Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин
In different conditions, from 3-acetyl-1H-isochromen-1-one three partial reduction products were obtained, namely 3-(1-hydroxyethyl)-1H-isochromen-1-one, 3-(1-hydroxyethyl)isochroman-1-one, and 3-ethylisochroman-1-one. The influence of two products with an alcohol fragment, as well as 4-hydroxy-1,2,...
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V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
2024
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| author | Shablykin, Oleh V. Shablykina, Olga V. Tarasiuk, Ilona Yu. |
| author_facet | Shablykin, Oleh V. Shablykina, Olga V. Tarasiuk, Ilona Yu. |
| author_institution_txt_mv | [
{
"author": "Oleh V. Shablykin",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Olga V. Shablykina",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine; Taras Shevchenko National University of Kyiv, Kyiv, Ukraine"
},
{
"author": "Ilona Yu. Tarasiuk",
"institution": "Taras Shevchenko National University of Kyiv, Kyiv, Ukraine "
}
] |
| author_sort | Shablykin, Oleh V. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-19T14:56:55Z |
| description | In different conditions, from 3-acetyl-1H-isochromen-1-one three partial reduction products were obtained, namely 3-(1-hydroxyethyl)-1H-isochromen-1-one, 3-(1-hydroxyethyl)isochroman-1-one, and 3-ethylisochroman-1-one. The influence of two products with an alcohol fragment, as well as 4-hydroxy-1,2,3,4-tetrahydro-6H-benzo[c]chromen-6-one, on the growth of cancer cells was investigated through One Doses Full NCI 60 Cell Panel Assay. The only one significant effect was found: 3-(1-hydroxyethyl)-1H-isochromen-1-one practically stops the growth of CCRF-CEM cell lines (Leukemia) |
| doi_str_mv | 10.15407/bioorganica2024.02.033 |
| first_indexed | 2025-07-17T12:20:03Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2024, Vol. 19, N 2
UDC 547.814.5
DOI: https://doi.org/10.15407/bioorganica2024.02.033
33
SHORT COMMUNICATION
Preliminary evaluation of the effect of partially hydrogenated
3-acetylisocoumarin derivatives on the cancer cells growth
Oleh V. Shablykin1, Olga V. Shablykina1,2*, Ilona Yu. Tarasiuk2
1V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine
2 Taras Shevchenko National University of Kyiv, Kyiv, Ukraine
Abstract: In different conditions, three partial reduction products were obtained from 3-acetyl-1H-isochromen-1-one, namely
3-(1-hydroxyethyl)-1H-isochromen-1-one, 3-(1-hydroxyethyl)isochroman-1-one, and 3-ethylisochroman-1-one. The influence of two
products with an alcohol fragment, as well as 4-hydroxy-1,2,3,4-tetrahydro-6H-benzo[c]chromen-6-one, on the growth of cancer cells
was investigated through One Doses Full NCI 60 Cell Panel Assay. The only one significant effect was found: 3-(1-hydroxyethyl)-
1H-isochromen-1-one practically stops the growth of CCRF-CEM cell lines (Leukemia).
Keywords: 3-acetyl-1H-isochromen-1-one (3-acetylisocoumarin); reduction; cancer cells.
Introduction
The modification of bioactive natural compounds and the
synthesis of their analogues remains an applicable and
productive direction in the search for new medicines [1, 2].
Isocoumarins and their hydrogenated derivatives are among
the many examples of natural compounds which are so
interesting to drug developers. Thus, inspired by the
structure of the natural antitumor antibiotic Cytogenin [3],
the authors [4] created a number of isocoumarins and
3,4-dihydroisocoumarins with a polar group in position 3
(Figure 1a) and investigated their antiproliferative activity.
The alcohol 1 showed the ability to inhibit the growth of
cancer cells.
In another study [5], the structure of Cladosporin [6],
known primarily for its antimalarial activity, was modified
to improve medical properties. Among the diversity of
modifications, the most useful for antimalarial activity
Received:
Revised:
Accepted:
Published online:
17.09.2024
28.10.2024
29.11.2024
30.12.2024
Corresponding author. Tel.: +380-66-167-9812;
e-mail: shablykina@ukr.net (O.V. Shablykina)
ORCID: 0000-0002-5362-0831
was the addition of a hydroxyl group into the methylene
linker (compound 2, Figure 1b).
