4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин
Sulfonamide derivatives of 3-phenyl-1H-isochromen-1-one were synthesized by reaction of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride with amines. The specific parameters of chlorosulfonation of 3-phenyl-1H-isochromen-1-one have been identified; the procedure for synthesis of 4-(1-oxo-1H-isoc...
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V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
2021
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|---|---|
| author | Hlotov, Serhii V. Shablykina, Olga V. Khilya, Volodymyr P. |
| author_facet | Hlotov, Serhii V. Shablykina, Olga V. Khilya, Volodymyr P. |
| author_institution_txt_mv | [
{
"author": "Serhii V. Hlotov",
"institution": "Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine"
},
{
"author": "Olga V. Shablykina",
"institution": "Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine"
},
{
"author": "Volodymyr P. Khilya",
"institution": "Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine"
}
] |
| author_sort | Hlotov, Serhii V. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-19T14:56:53Z |
| description | Sulfonamide derivatives of 3-phenyl-1H-isochromen-1-one were synthesized by reaction of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride with amines. The specific parameters of chlorosulfonation of 3-phenyl-1H-isochromen-1-one have been identified; the procedure for synthesis of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride and its by-product (disulfochloride) was optimized. The evaluation of anticancer activity of obtained sulfonamides showed no appreciable cytotoxicity |
| doi_str_mv | 10.15407/bioorganica2021.02.030 |
| first_indexed | 2025-07-17T12:19:31Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2021, Vol. 16, N 2
UDC 547.814.5+547.541.521+615.277
DOI: https://doi.org/10.15407/bioorganica2021.02.030
30
Ukrainica Bioorganica Acta
www.bi oorgan ica .org .ua
SHORT COMMUNICATION
4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonamides and their effect
on cancer cell growth
Serhii V. Hlotov, Olga V. Shablykina*, Volodymyr P. Khilya
Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv, 01601, Ukraine
Abstract: Sulfonamide derivatives of 3-phenyl-1H-isochromen-1-one were synthesized by reaction of 4-(1-oxo-1H-isochromen-3-
yl)benzenesulfonyl chloride with amines. The specific parameters of chlorosulfonation of 3-phenyl-1H-isochromen-1-one have been
identified; the procedure for synthesis of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride and its by-product (disulfochloride) was
optimized. The evaluation of anticancer activity of obtained sulfonamides showed no appreciable cytotoxicity.
Keywords: 3-phenyl-1H-isochromen-1-one; chlorosulfonation; 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonamides; cancer cells.
Introduction
Sulfonamides belong to a crucial class of organic
compounds which show a wide range of biological
activities. They are verified to be an interesting scaffold
that holds a wide variety of biological activities including
anticancer, antimicrobial, antimalarial, and antiviral
activities [1]. Some examples of new antibacterial
heterocyclic sulfonamides (Figure 1) were presented in a
critical review [2], and various aspects of their structure-
activity relationship (SAR) were discussed.
Although sulfonamides are well-known for their anti-
bacterial activity, some of these compounds with hetero-
cyclic ring are an important group of potential anticancer
agents [3, 4]. SAR for this sulfonamides was analyzed in
detail by Wan and coworkers [5].
In the search for new anticancer agents, we were
interested in previously unstudied sulfonamides with
anisocoumarin (1H-isochromen-1-one) fragment.
Received:
Revised:
Accepted:
Published online:
15.10.2021
29.10.2021
30.11.2021
30.12.2021
Corresponding author. Tel.: +380-66-167-9812;
e-mail: shablykina@ukr.net (O. V. Shablykina)
ORCID: 0000-0002-5362-0831
Previously, we presented a method for constructing
sulfonamides based on 3-phenylisocoumarin 1 (Scheme 1)
by chlorosulfonation and subsequent reaction of the
resulting sulfochloride 2 with amines [6, 7]. In this
communication we describe a synthesis of new derivatives
of isocoumarin 1 and a preliminary assessment of their
anticancer activity.
Figure 1. Reported sulfonamides as potentially bioactive
compounds [3, 4].
