Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом
A series of prenylated homoisoflavonoid-coumarin hybrids were synthesised by developed cascade reactions of coumarin Mannich bases with 3-(dimethylamino)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)prop-2-en-1-one. Obtained homoisoflavonoids might have a large potential for furth...
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V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
2022
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Ukrainica Bioorganica Acta| _version_ | 1871193565887987712 |
|---|---|
| author | Myshko, Nataliia V. Mrug, Galyna P. |
| author_facet | Myshko, Nataliia V. Mrug, Galyna P. |
| author_institution_txt_mv | [
{
"author": "Nataliia V. Myshko",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
},
{
"author": "Galyna P. Mrug",
"institution": "V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine"
}
] |
| author_sort | Myshko, Nataliia V. |
| baseUrl_str | https://bioorganica.com.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-19T14:56:53Z |
| description | A series of prenylated homoisoflavonoid-coumarin hybrids were synthesised by developed cascade reactions of coumarin Mannich bases with 3-(dimethylamino)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)prop-2-en-1-one. Obtained homoisoflavonoids might have a large potential for further investigations of their bioactivities |
| doi_str_mv | 10.15407/bioorganica2022.02.031 |
| first_indexed | 2025-07-17T12:19:36Z |
| format | Article |
| fulltext |
ISSN 1814-9758. Ukr. Bioorg. Acta, 2022, Vol. 17, N 2
UDC 547.814+547.728+547.772+547.94
DOI: hpps://doi.org/10.15407/bioorganica2022.02.031
31
RESEARCH ARTICLE
Synthesis of prenylated homoisoflavonoids with a coumarin moiety
Nataliia V. Myshko, Galyna P. Mrug*
V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine
Abstract: A series of prenylated homoisoflavonoid-coumarin hybrids were synthesized by developed cascade reactions of coumarin
Mannich bases with 3-(dimethylamino)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)prop-2-en-1-one. Obtained
homoisoflavonoids might have a large potential for further investigations of their bioactivities.
Keywords: coumarins; homoisoflavonoids; inverse electron-demand Diels-Alder reaction.
Introduction
The development of new synthetic routes for the
construction of natural product-like small-molecule libraries
with structural complexity, diversity, and various
physicochemical properties is attracting attention from the
scientific community involved in chemical biology and
drug discovery. The incorporation of privileged
substructural motifs a concept that there exist preferred
molecular scaffolds that can provide ligands for diverse
receptors has been proven to be an essential tool for the
discovery of bioactive molecules [1]. The naturally
occurring homoisoflavonoids possess a broad spectrum of
biological activities, such as antioxidant, anti-microbial,
anti-diabetic, immunomodulatory effects, and protein
kinase inhibition [2-4].
The sappanin-type homoisoflavonoids contain chromanone
or chromone rings with 3-benzyl substituents. Like other
flavonoid counterparts, naturally occurring homoiso-
flavonoids typically bear hydroxylic, methoxy, and
methylenedioxy groups in rings A and B. Isoprenyl and
geranyl moieties, methyl groups, and aldehydes have been
described as C-linked substituents [5].
Received:
Revised:
Accepted:
Published online:
06.10.2022
20.10.2022
27.10.2022
30.12.2022
Corresponding author. Tel.: +380-44-558-5388;
e-mail: galja.mrug@ukr.net (G.P. Mrug)
ORCID: 0000-0002-0370-0630
Isolated from the bulbs of Ledebouria Floribunda
prenylated and geranylated flavonoids are very common in
certain families of plants. The first examples of prenylated
homoisoflavonoids are ledebourin A, B, and C 1a-1c
(Figure 1). These derivatives are the products of triple
(acetate, shikimate, and mevalonate) biosynthetic pathways
and have been reported as potent antioxidants. The expected
activity due to the ortho-dihydroxy groups is probably
enhanced by other factors introduced by the prenyl and
geranyl groups [6].
