Synthesis of Betulin Dibenzoate and Diphthalate

Published on Mar 1, 2017in Chemistry of Natural Compounds0.809
· DOI :10.1007/S10600-017-1976-5
V. A. Levdanskii4
Estimated H-index: 4
(SibFU: Siberian Federal University),
A. V. Levdanskii3
Estimated H-index: 3
(RAS: Russian Academy of Sciences),
Boris N. Kuznetsov22
Estimated H-index: 22
(SibFU: Siberian Federal University)
Source
Abstract
Betulin-3,28-dibenzoate and -3,28-diphthalate were synthesized for the first time by reacting betulin with melts of benzoic and phthalic acids at 190–200°C for 5 min.
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References4
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#1K.-T. ChueH-Index: 2
#2M.-S. ChangH-Index: 1
Last. L. N. TenH-Index: 1
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Betulin isonicotinate, 6-chloronicotinate, 2-chlorocinnamate, and benzoates were synthesized by the reaction of betulin and the acid chlorides. It was shown that the 3,4-difluorobenzoate exhibited antibacterial activity against Ochrobactrum anthropi, Stenotrophomonas maltophilia, and S. nitritireducens whereas the 3,5-dinitrobenzoate was active against the last two microorganisms.
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#1O. B. Flekhter (RAS: Russian Academy of Sciences)H-Index: 15
#2Natalya I. Medvedeva (RAS: Russian Academy of Sciences)H-Index: 10
Last. Tolstikov Genrikh A (RAS: Russian Academy of Sciences)H-Index: 29
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A series of new triterpene hemisuccinates, hemiphthalates and nicotinates have been obtained with 52 – 95% yields via reactions of monoacetates of betulin, betulinic acid, and allobetulin with succinic and phthalic anhydrides and with nicotinic acid chloroanhydride. 3-O-Acetylbetulin-28-O-hemiphthalate showed the most pronounced antiinflammatory activity comparable with the effect of ortophen (diclofenac). 3-O-Acetylbetulin-28-O-hemisuccinate exhibited the most pronounced antiulcer activity comp...
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#1Miroslav Kvasnica (Charles University in Prague)H-Index: 15
#2Jan Sarek (Charles University in Prague)H-Index: 14
Last. Hajdúch M (Palacký University, Olomouc)H-Index: 19
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Synthesis of 3β-O-phthalic esters from betulinic acid and its esters and synthesis of phthalic esters from betulin and its monoacetates using classical acylation procedure with phthalic anhydride. The evaluation of cytotoxicity of the prepared compounds was using numbers of tumor cell lines in MTT test. It was discovered that hemiphthalic esters had better cytotoxicity than starting compounds as betulinic acid or quite inactive betulin.
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#1O. B. Flekhter (RAS: Russian Academy of Sciences)H-Index: 15
#2L. T. Karachurina (RAS: Russian Academy of Sciences)H-Index: 8
Last. Tolstikov Genrikh A (RAS: Russian Academy of Sciences)H-Index: 29
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Hemisuccinates, hemiphthalates, acetylsalicylates, cinnamates, andp-methoxycinnamates of lupeol, betulin, and 3-O-acetylbetulin were synthesized via interaction with corresponding acid anhydrides or acid chlorides. A number of betulin esters in position 3 and 28 were shown to exhibit a pronounced hepatoprotective effect similar to that of betulin and silibor. These experimental data were in a good agreement with the computer prediction of their biological activity. Betulin 3,28-bishemiphthalate ...
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#1V. A. Vydrina (RAS: Russian Academy of Sciences)H-Index: 6
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A new synthesis of 3-oxo-28-hydroxylup-20(29)-ene from the available natural triterpenoid betulin was developed. α,ω-Diketodiesters were prepared for the first time by different methods from 3-oxo-28-hydroxylup-20(29)-ene and a series of natural dicarboxylic acids. Steglich reaction conditions gave the highest yields. One of the synthesized α,ω-diketodiesters was moderately active in vitro against A-549 lung carcinoma.
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The complexation of ester betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD) was studied by mobility shift affinity CE. Electrophoretic mobility for triangular peaks was calculated using the parameter a1 of the Haarhoff-Van der Linde function instead of the peak top time. Dependences of the viscosity corrected electrophoretic mobility on HP-β-CD concentration were not described on the basis of only complexes with 1:1 stoichiometry due to the fact that these binding curves did no...
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#1V. A. Levdansky (RAS: Russian Academy of Sciences)H-Index: 2
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Complexation plays an important role in many biological phenomena, the analysis of different samples, optimization of separation processes, and increasing the pharmacological activity of drugs. This paper discusses the features of using mobility shift affinity capillary electrophoresis for studying strong complexation. Electrophoretic peaks for this case are often triangular. It was shown that the use of electrophoretic mobility obtained from the peak apex time to calculate binding constants lea...
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Ozonolysis of 3β,28-diacyloxylup-20,29-enes gave 20-oxo-29-nor-3β,28-diacyloxylup-20,29-enes, which were brominated with molecular bromine in AcOH to obtain a mixture of 30-bromo- and 30-dibromo derivatives. Ozonolysis of 30-bromo-3β,28-diacylbetulin produced 29-nor-30-bromoketones, whose reaction with sodium azide afforded 29-nor-30-azidoketones of the lupane series.
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#1A. V. Levdanskii (RAS: Russian Academy of Sciences)H-Index: 3
#2Alexander A. Kondrasenko (RAS: Russian Academy of Sciences)H-Index: 5
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