© Hlotov S. V. 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.
https://orcid.org/0000-0001-5556-9147
S. V. Hlotov, O. V. Shablykina, V. P. Khilya
31
Results and Discussion
The synthetic part of the work confirmed the efficiency
of using 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl
chloride (2). This substrate is active enough to react
with a wide variety of amines. It can be stored for quite
a long time at room temperature. Chlorosulfonation of
3-phenylisocoumarin led to only one by-product 3
(disulfonyl chloride 3). This side reaction can be easily
avoided by a temperature control. We found that product 3
was formed in a significant amount only at temperature
above 70 °C. When temperature was lowered to 55 °C the
formation of sulfonyl chloride 2 was found as the only
reaction product.
Scheme 1. Chlorosulfonation of 3-phenylisocoumarin 1 by
chlorosulfonic acid.
The ratio of mono- and dichlorosulfonation of 3-phenyl-
isocoumarin under various reaction conditions is presented
below (Table 1).
Table 1. The influence of reaction condition on the ratio of
products 2 and 3 (Scheme 1).
Reaction condition
(per one gram of 1)
Product 2,
%
Product 3,
%
2 mL HOSO2Cl, 55 °С, 2 h 100 –
2 mL HOSO2Cl, 70 °С, 12 h 60 40
10 mL HOSO2Cl, 110 °С, 20 h – 100*
* excluding non-identifiable decomposition material
Unfortunately, the targeted formation of disulfonyl
chloride 3 was accompanied by a significant decomposition
that yielded only 20% of chloride 3 (see Experimental part).
Sulfonamides 4 were synthesized in an acetonitrile
solution in the presence of pyridine as a base (Scheme 2).
Previously, we obtained similar sulfamides in 1,4-dioxane
with Et3N as a base [6, 7]. It is worth noting that both
methods are equally effective to synthesize amides with
excellent yields.
An effect on the cancer cells growth was investigated for
sulfamides 4c,e,f, as well as for previously obtained leucine
derivatives 4g and 5 (Figure 2). Acid 5 is formed upon
hydrolysis of both the ester and lactone moieties of
compound 4g; such ring-closure reaction for water-soluble
sulfonamides 4 occurs readily and can takes place in a
biological medium [7].
Scheme 2. Synthetic pathway of sulfonamides 4a-f.
Figure 2. Some novel leucine sulfonamide derivatives.
The in vitro evaluation of the antitumor activity for the
obtained heterocyclic compounds was performed on a panel
of 60 cell lines obtained from nine types of cancer [8].
Unfortunately, the investigated sulfonamides did not exhibit
a significant antiproliferative activity. The average value of
the GP parameter (percent of cancer cell growth in 10-5 M
solution of the test compound) was in the range of
95-104%. A comparison of the biological effect of
isocoumarin 4g and acid 5 showed that, at least in this case,
the opening of the isocoumarin ring did not lead to an
increase of biological activity: the GP value of acid 5 was
slightly higher than that of lactone 4g (104 and 95%,
respectively), while the spread of values was smaller (57%
for acid 5 and 91% for lactone 4g).
Two similar effects for all the studied substances was
found, which, in our opinion, can be useful information for
planning further studies of biological activity of similar
compounds. Firstly, sulfonamides 4c,e-g and 5 can inhibit
the growth of breast cancer cells more perceptible compared
to other lines. For example, the GP value of the MCF7 cell
line under the action of an ortho-toluidine derivative 4f was
35%, and that of the fluorine-containing amide 4c was 38%.
Secondly, these substances tended to accelerate the growth
of kidney cancer cells. Thus, the GP index of the TK-10 cell
line under exposure to sulfanilamide 4f was 170% while the
GP index for the compound 4c was 157%.
ISSN 1814-9758. Ukr. Bioorg. Acta, 2021, Vol. 16, N 2
32
Conclusions
The series of amides of 3-phenylisocoumarins were
synthesized and tested on their antiproliferative activity.
3-Phenylisocoumarins with a sulfonamide group in the
position 4' didn't show any significant inhibitory effect on
the growth of cancer cells lines. However, considering a
number of published studied of sulfonamide molecules in
relation to anticancer activity present the opportunity to
screen these molecules for other biological activity.