Molecular docking in the work [4] and X-ray study of
the substances-enzyme complex in the work [5] showed that
both the hydroxyl group and the sp3-hybridization of the
carbon in position 3 of isocoumarin are important for
effective binding. Thus, 3,4-dihydroisocoumarins with a
hydroxyalkyl fragment in position 3 can reasonably be
considered a promising class of substances from the side of
their biological activity.
There are no many approaches to the synthesis of
3-(hydroxyalkyl)-3,4-dihydroisocoumarins.
For example, in the study [4], substance 1 was
synthesized by catalytic hydrogenation of the corresponding
isocoumarin 3 (Scheme 1a), and the last one was obtained
by the cyclization of an alkyne with an ortho-
carboxyphenyl substituent (this method is very popular in
the isocoumarins' chemistry). Another interesting reaction,
i.e. the oxidation of the double bond and the subsequent
closing of the isochromanone system (Scheme 1b), was
used for the synthesis of one of the objects for biological
research in the study [5].
Another obvious option for obtaining 3-(hydroxylalkyl)-
3,4-dihydroisocoumarins through the stage of the
corresponding isocoumarins is the reduction of.
© Shablykin O.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.
Ukrainica Bioorganica Acta
www.bi oorgan ica .org .ua
ISSN 1814-9758. Ukr. Bioorg. Acta, 2024, Vol. 19, N 2
34
Figure 1. The examples of structural modification of natural isocoumarins and 3,4-dihydroisocoumarins for novel bioactive substances
discovery.
3-acylisocoumarins. Surprisingly, there are not much
information about 3-acylisocoumarins reduction in
literature, and the most useful for us was the synthesis
tricyclic condensed structure 6 with an alcohol group
(Scheme 1c) [7].
OH
I
O
OH
MeO
MeO O
O
OH
RR
O
MeO
MeO
OMe 1. OsO4, NMO
2. aq Na2SO3
R = tetrahydro-2H-pyran-2-yl 4 (56%)
a)
b)
CuI, K2CO3, trans-
4-hydroxy-L-proline
O
O
OH
3 (54%)
H2 (250 psi) O
O
OH
1 (98%)
Pd / C
c)
O
O
O
O
O
OH
6 (85%)5
MeOH
NaBH4 (3 eq)
Scheme 1. Approaches to the synthesis of 3-(hydroxyalkyl)-3,4-
dihydroisocoumarins.
As demonstrated in literature [8], 3-acylisocoumarins are
quite synthetically accessible substances, but their potential
as substrates for further transformations has not been
realized so far. This is also true for reduction reactions:
3-acylisocoumarins have at least three fragments capable of
reduction, and it is possible to obtain a number of different
products on the basis of one substrate; especially taking into
account the possibility of different levels of reduction and
both saving and opening of the cycle.
To understand the prospects of this direction, we aimed
to investigate the effect of various reducing agents on
3-acetylisocoumarin and evaluate the impact of reduced
derivatives on cancer cells.
Results and Discussion
Reduction of 3-acetylisocoumarin 7 with NaBH4 under
mild conditions, similar to those described in the literature
for this reaction earlier [7], expectedly led to isocoumarin 8
(Scheme 2a). The synthesis of the tricyclic derivative 7
(Scheme 1c) was also reproduced using this technique with
minor variations. Note that the structure of product 6
executes significant restrictions on the conformational
mobility of the OH group compared to compound 8.
A more forceful reduction of isocoumarin 7 is
hydrogenation at high temperature and pressure with
Pd(OH)2 / C catalyst. This yields a mixture of compounds
(Scheme 2b): 3,4-dihydroisocoumarin 9 with 1-hydroxy-
ethyl fragment, which is a homologue of the bioactive
primary alcohol 1 (see Figure 1a above), and 3,4-dihydro-
isocoumarin 10 with ethyl substituent. Products 9 and 10
were separated chromatographically, compound 9 with two
asymmetric centres was isolated as 1:1 diastereomeric
mixture.
O
O
O
Me
O
O
OH
Me8 (82%)7
O
O
OH
Me9 (34%)
7 +
O
O
Me10 (30%)
a)
b)
MeOH,
50°C, 12 h
20% Pd(OH)2 / C
(cat.), H2 (40 atm)
NaBH4 (excess)
MeOH, rt, 2-3 h;
then NaHCO3 aq
Scheme 2. Reduction of 3-acetylisocoumarin under different
conditions.
