular through the search
for new chemical compounds with antimicrobial activity.
1,3-thiazol-2-yl hydrazones of aromatic aldehydes look
promising in this regard – compounds of such a class are
known to show a variety of antiproliferative [11],
antimicrobial [12], antituberculosis [13], antifungal activity
[14, 15].
We have synthesized 145 new aromatic aldehyde
hydrazones of 1,3-thiazole bearing diverse substituents on
the 4- and 5-positions of thiazole ring. All the synthesized
compounds were tested under the antimicrobial screening
program [16] (The Community for Open Antimicrobial
Drug Discovery, CO-ADD).
Most of the 145 tested compounds did not show notable
result on antimicrobial and antifungal activity. However,
three compounds of this class have very promising MIC
values against fungal strains Cryptococcus neoformans,
© Tarnavskiy S.S. et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted
use, distribution, and reproduction in any medium, provided the original author and source are credited.
Ukrainica Bioorganica Acta
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ISSN 1814-9758. Ukr. Bioorg. Acta, 2024, Vol. 19, N 2
38
Table 1. Antimicrobial activity (MIC), cytotoxicity (CC50) and hemolytic activity (HC10) of 1,3-thiazol-2-yl hydrazone derivatives.
N
S N
H
R2
N
R1
Number R1 R2 MIC, µg/mL CC50, µg/mL HC10, µg/mL
Cn Ca Hek RBC
1 3-Br, 4-OH, 5-MeOPh 2,4-diClPh na na n.d. n.d.
2 4-OH, 3,5-DiMeOPh 2,4-diClPh 0.5 >32 >32 >32
3 3-NO2, 4-OHPh 2,4-diClPh na na n.d. n.d.
4 3-Br, 4-OH, 5-MeOPh Me >32 >32 >32 >32
5 2-Py Me 8 16 9 >32
6 3-Py Me na na n.d. n.d.
7 4-Br H >32 >32 25 >32
8 4-F H na na n.d. n.d.
AMB 1.56 1.56
FLU 8 0.125
tamoxifen 9
melittin 2.7
Cn - Cryptococcus neoformans H99 ATCC 208821; Ca - Candida albicans ATCC 90028; Hek – HEK293, human embryonic kidney cells ATCC CRL-
1573; RBC – human red blood cells; na – not active in primary screening; n.d. – not determined; AMB - amphotericin B; FLU - fluconazole.
S
N
N
H
N
R2
R1
N
N
HS
H2N
R1
NH2
N
HS
H2N O
Cl
R2
O R1
Scheme 1. А general scheme of synthesis of 1,3-thiazol-2-yl hydrazone derivatives.
Candida albicans and low cytotoxicity. For comparison, we
selected only eight compounds, which are presented for
discussion in this article.
For the synthesis of 1,3-thiazol-2-yl hydrazones
derivatives, we used known synthetic scheme based on the
reaction of aromatic aldehyde thiosemicarbazones with
chloroacetaldehyde or α-chloroketones (Scheme 1) using
sodium bicarbonate as a neutralizing agent for hydrogen
chloride. Here we are representing one-pot synthetic
procedure that not require isolation of the aldehyde
thiosemicarbazone intermediate. Simplifying the work up, it
meanwhile requires additional purification of the final
product by recrystallization from isopropanol and hot
filtration of the precipitate.
Evaluation of biological activity was carried out using
the primary screening against yeast-like fungi. The obtained
data are shown in Table 1.
Among the 1,3-thiazol-2-yl hydrazone series the most
active compounds against yeast-like fungi are 2 and 5 with
a minimum inhibitory concentration (MIC) in a range
0.5-16 μg/ml – close to the reference drugs. As it was found
(Table 1), the growth and reproduction of C. albicans
is inhibited only by compound 5 with the observed MIC –
16 μg/ml, which also is active against C. neoformans with a
MIC – 8 μg/ml. Another active compound 2 shows stronger
antifungal activity against C. neoformans with the MIC –
0.5 μg/ml, which outperforms the action of the reference
drug – fluconazole.
Among the studied substances, compound 2 deserves
special attention, because in addition to its pronounced
inhibitory activity against C. neoformans shows no
cytotoxic and hemolytic effect, which may indicate its
insignificant side effect on the macroorganism.
Conclusions
The initial screening of the newly synthesized
compounds to eveluate their antifungal and toxic properties
revealed several aromatic aldehyde 1,3-thiazol-2-yl
hydrazone derivatives with prominent antifungal activity.
Among the studied 1,3-thiazol-2-yl hydrazones, two
S.S. Tarnavskiy et al.