Experimental section
All solvents were purified according to the standard
procedures. All materials were purchased from commercial
sources and used without further purification. NMR spectra
were recorded on a Mercury-400 spectrometer (400 MHz
for 1H and 100 MHz for 13C) and Bruker 170 spectrometer
(500 MHz for 1H and 126 MHz for 13C). Chemical shifts are
reported in ppm downfield from TMS as internal standards.
Melting points were determined using a Kofler-type Leica
Galen III micro hot stage microscope. Mass spectra were
recorded on an LC-MS instrument with chemical ionization
(CI). LC-MS data were acquired on an Agilent 1200 HPLC
system equipped with DAD/ELSD/LCMS-6120 diode
matrix and mass-selective detector. Elemental analyses for
C, H, and N were conducted using Perkin-Elmer C, H, N
Analyzer, their results were found to be in good agreement
(±0.4%) with the calculated values.
Synthesis
4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonyl chlori-
de (2).
To 10 mL of chlorosulfonic acid at 0 °C with stirring
5.00 g (0.022 mol) of 3-phenylisocoumarin (1) was added
slowly and gradually. The reaction mixture was heated to
55 °C and was stirred at this temperature for 2 h. Then the
mixture was cooled down to room temperature and poured
at 250 g of ice (caution! very exothermic and rapid
hydrolysis). The precipitate was filtered off and dried from
residual water in the vacuum oven at 65 °C. Yield: 5.63 g,
78%. (Alternative procedure of sulfonyl chloride 2
obtaining as well as spectra data was also described in [6]).
3-(4-(Chlorosulfonyl)phenyl)-1-oxo-1H-isochromene-7-
sulfonyl chloride (3).
To 10 mL of chlorosulfonic acid at 0 °C with stirring
1.00 g (4.5 mmol) of 3-phenylisocoumarin (1) was added
slowly and gradually. The reaction mixture was heated to
110 °C and was stirred at this temperature for 20 h. Then
the mixture was cooled down to room temperature and
poured at 250 g of ice (caution! very exothermic and rapid
hydrolysis). The precipitate was filtered off and dissolved in
150 mL EtOAc; this solution was washed with water
(2100 mL) and brine (50 mL), dried over Na2SO4, and
evaporated in vacuo. Yield: 380 mg, 20%; mp 205 °C
(decomp.).1H NMR (400 MHz, CDCl3) δ 8.98 (d, J 1.8 Hz,
1H, H-8), 8.34 (dd, J 7.6, 1.8 Hz, 1H, H-6), 8.20-8.12 (m,
4H, H-2',3',5',6'), 7.79 (d, J 7.6 Hz, 1H, H-5), 7.20 (s, 1H,
H-4). 13C NMR (100 MHz, CDCl3) δ 161.4, 150.7, 144.6,
138.4, 136.4, 135.3, 130.0, 129.6, 127.72, 126.7, 126.12,
121.1, 105.3. HPLC (CI) m/z (M+H)+ 383 (corresponding
disulfoacid was registered).
General procedure for the synthesis of sulfonami-
des 4a-f.
To the solution of 240 mg (0.75 mmol) of sulfonyl
chloride 2 in 20 mL of CH3CN 0.825 mmol of correspon-
ding amine and 2-3 drops of pyridine were added. The
reaction mixture was stirred at the room temperature for
12 h. Then the solvent was evaporated in vacuo, the residue
was washed with 2М aq. НСl, and recrystallized from
isopropyl alcohol (5-10 mL).
3-(4-(Morpholinosulfonyl)phenyl)-1H-isochromen-1-one
(4a).
Yield: 201 mg, 72%; mp 189-190 °C. 1H NMR (500
MHz, DMSO-d6) δ 8.21 (d, J 8.0 Hz, 1H, H-8), 8.18 (d,
J 8.2 Hz, 2H, H-3',5'), 7.95-7.86 (m, 3H, H-6,2',6'),
7.79-7.74 (m, 2H, H-4,5), 7.67 (t, J 7.4 Hz, 1H, H-7), 3.64
(br s, 4H, O(CH2)2), 2.92 (br s, 4H, N(CH2)2). 13C NMR
(126 MHz, DMSO-d6) δ 160.8, 150.4, 136.6, 135.9, 135.4,
135.1, 129.2, 128.9, 128.22, 126.9, 125.62, 120.2, 104.5,
65.12 (O(CH2)2), 45.72 (N(CH2)2). HPLC (CI) m/z
(M+H)+ 372.