Three compounds were selected for research at the
National Cancer Institute (NCI, Bethesda, Maryland, USA)
(Table 1). A single-dose test of effect of racemic products 6,
8 and diastereomeric mixture 9 on cancer cell growth
O.V. Shablykin et al.
35
brought disappointing results: two out of three samples had
no noteworthy effect on all cell lines. Table 1 shows their
Mean Growth Percent (MGP) values for 60 cancer lines,
and all of them are close to 100%. Moreover, the Delta
values (the difference between the MGP and the GP value
of the most inhibited cell line) of these compounds are also
low, indicating the absence of any significant effect on the
growth of all types of cancer cells. Only isocoumarin 8
showed the ability to inhibit the growth of one of the
investigated leukemia lines selectively and almost
completely (for CCRF-CEM cells the GP was 1.2%), while
not causing a significant effect on the growth of other cell
lines (Table 1).
The biggest surprise was the absence of activity in
3,4-dihydroisocoumarin 9, because the difference in its
structure from compound 1 isn't big. On the other hand: a
previous study [4] used other parameters to evaluate the
anticancer activity for compound 1, and it was also inactive
against some types of cancer cells.
Table 1. Percent of cancer cell growth in 1 x 10–5 M
solution of the test compound compared to the control
(according to One Doses Full NCI 60 Cell Panel Assay).
Com-
pound
NSC Number Mean Growth
Percent, %
Delta, %
6 831590 103.0 13.7
8 831592 99.6 98.5 a
9 833505 112.3 19.3
a GP = 1.2 % for CCRF-CEM (Leukemia).
Conclusions
It can be concluded that the reductions of 3-acyl-
isocoumarins really have a significant synthetic potential,
because depending on the reaction conditions different
degrees of saturation can be achieved and different types of
products can be obtained. However, anticancer activity was
recorded only for one substance to a single cancer line; even
a substance similar in structure to the known anticancer
agent did not show activity. Such a significant effect of
small structural changes on bioactivity requires further
research to obtain a larger number of products with various
structural variations, and motivates us to continue
researching the processes of isocoumarin derivatives
reduction.
Experimental section
All reagents and solvents were purchased from Enamine
Ltd. (www.enamine.net). TLC characterization was
performed with pre-coated silica gel GF254 (0.2 mm). For
column flash chromatography Silica gel 230-400 mesh was
used. NMR spectra of the obtained products were recorded
on a Varian Unity Plus 400 spectrometer (400 MHz for 1H,
101 MHz for 13C); 1H NMR chemical shifts were calibrated
using residual undeuterated DMSO (δ = 2.50 ppm) and
CDCl3 (δ = 7.26 ppm) signals; 13C NMR chemical shifts are
reported relative to the central DMSO (δ = 39.52 ppm) and
CDCl3 (δ = 77.16 ppm) signals. Melting points were
measured on a MPA100 OptiMelt automated melting point
system. Elemental analyses were performed at the
Analytical Laboratory of the V.P. Kukhar Institute of
Bioorganic Chemistry and Petrochemistry of NAS of
Ukraine and be in good agreement (±0.4%) with the
calculated values. LC/MS spectra were recorded on an
Agilent 1100 Series HPLC system equipped with a diode
matrix with an Agilent LC/MS mass selective detector
(chemical ionization).
Synthesis
3-Acetyl-1H-isochromen-1-one (7) was synthesized by
condensation of 2-formylbenzoic acid with chloroacetone in
MeCN solution with Et3N as a base [9]. 2,3-Dihydro-1H-
benzo[c]chromene-4,6-dione (5) was synthesized by
interaction of benzenediazonium 2-carboxylate with
cyclohexane-1,2-dione [7]. Spectral data of ketone 7 see [9],
and ketone 5 see [10].
General method of reduction of the 3-acyl-1H-
isochromen-1-ones.
The initial ketone (5 mmol) was suspended in methanol
(25 mL), and NaBH4 (191 mg, 5 mmol) was added in four
portions at 0 C with stirring in an half of hour. After
finishing the reaction 50 mL of 8% aqueous solution of
NaHCO3 was added. The product was extracted with
CH2Cl2 (3 × 20 mL); organic layer was dried over Na2SO4
and concentrated under reduced pressure.
3-(1-Hydroxyethyl)-1H-isochromen-1-one (8).