Results and discussion
It should be noted that a few types of C-prenylated
flavonoids have been isolated from natural sources. In most
cases, naturally occurring flavonoids contain 2H-2,2-
dimethylchromene or isopropylbenzofuran fragment, and
ring-opening isoprenyl substituent which can be
transformed to hydroxy or epoxy derivatives etc.
Intramolecular cyclization of ortho-hydroxyprenylated
flavonoids affords rarely isolated 2,2-dimethylchromane
derivatives, which usually undergo oxidation to 2H-2,2-
dimethylchromene derivatives. For example, a few
C-isoprenyl flavonoids 2 [7, 8] as well as their cyclic
isomers 3 [7, 9] were isolated from Epimedium diphilum,
Bursera leptophloes (Figure 1).
Direct prenylation of phenols is a challenging problem for
the synthesis of prenylated flavonoids. In the case of
coumarins and chromones, direct prenylation was achieved
using prenyl- or geranyl halides [10-14], 2-methyl-3-
butene-2-ol [15], and enzyme-catalyzed prenylation with
dimethylallyl diphosphate or geranyl diphosphate [16-18].
© Myshko N.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
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ISSN 1814-9758. Ukr. Bioorg. Acta, 2022, Vol. 17, N 2
32
O O
OH O
OMe
HO
O
OH O
OMe
R
O
OH
OH O
HO
OH
O
OH
OH O
HO
OMe
O
OH
O
OH
OH
O
OH
O
OMe
OH
O
OH
O
OH
O
O O O
O
OH
O O
HO
OH
1a ledebourin A 1b ledebourin B (R = H)
1c ledebourin C (R = isoprenyl)
2a 2b 2c
3a 3b 3c
Figure 1. Chemical structures of some prenylated sappanin-type natural homoisoflavonoids and ring-chain isomeric prenylated flavones.
O OH
OOMe
DMF-DMA
neat
O OH
OOMe
NMe2
O
NMe2
HO O
R
5a-5e O
OMe
O HO
O
O
R
O
6a-6e3 4
Scheme 1. Synthesis of homoisoflavonoid-coumarin hybrids.
However, in a similar condition, the formation of
isoprenyl-substituted compounds and/or 2,2-dimethyl-
chromanes was observed. It should be noted, these reactions
had poor selectivity and yield; the formation of
O-prenylated, 6,6- or 8,8-bisprenylated compounds was
observed using 5,7-dihydroxycoumarins [11, 19] and
5,7-dihydroxychromones [20]; C-3 prenylation of
coumarins also was observed [10].
Moreover, this reaction is impossible in the case of A-
and B- ring flavonoids due to the low selectivity of
prenylation. For the synthesis of A-ring prenylated
homoisoflavonoids-coumarin hybrids, we used described
one-pot procedure which includes inverse electron-demand
Diels-Alder reaction with subsequent intramolecular
cascade reactions (Scheme 1) [21].
Started enaminone 4 was synthesized by a reaction of
1-(5-hydroxy-7-methoxy-2,2-dimethylchroman-6-yl)ethan-
1-one (3) with dimethylformamide dimethyl acetal.
8-Dimethylaminomethyl-7-hydroxycoumarins were synthe-
sized by aminomethylation of 7-hydroxycoumarins with
bis(dimethylamino)methane in propanol-2 solution.
The reaction of enaminone 4 with coumarin Mannich
bases 5a-5e was carried out in DMF at reflux for 6 h. The
formation of compounds 6a-6e could be considered as
cascade reactions which include: the thermally generated
formation of quinone methides 7 from coumarin Mannich
bases 5, inverse electron-demand Diels-Alder reaction of
compounds 7 with enaminone 4, deamination of hemi-
aminals 8 with the formation of 4H-chromeno derivatives 9,
and intramolecular nucleophilic attack of C-4 with the
N.V. Myshko, G.P. Mrug
33
phenolic group. As result, compounds 6a-6e were alone
products of the reaction of enaminone 4 with 8-dimethyl-
aminomethylcoumarins 5a-5e (Scheme 2).