3-(4-((4-Ethylpiperazin-1-yl)sulfonyl)phenyl)-1H-iso-
chromen-1-one (4b).
Yield: 227 mg, 76%, mp 175-176 °C. 1H NMR (500
MHz, DMSO-d6) δ 8.21 (d, J 7.9 Hz, 1H, H-8), 8.16 (d,
J 8.4 Hz, 2H, H-3',5'), 7.93-7.85 (m, 3H, H-6,2',6'), 7.78-
7.72 (m, 2H, H-4,5), 7.66 (t, J 7.4 Hz, 1H, H-7), 2.93 (br s,
4Н, 2СН2), 2.41 (br s, 4Н, 2СН2), 2.29 (q, J 7.1 Hz, 2H,
CH2CH3), (t, J 7.1 Hz, 3H, CH3). HPLC (CI) m/z (M+H)+
399.
3-(4-((4,4-Difluoro-3,5-dimethylpiperidin-1-yl)sulfonyl)-
phenyl)-1H-isochromen-1-one (4c).
Yield: 263 mg, 81%, mp 177-178 °C. 1H NMR (500
MHz, DMSO-d6) δ 8.21 (d, J 7.6 Hz, 1H, H-8), 8.17 (d,
J 7.8 Hz, 2H, H-3',5'), 7.97-7.87 (m, 3H, H-6,2',6'), 7.79-
7.73 (m, 2H, H-4,5), 7.67 (t, J 7.2 Hz, 1H, H-7), 3.37-3.30
(m, 2H, CH2), 2.78-2.67 (m, 2H, CH2), 2.27-2.13 (m, 2H,
2CH), 0.98 (d, J 4.6 Hz, 3H, CH3), 0.93 (d, J 4.6 Hz,
3H, CH3). 13C NMR (126 MHz, DMSO-d6) δ 161.1,
150.7, 145.5, 142.72, 136.9, 136.3, 136.2, 135.7, 129.5,
128.21 (t, J 118.9 Hz), 127.1, 126.02, 120.5, 104.9, 49.37
(d, J 8.9 Hz, CH2), 46.16 (d, J 7.7 Hz, CH2), 37.23 (t,
J 23.3 Hz, CH), 34.75 (t, J 24.1 Hz, CH), 8.962 (d, J 15.7
Hz, 2CH3). HPLC (CI) m/z (M+H)+ 434.
N-Methyl-4-(1-oxo-1H-isochromen-3-yl)-N-(prop-2-yn-
1-yl)benzenesulfonamide (4d).
Yield: 177 mg, 67%; mp 186-187 °C. 1H NMR (400
MHz, DMSO-d6) δ 8.21 (d, J 7.6 Hz, 1H, H-8), 8.14 (d,
J 8.0 Hz, 2H, H-3',5'), 7.98-7.88 (m, 3H, H-6,2',6'), 7.78-
7.72 (m, 2H, H-4,5), 7.66 (t, J 7.6 Hz, 1H, H-7), 4.08 (s,
S. V. Hlotov, O. V. Shablykina, V. P. Khilya
33
2H, СН2), 3.15 (s, 1H, СН), 2.79 (s, 3H, СН3). 13C NMR
(126 MHz, DMSO-d6) δ 161.0, 150.7, 137.4, 136.8, 135.8,
135.6, 129.3, 129.0, 128.42, 127.0, 125.52, 120.3, 104.6,
78.9 (C), 76.78 (C), 36.9 (CH2), 34.20 (CH3). HPLC (CI)
m/z (M+H)+ 354.
N-Benzyl-4-(1-oxo-1H-isochromen-3-yl)benzenesulfon-
amide (4e).