Spectral data are in agreement with Ref. [11], where
compound 8 was obtained by Pd-catalyzed coupling of 2-
iodobenzoic acid and but-3-yn-2-ol with following
cyclization.
4-Hydroxy-1,2,3,4-tetrahydro-6H-benzo[c]chromen-6-one
(6).
Yield: 924 mg, 86%; mp 175-176 °C (176-177 °C in Ref.
[7]). 1H NMR (400 MHz, DMSO-d6) δ 8.14 (d, J = 7.8 Hz,
1H), 7.84 (t, J = 7.6 Hz, 1H), 7.63-7.51 (m, 2H), 5.54 (d, J
= 5.6 Hz, 1H), 4.35 (d, J = 4.0 Hz, 1H), 2.64 (br. d, J = 16.5
Hz, 1H), 2.48-2.38 (m, 1H), 1.92-1.68 (m, 4H). 13C NMR
(100 MHz, DMSO-d6) δ 161.5, 152.3, 136.9, 135.1, 128.9,
128.2, 122.7, 120.3, 110.5, 63.2, 31.3, 22.4, 17.0. HPLC
(CI) m/z (M+H)+ 217.
Synthesis of 3-(1-hydroxyethyl)isochroman-1-one (9) and
3-ethylisochroman-1-one (10).
The ketone 7 (1.90 g, 10 mmol) was suspended in
methanol (50 mL), and 0.1 g of Pd(OH)2 / C (20 wt. %) was
added. This mixture was heated (50 °C) and stirred in a
hydrothermal autoclave at 40 atm H2 for 12 h. After
finishing the reaction, the catalyst was filtered off; the
solvent was evaporated under reduced pressure. The
products 9 and 10 were separated and purificated by column
flash chromatography on silica gel using CH2Cl2 as eluent.
3-(1-Hydroxyethyl)isochroman-1-one (9).
ISSN 1814-9758. Ukr. Bioorg. Acta, 2024, Vol. 19, N 2
36
Yield: 658 mg, 34%; mp 48-50 °C (1:1 diastereomeric
mixture). 1H NMR (400 MHz, CDCl3) δ 8.04 (ddd, J = 7.8,
3.4, 1.4 Hz, 1H), 7.51 (tt, J = 7.6, 1.8 Hz, 1H), 7.35 (td, J =
7.6, 3.8 Hz, 1H), 7.24 (t, J = 6.9 Hz, 1H), 4.39 (dt, J = 12.5,
3.5 Hz, 0.5H), 4.33 (ddd, J = 12.5, 5.5, 3.0 Hz, 0.5H), 4.13
(qd, J = 6.5, 3.8 Hz, 0.5H), 3.96 (p, J = 6.4 Hz, 0.5H), 3.18
(dd, J = 16.4, 12.3 Hz, 0.5H), 3.11 (dd, J = 16.2, 12.6 Hz,
0.5H), 2.89 (dd, J = 16.4, 3.1 Hz, 0.5H), 2.83 (dd, J =
16.2 Hz, 3.1 Hz, 0.5H), 1.31 (d, J = 6.4 Hz, 1.5H), 1.29 (d,
J = 6.5 Hz, 1.5H). 13C NMR (100 MHz, CDCl3) δ 165.4 and
165.2, 139.2 and 138.9, 134.1 and 134.0, 130.4 and 130.3,
127.9 and 127.8, 127.7 and 127.7, 124.9 and 124.8, 82.5
and 82.2, 69.1 and 68.1, 29.6 and 27.2, 18.5 and 18.1.
HPLC (CI) m/z (M+H)+ 193.0.
3-Ethylisochroman-1-one (10).
Yield: 534 mg, 30%. Spectral and other data are in
agreement with Ref. [12], where compound 10 was
obtained by catalytic oxidation of 3-ethylisochroman.
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
[13]; a description of the technique is also given in [14].
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.
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Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на
ріст ракових клітин
О.В. Шабликін1, О.В. Шабликіна1,2*, І.Ю. Тарасюк2
1 Інститут біоорганічної хімії та нафтохімії ім. В.П. Кухаря НАН України, Київ, Україна
2 Київський національний університет імені Тараса Шевченка, Київ, Україна
Резюме: Застосовуючи різні умови, із 3-ацетил-1Н-ізохромен-1-ону отримано три продукти часткового відновлення: 3-(1-гідроксиетил)-
1H-ізохромен-1-он, 3-(1-гідроксиетил)ізохроман-1-он, 3-етилізохроман-1-он. Досліджена дія двох продуктів зі спиртовим фрагментом, а також
4-гідрокси-1,2,3,4-тетрагідро-6H-бензо[c]хромен-6-ону, на ріст ракових клітин шляхом однодозового випробування на 60 лініях ракових клітин.