39
substances are noteworthy, namely compound 5 with
pronounced anticandidiasis and anti-cryptococcal activity
and compound 2 with monovalent action against C.
Neoforman.
Notes
Acknowledgments and finances.
This work was supported by the grants from the National
Academy of Sciences of Ukraine (0117U003914,
0122U201823). The antimicrobial screening performed by
CO-ADD (The Community for Antimicrobial Drug
Discovery) was funded by the Wellcome Trust (UK) and
The University of Queensland (Australia).
The authors declare no conflict of interest.
Author contributions. Author 1: synthesis of
compounds, investigation, writing most of the manuscript,
formal analysis, writing experimental section, editing.
Author 2: investigation, formal analysis, writing, review &
editing. Author 3: conceptualization, writing, editing.
Author 4: formal analysis, melting point analysis, editing.
Author 5: conceptualization, supervision.
Experimental section
All reagents were purchased from Merck company. The
structure of the synthesized substances was confirmed using
1H-NMR spectra recorded in DMSO-d6 on a “Varian
MercuryVRX-400” instrument with an operating frequency
of 400 MHz and an internal standard – TMS.
Synthesis
General procedure of synthesis 1,3-thiazol-2-hydrazin-1-
yliden derivatives:
The corresponding 10 mmol aromatic aldehyde was
added to a warm solution of 10 mmol thiosemicarbazide in
80 ml of isopropanol and refluxed for 2-10 minutes
until a fluffy precipitate formed. Then 10 mmol
2,4-dichlorophenacyl chloride (for 1, 2, 3) or chloroacetone
(for 4, 5, 6) or 40% aqueous solution of chloroacetaldehyde
(for 7, 8) were added, respectively. After refluxing for 30
minutes – 30 mmol of sodium bicarbonate was added to the
reaction mixture under stirring and reactuin mixture was
refluxed for another 30 minutes. The still warm precipitate
was filtered and washed twice with 20 ml of water and
twice with 20 ml of isopropanol. Then the precipitate was
refluxed in another 50 ml of isopropanol for 10 minutes. In
the case of complete dissolution – the solution was at first
cooled to cause precipitation. The final product was filtered
and dried.
2-Bromo-4-[(1Z)-{2-[4-(2,4-dichlorophenyl)-1,3-thiazol-
2-yl]hydrazin-1-ylidene}methyl]-6-methoxyphenol (1).
Yeild 76% as creamy crystals; mp 177 ºC. 1H NMR (400
MHz, DMSO-d6) δ 12.12 (s, 1H), 9.90 (s, 1H), 7.93 (s, 1H),
7.91 (s, 1H), 7.67 (s, 1H), 7.50 (d, J = 7.8 Hz, 1H), 7.39 (d,
J = 7.8 Hz, 1H), 7.37 (s, 1H), 7.26 (s, 1H), 3.90 (s, 3H).
4-[(1Z)-{2-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]hyd-
razin-1-ylidene}methyl]-2,6-dimethoxyphenol (2).
Yeild 73% as rosy crystals; mp 139 ºC. 1H NMR (400
MHz, DMSO-d6) δ 12.10 (s, 1H), 9.80 (s, 1H), 7.97 (s, 1H),
7.90 (d, J = 7.8 Hz, 1H), 7.71 (s, 1H), 7.53 (d, J = 7.8 Hz,
1H), 7.38 (s, 1H), 6.96 (s, 2H), 3.82 (s, 6H).
4-[(1Z)-{2-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]hyd-
razin-1-ylidene}methyl]-2-nitrophenol (3).
Yeild 71% as brown crystals; mp 240 ºC. 1H NMR (400
MHz, DMSO-d6) δ 12.11 (s, 1H), 9.80 (s, 1H), 8.34 (s, 1H),
7.97 (s, 1H), 7.91 (d, J = 7.8 Hz, 1H), 7.84 (d, J = 7.8 Hz,
1H), 7.49 (s, 1H), 7.39 (d, J = 7.8 Hz, 1H), 7.28 (s, 1H),
7.18 (d, J = 7.8 Hz 1H).
2-bromo-6-methoxy-4-[(1Z)-[2-(4-methyl-1,3-thiazol-2-
yl)-hydrazin-1-ylidene]methyl]phenol (4).
Yeild 71% as grey crystals; mp 153 ºC. 1H NMR (400
MHz, DMSO-d6) δ 12.02 (s, 1H), 9.80 (s, 1H), 7.99 (s, 1H),
7.44 (s, 1H), 7.29 (s, 1H), 6.46 (s, 1H), 3.90 (s, 3H), 2.21 (s,
3H).
2-[(1Z)-[2-(4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylide-
ne]-methyl]pyridine (5).