Conclusions
As a result, we demonstrated the efficient synthesis of
3-(7-hydroxy-2-oxo-2H-chromen-8-ylmethyl)-5-methoxy-
8,8-dimethyl-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-4-
ones as isomers of prenylated homoisoflavonoid-coumarin
hybrids by the cascade reaction of (2E)-3-(dimethylamino)-
1-(5-hydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-
chromen-6-yl)prop-2-en-1-one with 7-hydroxycoumarin
Mannich bases.
Experimental section
1H and 13C spectra were recorded on Bruker 500
(500/125 MHz) or Bruker 400 (400/100 MHz)
spectrometers in CDCl3 [residual CHCl3 (δH = 7.26 ppm) or
CDCl3 (δC = 77.16 ppm) as internal standard] or DMSO-d6
[residual SO(CD3)(CD2H) (δH = 2.50 ppm) or SO(CD3)2
(δC = 39.52 ppm) as internal standard]. Melting points were
determined in open capillary tubes using Buchi B-535
apparatus and were uncorrected. Mass spectra were
obtained using an Agilent 1100 spectrometer using APCI
(atmospheric-pressure chemical ionization). Elemental
analysis was performed on a Vario MICRO сube automated
CHNS-analyzer. Column chromatography was performed
using Macherey-Nagel Silica 60, 0.04-0.063 mm silica gel.
Compound 5a was synthesized as reported previously
[21].
(2E)-3-(Dimethylamino)-1-(5-hydroxy-7-methoxy-2,2-
di-methyl-3,4-dihydro-2H-chromen-6-yl)prop-2-en-1-one
(4).
A mixture of 0.75 g (3 mmol) in 2 ml DMF-DMA was
heated at reflux for 1 h, cooled, and formed residue was
filtered off and washed with MeOH. Compound 4 was
recrystallized from MeOH.
Yield 513 mg, 56%; mp 187-189 °C. 1H NMR (400
MHz, CDCl3) δ 15.98 (s, 1H), 7.88 (d, J 12.4 Hz, 1H), 6.26
(d, J 12.4 Hz, 1H), 5.82 (s, 1H), 3.79 (s, 3H), 3.09 (s, 3H),
2.91 (s, 3H), 2.60 (d, J 6.7 Hz, 2H), 1.77 (t, J 6.7 Hz, 2H),
1.32 (s, 6H). 13C NMR (125 MHz, CDCl3) δ 190.2, 165.1,
159.9, 158.4, 154.0, 104.5, 102.0, 97.0, 91.1, 75.4, 55.5,
45.1, 37.3, 32.4, 26.8, 16.4. LC/MS (APCI) m/z 306.2
[M+H]+. Anal. calcld. for C17H23NO4: C, 66.86; H, 7.59;
N, 4.59. Found: C, 66.71; H, 7.48; N, 4.81.
General procedure for the synthesis of 8-dimethy-
laminomethylcoumarins 5.
To a stirred suspension of coumarins 5c-5e (2 mmol) in
10 mL of isopropanol was added 0.3 mL (2.2 mmol, 1.1 eq)
of bis(N,N-dimethylamino)methane at 70 °C. The mixture
was heated at 80 °C for 2 h and cooled, and diluted with
hexane. The formed residue was filtered off and washed
with hexane. The Mannich bases 5 were recrystallized from
isopropanol-hexane.
8-[(Dimethylamino)methyl]-7-hydroxy-4-methyl-2H-
chromen-2-one (5b).