Yield: 238 mg, 81%; mp 197-198 °C. 1H NMR (400
MHz, DMSO-d6) δ 8.21 (d, J 7.6 Hz, 1H, H-8), 8.15 (br s,
1H, NH), 8.10 (d, J 8.4 Hz, 2H, H-3',5'), 7.97-7.87 (m, 3H,
H-6,2',6'), 7.76 (d, J 7.6 Hz, 1H, H-5), 7.70 (s, 1H, H-4),
7.66 (t, J 7.6 Hz, 1H, H-7), 7.30-7.20 (m, 5H, Ph), 4.04 (s,
2H, CH2). 13C NMR (100 MHz, DMSO-d6) δ 161.1, 150.9,
141.6, 137.6, 136.9, 135.6, 135.1, 134.3, 129.3, 129.02,
128.42, 127.32, 127.2, 127.0, 125.62, 120.3, 104.3, 46.2
(CH2). HPLC (CI) m/z (M+H)+ 392.
4-(1-Oxo-1H-isochromen-3-yl)-N-(o-tolyl)benzene-
sulfonamide (4f).
Yield: 244 mg, 83%; mp 194-195 °C. 1H NMR (400
MHz, DMSO-d6) δ 9.68 (s, NН), 8.20 (d, J 7.6 Hz, 1H,
H-8), 8.08 (d, J 8.4 Hz, 2H, H-3',5'), 7.90 (t, J 7.6 Hz, 1H,
H-6), 7.79 (d, J 8.4 Hz, 2H, H-2',6'), 7.74 (d, J 7.6 Hz, 1H,
H-5), 7.70-7.61 (m, 2H, H-4,7), 7.18-7.07 (m, 3H, Tol),
7.01-6.93 (m, 1H, Tol), 2.02 (s, 3H, СН3). 13C NMR (126
MHz, DMSO-d6) δ 160.9, 150.7, 141.3, 136.7, 135.5, 135.3,
134.6, 134.4, 130.8, 129.3, 128.9, 127.32, 127.0, 126.62,
126.4, 125.52, 120.3, 104.4, 17.6 (CH3). HPLC (CI) m/z
(M+H)+ 392.
Biological Assay
The anticancer activity of synthesized compounds was
tested according to the International Program of the
National Institutes of Health – DTP (Developmental
Therapeutic Program) of the National Cancer Institute
(NCI, Bethesda, Maryland, USA) on 60 cancer cell lines
[8]; a description of the technique is also given in [9].
Notes
Acknowledgments and finances. We would like to
thank US Public Health Service and National Cancer
Institute, USA, for in vitro evaluation of anticancer
activity (providing the NCI-60 cell testing) within the
framework of Developmental Therapeutic Program
(http://dtp.cancer.gov), and Enamine Ltd. for the material
and technical support for the synthetic part of this work.
Disclaimer. This material should not be interpreted as
representing the viewpoint of the U.S. National Institutes of
Health, or the National Cancer Institute.
The authors declare no conflict interest.
References
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containing heterocyclic derivatives and its structure-activity
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S. A.; Khilya V. P. Amino acid sulfonamides based on 4-(1-oxo-1H-
isochromen-3-yl)benzenesulfonyl chloride. Ukr. Bioorg. Acta, 2020,
15, 27-32.
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(accessed on October 15, 2021).
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4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія
на ріст ракових клітин
С. В. Глотов, О. В. Шабликіна*, В. П. Хиля
Київський національний університет імені Тараса Шевченка, вул. Володимирська, 60, Київ, 01601, Україна
Резюме: Ряд сульфонамідних похідних 3-феніл-1Н-ізохромен-1-ону синтезовано взаємодією 4-(1-оксо-1Н-ізохромен-3-
іл)бензолсульфонілхлориду з амінами. З’ясовано особливості сульфохлорування вихідної сполуки (3-феніл-1Н-ізохромен-1-он); оптимізовано
процедуру синтезу 4-(1-оксо-1H-ізохромен-3-іл)бензенсульфонілхлориду та його побічного продукту (дисульфохлориду). Первинна оцінка
отриманої протипухлинної активності сульфаніламідів не виявила помітної цитотоксичності.
