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Abstracts ICPS 2023

1,2
, D.A. Narbutaeva
1
, A.M. Karakulova
1
,
F.M. Tursunkhodzhaeva
1
, V.I. Vinogradova
1
 
 
1) S.Yu. Yunusov Institute of the Chemistry of Plant Substances Academy of sciences of 
the Republic of Uzbekistan st. Mirzo-Ulugbek, 77, 100170 Tashkent 
 
e-mail: j.sherzod.78@mail.ru 
2) National University of Uzbekistan named after Mirzo Ulugbek, 
Universitetskaya st., 4, 100174 Tashkent, Uzbekistan 
Plant flavonoids have antibacterial, anti-inflammatory, anticancer, capillary-
stabilizing properties associated with antioxidant, membrane-stabilizing effects, and 
other properties, which makes them quite valuable synthons for chemical modifications, 
biological activity studies, and development of new drugs.
The best known and available flavonoids are quercetin (QV, 
1
) and dihydroquercetin 
(DHQ). Continuing our work on the synthesis of bimolecular compounds containing 
fragments of flavonoids and isoquinolines, it was studied the Mannich reaction QV (
1

involving formaldehyde and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines of various 
structures. 
The interaction of quercetin (QV) with 1-aryl-(or H)-6,7-dimethoxy-1,2,3,4-
tetrahydroisoquinolines 
by 
the 
Mannich 
reaction 
synthesized 
heterocyclic 
monosubstituted conjugates of QV in 75-96% yield. It should be noted that, in contrast 
to a similar reaction with dihydroquercetin, that use of quercetin-isoquinoline-
formaldehyde in a ratio of 1:2:2 leads to the reaction progress only at the position 8.
Scheme. 
Reaction of QV with 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines
 2 a-k. 
The structure of the obtained substances was proved on the basis of IR, mass, 
1
Н and 
13
С NMR spectra.
Among the synthesized conjugates, compounds 
3d–3g
were found much more 
effective in hypoxia and antioxidant than the initial substances, including quercetin, which 
indicates the prospects for further obtaining such conjugates and studying their biological 
properties. 
O
O
OH
OH
OH
HO
OH
CH
2
O

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