Yield 271 mg, 58%; mp 95-97 °C. 1H NMR (400 MHz,
CDCl3) δ 12.55 (s, 1H), 7.33 (d, J 8.7 Hz, 1H), 6.68 (d, J
8.7 Hz, 1H), 5.98 (s, 1H), 3.92 (s, 2H), 2.33 (s, 6H), 2.31 (s,
3H). 13C NMR (125 MHz, CDCl3) δ 162.9, 161.1, 153.3,
O
5a-5e
O
8a-8e
HO
NMe2
O
R
OO O
R
7a-7e
O
OMe
OH
NMe2
O
4
O
O
OH
O O
R
Me2N
MeO
O
OMe
O
O
R
O
OH
O
9a-9e
O
OMe O
R
O
O
6a-6e
O HO
Scheme 2. Plausible reaction mechanism.
ISSN 1814-9758. Ukr. Bioorg. Acta, 2022, Vol. 17, N 2
34
152.3, 124.6, 113.3, 112.0, 110.4, 108.0, 55.1, 44.4, 18.
LC/MS (APCI) m/z 234.2 [M+H]+. Anal. calcld. for
C13H15NO3: C, 66.94; H, 6.48; N, 6.00. Found: C, 67.31;
H, 6.71; N, 6.25.
8-[(Dimethylamino)methyl]-7-hydroxy-4-(methoxyme-
thyl)-2H-chromen-2-one (5c).
Yield 448 mg, 85%; mp 126-128 °C. 1H NMR (500
MHz, CDCl3) δ 11.20 (s, 1H), 7.33 (d, J 8.7 Hz, 1H), 6.73
(d, J 8.7 Hz, 1H), 6.30 (s, 1H), 4.56 (s, 2H), 4.00 (s, 2H),
3.48 (s, 3H), 2.38 (s, 6H). 13C NMR (100 MHz, CDCl3) δ
163.0, 161.3, 152.6, 152.3, 123.8, 113.5, 109.6, 108.5,
108.3, 70.4, 59.1, 55.2, 44.5. LC/MS (APCI) m/z 264.0
[M+H]+. Anal. calcld. for C14H17NO4: C, 63.87; H, 6.51;
N, 5.32. Found: C, 64.13; H, 6.26; N, 5.44.
8-[(Dimethylamino)methyl]-7-hydroxy-4-isopropyl-2H-
chromen-2-one (5d).
Yield 392 mg, 75%; mp 130-132 °C. 1H NMR (400
MHz, CDCl3) δ 11.40 (s, 1H), 7.41 (d, J 8.9 Hz, 1H), 6.68
(d, J 8.8 Hz, 1H), 6.02 (s, 1H), 3.93 (s, 2H), 3.17 (hept, J
6.8 Hz, 1H), 2.32 (s, 6H), 1.21 (d, J 6.8 Hz, 6H). 13C NMR
(100 MHz, CDCl3) δ 163.0, 162.6, 161.9, 152.6, 124.1,
113.3, 110.7, 108.3, 106.4, 55.2, 44.4, 28.5, 21.9. LC/MS
(APCI) m/z 262.2 [M+H]+. Anal. calcld. for C15H19NO3:
C, 68.94; H, 7.33; N, 5.36. Found: C, 68.77; H, 7.52; N,
5.21.
4-Cyclopropyl-8-[(dimethylamino)methyl]-7-hydroxy-
2H-chromen-2-one (5e).
Yield 482 mg, 93%; mp 136-138 °C. 1H NMR (400
MHz, CDCl3) δ 12.57 (s, 1H), 7.67 (d, J 8.8 Hz, 1H), 6.72
(d, J 8.8 Hz, 1H), 5.75 (s, 1H), 3.94 (s, 2H), 2.34 (s, 6H),
2.11-1.88 (m, 1H), 1.16-0.97 (m, 2H), 0.87-0.62 (m, 2H).
13C NMR (125 MHz, CDCl3) δ 162.9, 161.9, 158.7, 152.2,
124.7, 113.3, 112.3, 108.0, 105.4, 55.2, 44.5, 12.0, 8.1.