Ключові слова: 3-феніл-1H-ізохромен-1-он; сульфохлорування; 4-(1-оксо-1H-ізохромен-3-іл)бензенсульфонаміди; ракові клітини.
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| institution | Ukrainica Bioorganica Acta |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-20T01:00:37Z |
| publishDate | 2021 |
| publisher | V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine |
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| resource_txt_mv | bioorganicacomua/0f/c726cea511bb77673d6142e3f349a00f.pdf |
| spelling | oai:ojs2.bioorganica.com.ua:article-242026-07-19T14:56:53Z 4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonamides and their effect on cancer cell growth 4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин Hlotov, Serhii V. Shablykina, Olga V. Khilya, Volodymyr P. 3-phenyl-1H-isochromen-1-one sulfochlorination; 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonamides cancer cells 3-феніл-1H-ізохромен-1-он сульфохлорування 4-(1-оксо-1H-ізохромен-3-іл)бензенсульфонаміди ракові клітини Sulfonamide derivatives of 3-phenyl-1H-isochromen-1-one were synthesized by reaction of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride with amines. The specific parameters of chlorosulfonation of 3-phenyl-1H-isochromen-1-one have been identified; the procedure for synthesis of 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonyl chloride and its by-product (disulfochloride) was optimized. The evaluation of anticancer activity of obtained sulfonamides showed no appreciable cytotoxicity Ряд сульфонамідних похідних 3-феніл-1Н-ізохромен-1-ону синтезовано взаємодією 4-(1-оксо-1Н-ізохромен-3-іл)бензолсульфонілхлориду з амінами. З’ясовано особливості сульфохлорування вихідної сполуки (3-феніл-1Н-ізохромен-1-он); оптимізовано процедуру синтезу 4-(1-оксо-1H-ізохромен-3-іл)бензенсульфонілхлориду та його побічного продукту (дисульфохлориду). Первинна оцінка отриманої протипухлинної активності сульфаніламідів не виявила помітної цитотоксичності. V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2021-12-27 Article Article application/pdf https://bioorganica.com.ua/index.php/journal/article/view/24 10.15407/bioorganica2021.02.030 Ukrainica Bioorganica Acta; Vol. 16 No. 2 (2021): Ukrainica Bioorganica Acta; 30-33 Ukrainica Bioorganica Acta; Том 16 № 2 (2021): Ukrainica Bioorganica Acta; 30-33 1814-9766 1814-9758 10.15407/bioorganica2021.02 en https://bioorganica.com.ua/index.php/journal/article/view/24/29 Copyright (c) 2021 Serhii V. Hlotov, Olga V. Shablykina, Volodymyr P. Khilya https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | 3-феніл-1H-ізохромен-1-он сульфохлорування 4-(1-оксо-1H-ізохромен-3-іл)бензенсульфонаміди ракові клітини Hlotov, Serhii V. Shablykina, Olga V. Khilya, Volodymyr P. 4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин |
| title | 4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин |
| title_alt | 4-(1-Oxo-1H-isochromen-3-yl)benzenesulfonamides and their effect on cancer cell growth |
| title_full | 4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин |
| title_fullStr | 4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин |
| title_full_unstemmed | 4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин |
| title_short | 4-(1-Оксо-1Н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин |
| title_sort | 4-(1-оксо-1н-ізохромен-3-іл)бензолсульфонаміди та їхня дія на ріст ракових клітин |
| topic | 3-феніл-1H-ізохромен-1-он сульфохлорування 4-(1-оксо-1H-ізохромен-3-іл)бензенсульфонаміди ракові клітини |
| topic_facet | 3-phenyl-1H-isochromen-1-one sulfochlorination 4-(1-oxo-1H-isochromen-3-yl)benzenesulfonamides cancer cells 3-феніл-1H-ізохромен-1-он сульфохлорування 4-(1-оксо-1H-ізохромен-3-іл)бензенсульфонаміди ракові клітини |
| url | https://bioorganica.com.ua/index.php/journal/article/view/24 |
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