Yeild 76% as brown crystals; mp 198 ºC. 1H NMR (400
MHz, DMSO-d6) δ 12.02 (s, 1H), 8.52 (d, J = 4.6 Hz, 1H),
7.98 (s, 1H), 7.89 (d, J = 7.4 Hz, 1H), 7.78 (t, J = 7.5 Hz,
1H), 7.26 (t, J = 7.5 Hz, 1H), 6.39 (s, 1H), 2.21 (s, 3H).
3-[(1Z)-[2-(4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylide-
ne]-methyl]pyridine (6).
Yeild 72% as light brown crystals; mp 196 ºC. 1H NMR
(400 MHz, DMSO-d6) δ 11.94 (s, 1H), 8.79 (s, 1H), 8.53 (d,
J = 4.9 Hz, 1H), 8.18 (s, 1H), 8.05 (d, J = 7.4 Hz, 1H), 7.45
(t, J = 7.5 Hz, 1H), 6.39 (s, 1H), 2.18 (s, 3H).
2-[(Z)-2-[(4-bromophenyl)methylidene]hydrazin-1-yl]-
1,3-thiazole (7).
Yeild 73% as brown crystals; mp 193 ºC. 1H NMR (400
MHz, DMSO-d6) δ 11.92 (s, 1H), 8.01 (s, 1H), 7.62-7.58
(m, 4H), 7.22 (d, J = 7.6 Hz, 1H), 6.84 (d, J = 7.6 Hz, 1H).
2-[(Z)-2-[(4-fluorophenyl)methylidene]hydrazin-1-yl]-
1,3-thiazole (8).
Yeild 71% as light brown crystals; mp 163 ºC. 1H NMR
(400 MHz, DMSO-d6) δ 11.92 (s, 1H), 8.02 (s, 1H), 7.70 (t,
J = 7.6 Hz, 1H), 7.28-7.25 (m 3H), 6.85 (d, J = 7.6 Hz, 1H).
Activity studies
Compound preparation
To determine the minimum inhibitory concentration
(MIC) against fungi, cytotoxicity (CC50) on mammalian
ISSN 1814-9758. Ukr. Bioorg. Acta, 2024, Vol. 19, N 2
40
cells and hemolytic activity (HC10) on human erythrocytes –
solutions of compounds were prepared by sequential two-
fold dilution (1:2) from 32 to 0.25 μg/ml (or from 20 to
0.156 μM).
Antimicrobial assays
Determination of antifungal activity of the newly
synthesized compounds was carried out according to the
standard protocols of the Community for Open
Antimicrobial Drug Discovery laboratory at The University
of Queensland (Australia) with the determination of the
minimum inhibitory concentration (MIC) at which
complete/partial inhibition of growth and reproduction of
fungi is observed. The experiments used reference test
strains of yeast-like fungi (Candida albicans ATCC 90028,
Cryptococcus neoformans ATCC 208821). The work was
performed using 384-well non-binding polystyrene plates
(Fisher Scientific). Such antimicrobial agents as
amphotericin B and fluconazole served as references.
Cytotoxicity and Hemolysis assay was carried out using
HEK293 (human embryonic kidney) cells ATCC CRL-
1573 for cytotoxicity and human blood (obtained from the
Australian Red Cross Blood Service) for hemolysis assays
following the standard procedures.
References
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bacterial antimicrobial resistance in 2019: a systematic analysis. The
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3. Xiao, Y.; Yuan, P.; Sun, Y.; Xu, Y.; Deng, X.; Wang, X. et al.
Comparison of topical antifungal agents for oral candidiasis
treatment: a systematic review and meta-analysis. Oral Surg, Oral
Med, Oral Path and Oral Radiol 2022, 133, 282-291.
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activity of minocycline and azoles against fluconazole-resistant
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resistance in Candida opportunistic pathogens. Genes 2018, 9, 461-
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Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів
ароматичних альдегідів
C.C Тарнавський1*, С.С. Лукашов1, В.Г. Бджола1, В.В. Войтюк2, С.М. Ярмолюк1
1 Інститут молекулярної біології і генетики НАН України, Київ, Україна
2 ТОВ «Науково-сервісна фірма «ОТАВА», Київ, Україна
Резюме: Синтезовано та перевірено на протигрибкову активність низку 1,3-тіазол-2-іл гідразидів ароматичних альдегідів. Серед досліджених
сполук – дві виглядають найбільш перспективно: 2-[(1Z)-[2-(4-метил-1,3-тіазол-2-іл)гідразин-1-іліден]метил]піридин маючи значення МІК рівне
8 мкг/мл щодо Cryptococcus neoformans та МІК – 16 мкг/мл щодо Candida albicans, а також 4-[(1Z)-{2-[4-(2,4-дихлорофеніл)-1,3-тіазол-2-
іл]гідразин-1-іліден}метил]-2,6-диметоксифенол маючи МІК 0.5 мкг/мл проти Cryptococcus neoformans.