LC/MS (APCI) m/z 260.2 [M+H]+. Anal. calcld. for
C15H17NO3: C, 69.48; H, 6.61; N, 5.40. Found: C, 69.73;
H, 6.45; N, 5.67.
General procedure for the synthesis of homo-
isoflavonoids 6.
A mixture of enaminone 4 (1 mmol) and corresponding
Mannich base 5a-e (1 mmol) in DMF (10 mL) was stirred
at reflux for 6 h. The reaction mixture was cooled, the
solvent was evaporated, and formed residue was washed
with water and purified by recrystallization from DMF-
MeOH mixture.
3-[(7-Hydroxy-2-oxo-2H-chromen-8-yl)methyl]-5-me-
thoxy-8,8-dimethyl-9,10-dihydro-4H,8H-pyrano[2,3-f]-
chromen-4-one (6a).
Yield 326 mg, 75%; mp 263-265 °C. 1H NMR (400
MHz, DMSO-d6) δ 10.67 (s, 1H), 7.92 (d, J 9.4 Hz, 1H),
7.53 (s, 1H), 7.44 (d, J 8.5 Hz, 1H), 6.87 (d, J 8.5 Hz, 1H),
6.32 (s, 1H), 6.20 (d, J 9.4 Hz, 1H), 3.77 (s, 3H), 3.70 (s,
2H), 2.58 (t, J 6.7 Hz, 2H), 1.75 (t, J 6.7 Hz, 2H), 1.27 (s,
6H). 13C NMR (125 MHz, DMSO-d6) δ 175.6, 160.4, 159.2,
158.4, 157.9, 156.4, 153.6, 150.4, 144.8, 127.7, 122.0,
112.9, 111.6, 111.5, 111.2, 107.5, 100.8, 96.8, 75.9, 55.9,
31.0, 26.2, 18.8, 15.7. LC/MS (APCI) m/z 435.2 [M-H]-.
Anal. calcld. for C25H22O7: C, 69.12; H, 5.10. Found:
C, 69.03; H, 5.38.
3-[(7-Hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)meth-
yl]-5-methoxy-8,8-dimethyl-9,10-dihydro-4H,8H-pyrano-
[2,3-f]chromen-4-one (6b).
Yield 309 mg, 69%; mp 268-270 °C. 1H NMR (400
MHz, DMSO-d6) δ 10.62 (s, 1H), 7.56-7.48 (m, 2H), 6.88
(d, J 8.8 Hz, 1H), 6.31 (s, 1H), 6.12 (s, 1H), 3.77 (s, 3H),
3.70 (s, 2H), 2.58 (t, J 6.6 Hz, 2H), 2.35 (s, 3H), 1.75 (d, J
6.6 Hz, 2H), 1.27 (s, 6H). 13C NMR (125 MHz, DMSO-d6)
δ 175.6, 160.2, 159.0, 158.4, 157.9, 156.4, 153.7, 152.9,
150.3, 124.4, 122.1, 112.6, 112.3, 111.5, 110.1, 107.5,
100.8, 96.8, 75.9, 55.9, 31.0, 26.2, 18.9, 18.2, 15.7. LC/MS
(APCI) m/z 449.0 [M+H]+. Anal. calcld. for C26H24O7:
C, 69.63; H, 5.39. Found: C, 69.84; H, 5.53.
3-{[7-Hydroxy-4-(methoxymethyl)-2-oxo-2H-chromen-8-
yl]methyl}-5-methoxy-8,8-dimethyl-9,10-dihydro-4H,8H-
pyrano[2,3-f]chromen-4-one (6c).