Виявлено єдиний суттєвий вплив: 3-(1-гідроксиетил)-1H-ізохромен-1-он практично зупиняє ріст клітин лінії CCRF-CEM (Лейкемія).
Ключові слова: 3-ацетил-1Н-ізохромен-1-он (3-ацетилізокумарин); відновлення; ракові клітини.
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| language | English |
| last_indexed | 2026-07-20T01:01:31Z |
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| spelling | oai:ojs2.bioorganica.com.ua:article-882026-07-19T14:56:55Z Preliminary evaluation of the effect of partially hydrogenated 3-acetylisocoumarin derivatives on the cancer cells growth Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин Shablykin, Oleh V. Shablykina, Olga V. Tarasiuk, Ilona Yu. 3-acetyl-1H-isochromen-1-one (3-acetylisocoumarin) reduction cancer cells 3-ацетил-1Н-ізохромен-1-он (3-ацетилізокумарин) відновлення ракові клітини In different conditions, from 3-acetyl-1H-isochromen-1-one three partial reduction products were obtained, namely 3-(1-hydroxyethyl)-1H-isochromen-1-one, 3-(1-hydroxyethyl)isochroman-1-one, and 3-ethylisochroman-1-one. The influence of two products with an alcohol fragment, as well as 4-hydroxy-1,2,3,4-tetrahydro-6H-benzo[c]chromen-6-one, on the growth of cancer cells was investigated through One Doses Full NCI 60 Cell Panel Assay. The only one significant effect was found: 3-(1-hydroxyethyl)-1H-isochromen-1-one practically stops the growth of CCRF-CEM cell lines (Leukemia) Застосовуючи різні умови, із 3-ацетил-1Н-ізохромен-1-ону отримано три продукти часткового відновлення: 3-(1-гідроксиетил)-1H-ізохромен-1-он, 3-(1-гідроксиетил)ізохроман-1-он, 3-етилізохроман-1-он. Досліджена дія двох продуктів зі спиртовим фрагментом, а також 4-гідрокси-1,2,3,4-тетрагідро-6H-бензо[c]хромен-6-ону, на ріст ракових клітин шляхом однодозового випробування на 60 лініях ракових клітин. Виявлено єдиний суттєвий вплив: 3-(1-гідроксиетил)-1H-ізохромен-1-он практично зупиняє ріст клітин лінії CCRF-CEM (Лейкемія) 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/88 10.15407/bioorganica2024.02.033 Ukrainica Bioorganica Acta; Vol. 19 No. 2 (2024): Ukrainica Bioorganica Acta; 33-36 Ukrainica Bioorganica Acta; Том 19 № 2 (2024): Ukrainica Bioorganica Acta; 33-36 1814-9766 1814-9758 10.15407/bioorganica2024.02 en https://bioorganica.com.ua/index.php/journal/article/view/88/88 Copyright (c) 2024 Oleh V. Shablykin, Olga V. Shablykina, Ilona Yu. Tarasiuk https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | 3-ацетил-1Н-ізохромен-1-он (3-ацетилізокумарин) відновлення ракові клітини Shablykin, Oleh V. Shablykina, Olga V. Tarasiuk, Ilona Yu. Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин |
| title | Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин |
| title_alt | Preliminary evaluation of the effect of partially hydrogenated 3-acetylisocoumarin derivatives on the cancer cells growth |
| title_full | Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин |
| title_fullStr | Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин |
| title_full_unstemmed | Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин |
| title_short | Первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин |
| title_sort | первинна оцінка впливу частково гідрованих похідних 3-ацетилізокумарину на ріст ракових клітин |
| topic | 3-ацетил-1Н-ізохромен-1-он (3-ацетилізокумарин) відновлення ракові клітини |
| topic_facet | 3-acetyl-1H-isochromen-1-one (3-acetylisocoumarin) reduction cancer cells 3-ацетил-1Н-ізохромен-1-он (3-ацетилізокумарин) відновлення ракові клітини |
| url | https://bioorganica.com.ua/index.php/journal/article/view/88 |
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