Ключові слова: 1,3-тіазол-2-іл гідразон; протигрибкова активність; Cryptococcus neoforma; Candida albicans.
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| id | oai:ojs2.bioorganica.com.ua:article-90 |
| institution | Ukrainica Bioorganica Acta |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-20T01:01:33Z |
| publishDate | 2024 |
| publisher | V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine |
| record_format | ojs |
| resource_txt_mv | bioorganicacomua/dd/76136d86d8ed64c922e4f3df43d789dd.pdf |
| spelling | oai:ojs2.bioorganica.com.ua:article-902026-07-19T14:56:55Z Synthesis and study of antifungal activity of aromatic aldehyde 1,3-thiazol-2-yl hydrazones Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів Tarnavskiy, Sergiy S. Lukashov, Sergiy S. Bdzhola, Volodymyr G. Voitiuk, Volodymyr V. Yarmoluk, Sergiy M. 1,3-thiazol-2-yl hydrazone antifungal activity Cryptococcus neoformans Candida albicans 1,3-тіазол-2-іл гідразон протигрибкова активність Cryptococcus neoformans Candida albicans A number of 1,3-thiazol-2-yl hydrazones of aromatic aldehydes were synthesized and tested for antifungal activity. It was found two promising compounds: 2-[(1Z)-[2-(4-methyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]methyl]pyridine has MIC of 8 μg/ml against Cryptococcus neoformans and MIC of 16 μg/ml against Candida albicans and 4-[(1Z)-{2-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]hydrazin-1-ylidene}methyl]-2,6-dimethoxy-phenol has MIC of 0.5 μg/ml against Cryptococcus neoformans, respectively Синтезовано та перевірено на протигрибкову активність низку 1,3-тіазол-2-іл гідразидів ароматичних альдегідів. Серед досліджених сполук – дві виглядають найбільш перспективно: 2-[(1Z)-[2-(4-метил-1,3-тіазол-2-іл)гідразин-1-іліден]метил]піридин маючи значення МІК рівне 8 мкг/мл щодо Cryptococcus neoformans та МІК – 16 мкг/мл щодо Candida albicans, а також 4-[(1Z)-{2-[4-(2,4-дихлорофеніл)-1,3-тіазол-2-іл]гідразин-1-іліден}метил]-2,6-диметоксифенол маючи МІК 0.5 мкг/мл проти Cryptococcus neoformans V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2024-12-30 Article Article application/pdf https://bioorganica.com.ua/index.php/journal/article/view/90 10.15407/bioorganica2024.02.037 Ukrainica Bioorganica Acta; Vol. 19 No. 2 (2024): Ukrainica Bioorganica Acta; 37-40 Ukrainica Bioorganica Acta; Том 19 № 2 (2024): Ukrainica Bioorganica Acta; 37-40 1814-9766 1814-9758 10.15407/bioorganica2024.02 en https://bioorganica.com.ua/index.php/journal/article/view/90/89 Copyright (c) 2024 Sergiy S. Tarnavskiy, Sergiy S. Lukashov, Volodymyr G. Bdzhola, Volodymyr V. Voitiuk, Sergiy M. Yarmoluk https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | 1,3-тіазол-2-іл гідразон протигрибкова активність Cryptococcus neoformans Candida albicans Tarnavskiy, Sergiy S. Lukashov, Sergiy S. Bdzhola, Volodymyr G. Voitiuk, Volodymyr V. Yarmoluk, Sergiy M. Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів |
| title | Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів |
| title_alt | Synthesis and study of antifungal activity of aromatic aldehyde 1,3-thiazol-2-yl hydrazones |
| title_full | Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів |
| title_fullStr | Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів |
| title_full_unstemmed | Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів |
| title_short | Синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів |
| title_sort | синтез та вивчення протигрибкової активності похідних 1,3-тіазол-2-іл гідразидів ароматичних альдегідів |
| topic | 1,3-тіазол-2-іл гідразон протигрибкова активність Cryptococcus neoformans Candida albicans |
| topic_facet | 1,3-thiazol-2-yl hydrazone antifungal activity Cryptococcus neoformans Candida albicans 1,3-тіазол-2-іл гідразон протигрибкова активність Cryptococcus neoformans Candida albicans |
| url | https://bioorganica.com.ua/index.php/journal/article/view/90 |
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