Yield 388 mg, 81%; mp 261-263 °C. 1H NMR (400
MHz, DMSO-d6) δ 10.66 (s, 1H), 7.54 (s, 1H), 7.46 (d, J
8.7 Hz, 1H), 6.87 (d, J 8.7 Hz, 1H), 6.33 (s, 1H), 6.19 (s,
1H), 4.62 (s, 2H), 3.77 (s, 3H), 3.71 (s, 2H), 3.41 (s, 3H),
2.60 (t, J 6.7 Hz, 2H), 1.76 (t, J 6.7 Hz, 2H), 1.28 (s, 6H).
13C NMR (125 MHz, DMSO-d6) δ 175.6, 160.3, 159.0,
158.4, 157.9, 156.4, 153.1, 152.8, 150.4, 123.7, 122.0,
112.7, 111.7, 109.9, 107.8, 107.5, 100.9, 96.9, 76.0, 69.5,
58.4, 55.9, 31.0, 26.2, 19.0, 15.7. LC/MS (APCI) m/z 479.0
[M+H]+. Anal. calcld. for C27H26O8: C, 67.77; H, 5.48.
Found: C, 67.53; H, 5.65.
3-[(7-Hydroxy-4-isopropyl-2-oxo-2H-chromen-8-yl)-me-
thyl]-5-methoxy-8,8-dimethyl-9,10-dihydro-4H,8H-pyrano-
[2,3-f]chromen-4-one (6d).
Yield 372 mg, 78%; mp 246-248 °C. 1H NMR (400
MHz, DMSO-d6) δ 10.61 (s, 1H), 7.64 (d, J 7.2 Hz, 1H),
7.55 (s, 1H), 6.90 (d, J 8.7 Hz, 1H), 6.34 (s, 1H), 6.09 (s,
1H), 3.78 (s, 3H), 3.71 (s, 2H), 3.34 3.26 (m, 1H), 2.61 (d, J
6.6 Hz, 1H), 1.77 (d, J 6.6 Hz, 3H), 1.28 (s, 6H), 1.23 (d, J
6.7 Hz, 6H). 13C NMR (125 MHz, DMSO-d6) δ 175.6,
162.9, 160.7, 158.8, 158.4, 158.0, 156.4, 153.2, 150.4,
123.9, 122.1, 112.8, 111.9, 111.0, 107.5, 106.3, 100.8, 96.9,
75.9, 55.9, 31.0, 28.0, 26.2, 21.7, 19.0, 15.7. LC/MS
(APCI) m/z 477.0 [M+H]+. Anal. calcld. for C28H28O7:
C, 70.58; H, 5.92. Found: C, 70.36; H, 6.17.
3-[(4-Cyclopropyl-7-hydroxy-2-oxo-2H-chromen-8-yl)-
methyl]-5-methoxy-8,8-dimethyl-9,10-dihydro-4H,8H-py-
rano[2,3-f]chromen-4-one (6e).
Yield 266 mg, 56%; mp 244-246 °C. 1H NMR (400
MHz, DMSO-d6) δ 10.64 (s, 1H), 7.81 (d, J 8.8 Hz, 1H),
7.53 (s, 1H), 6.91 (d, J 8.8 Hz, 1H), 6.31 (s, 1H), 5.81 (s,
1H), 3.77 (s, 3H), 3.71 (s, 2H), 2.56 (t, J 6.6 Hz, 2H), 2.27-
2.12 (m, 1H), 1.73 (d, J 6.6 Hz, 2H), 1.25 (s, 6H), 1.13-1.00
(m, 2H), 0.91-0.77 (m, 2H). 13C NMR (125 MHz, DMSO-
d6) δ 175.6, 160.7, 159.0, 158.9, 158.4, 157.9, 156.4, 152.8,
150.4, 124.3, 122.1, 112.7, 112.5, 111.6, 107.5, 104.5,
N.V. Myshko, G.P. Mrug
35
100.8, 96.8, 75.9, 55.9, 31.0, 26.2, 19.0, 15.7, 11.5, 8.6.
LC/MS (APCI) m/z 475.0 [M+H]+. Anal. calcld. for
C28H26O7: C, 70.87; H, 5.52. Found: C, 70.63; H, 5.76.
Notes
The authors declare no conflict of interest.
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Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом
Н.В. Мишко*, Г.П. Мруг
Інститут біоорганічної хімії та нафтохімії ім. В.П. Кухаря НАН України, Київ, Україна
Резюме: Cинтезовано ряд пренільованих гомоізофлавоноїд-кумаринових гібридів шляхом каскадних реакцій кумаринових основ Манніха з
3-(диметиламіно)-1-(5-гідрокси-7-метокси-2,2-диметил-3,4-дигідро-2Н-хромен-6-іл)проп-2-ен-1-оном. Отримані гомоїзофлавоноїди можуть мати
великий потенціал для подальших досліджень їх біологічної активності.
Ключові слова: кумарини; гомоізофлавоноїди; обернена за електронними вимогами реакція Дільса-Альдера.
Notes
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| id | oai:ojs2.bioorganica.com.ua:article-33 |
| institution | Ukrainica Bioorganica Acta |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-20T01:00:44Z |
| publishDate | 2022 |
| 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/c1/5688c29728408557c49f923c4d7fa6c1.pdf |
| spelling | oai:ojs2.bioorganica.com.ua:article-332026-07-19T14:56:53Z Synthesis of prenylated homoisoflavonoids with a coumarin moiety Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом Myshko, Nataliia V. Mrug, Galyna P. сumarins homoisoflavonoids inverse electron-demand Diels-Alder reaction кумарини гомоізофлавоноїди обернена за електронними вимогами реакція Дільса-Альдера A series of prenylated homoisoflavonoid-coumarin hybrids were synthesised by developed cascade reactions of coumarin Mannich bases with 3-(dimethylamino)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)prop-2-en-1-one. Obtained homoisoflavonoids might have a large potential for further investigations of their bioactivities Cинтезовано ряд пренільованих гомоізофлавоноїд-кумаринових гібридів шляхом каскадних реакцій кумаринових основ Манніха з 3-(диметиламіно)-1-(5-гідрокси-7-метокси-2,2-диметил-3,4-дигідро-2Н-хромен-6-іл)проп-2-ен-1-оном. Отримані гомоїзофлавоноїди можуть мати великий потенціал для подальших досліджень їх біологічної активності. V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine 2022-12-30 Article Article application/pdf https://bioorganica.com.ua/index.php/journal/article/view/33 10.15407/bioorganica2022.02.031 Ukrainica Bioorganica Acta; Vol. 17 No. 2 (2022): Ukrainica Bioorganica Acta; 31-35 Ukrainica Bioorganica Acta; Том 17 № 2 (2022): Ukrainica Bioorganica Acta; 31-35 1814-9766 1814-9758 10.15407/bioorganica2022.02 en https://bioorganica.com.ua/index.php/journal/article/view/33/51 Copyright (c) 2022 Nataliia V. Myshko, Galyna P. Mrug https://creativecommons.org/licenses/by/4.0 |
| spellingShingle | кумарини гомоізофлавоноїди обернена за електронними вимогами реакція Дільса-Альдера Myshko, Nataliia V. Mrug, Galyna P. Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом |
| title | Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом |
| title_alt | Synthesis of prenylated homoisoflavonoids with a coumarin moiety |
| title_full | Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом |
| title_fullStr | Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом |
| title_full_unstemmed | Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом |
| title_short | Синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом |
| title_sort | синтез пренільованих гомоізофлавоноїдів із кумариновим фрагментом |
| topic | кумарини гомоізофлавоноїди обернена за електронними вимогами реакція Дільса-Альдера |
| topic_facet | сumarins homoisoflavonoids inverse electron-demand Diels-Alder reaction кумарини гомоізофлавоноїди обернена за електронними вимогами реакція Дільса-Альдера |
| url | https://bioorganica.com.ua/index.php/journal/article/view/33 |
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