V. A. Vydrina
Russian Academy of Sciences
TriterpenoidBiological activityMedicinal chemistryOrganic chemistryInorganic chemistryChemistryHydroborationTerpenoidWittig reactionAdipic acidMoietyPheromoneMethyleneMonoterpeneHydrideDiboranePerformic acidBetulinChlorideMenthoneLactolRicinoleic acidAldehydeDiisobutylaluminum hydrideInsect pheromonesOptically activeReagentSex pheromoneStereochemistryBiologyZoologyReduction (complexity)
43Publications
5H-index
62Citations
Publications 42
Newest
#1V. A. Vydrina (RAS: Russian Academy of Sciences)H-Index: 5
#2R. R. Sayakhov (RAS: Russian Academy of Sciences)H-Index: 1
Last. G. Yu. Ishmuratov (RAS: Russian Academy of Sciences)H-Index: 11
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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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Efficient methods have been developed for the synthesis of three potentially useful macroheterocycles containing pyridine-2,6-dicarboxylic and adipic acid ester and hydrazide fragments starting from tetrahydropyran (commercial petrochemical product) through intermediate 8-hydroxyoctan-2-one. The key stages were [2+1]-condensation of the latter with pyridine-2,6-dicarboxylic and adipic acid chlorides and [1+1]-condensation of the resulting α,ω-diketo diesters with dihydrazides derived from the sa...
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#1Mikhail V. DubininH-Index: 10
#2Alena A. SemenovaH-Index: 2
Last. Konstantin N. Belosludtsev (RAS: Russian Academy of Sciences)H-Index: 14
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Abstract The paper considers the effects of plant triterpenoid betulin and its derivative betulonic acid on rat liver mitochondria and liposomes. It was found that betulonic acid and, to a lesser extent, betulin, activate mitochondrial respiration in states 2 and 4 and inhibit ADP- and DNP-stimulated (uncoupled) respiration. The effect of betulonic acid resulted in a significant decrease of the respiratory control and ADP/O ratios and decrease in Δψ. The effects of both compounds were most prono...
9 CitationsSource
#1N. M. IshmuratovaH-Index: 5
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#1Marina P. Yakovleva (RAS: Russian Academy of Sciences)H-Index: 9
#2V. A. Vydrina (RAS: Russian Academy of Sciences)H-Index: 5
Last. G. Yu. Ishmuratov (RAS: Russian Academy of Sciences)H-Index: 11
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We earlier discovered a new reaction in the chemistry of organoaluminum compounds (OACs), specifically, the formation of O-isobutyl acetals on low-temperature (–70°C) treatment of seven-membered lactones with a double (or more) molar amount of diisobutylaluminum hydride (DIBAH) in methylene chloride. To assess the boundaries for the formation of isobutyl acetals depending on the ring size, we involved in the low-temperature hydride reduction six-, eight-, and thirteen-membered lactones. To deter...
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#1V. A. VydrinaH-Index: 5
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Реакция гидроборирования-окисления широко используется в химии терпеноидов как для доказательства структуры выделенных из природного сырья новых соединений, так и в направленном синтезе низкомолекулярных биорегуляторов. Причем большая часть известных примеров затрагивает моно- и сесквитерпены, гораздо меньшее количество – для ди- и тритерпеноидов: большинство представлено гидроборированием-окислением локализованных двойных связей, примеры для сопряженных диенов ограничены лишь гидроборированием-...
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An effective reagent (performic acid) was proposed for the Bayer–Villiger oxidation of glycyrrhetic acid methyl ester to the corresponding oxepan-2-one. The low-temperature (–70°C) reduction of the latter with excess (5 equiv) diisobutylaluminium hydride in CH2Cl2 resulted in the isolation of 3,4-seco-18β-oleane-4(23),9(11),12-triene-3,30-diol as the main product, while the expected (R)-3,4-epoxy-3-isobutoxy-3,4-seco-18β-oleane-11,12-dien-30-ol was the minor product.
1 CitationsSource
#1N. M. IshmuratovaH-Index: 5
Last. G. Yu. IshmuratovH-Index: 11
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#1Marina P. Yakovleva (RAS: Russian Academy of Sciences)H-Index: 9
#2V. A. Vydrina (RAS: Russian Academy of Sciences)H-Index: 5
Last. G. Yu. Ishmuratov (RAS: Russian Academy of Sciences)H-Index: 11
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Examples of hydroboration–oxidation of natural mono-, sesqui-, di-, and triterpenoids are reviewed. Diborane, BH3·THF, BH3·Me2S, disiamylborane, thexylborane, dicyclohexylborane, 9-borabicyclo[3,3,1]nonane (9-BBN), and diisopinocampheylborane are used as the hydroboration reagents; H2O2 mixed with KOH, NaOH, and NaOAc, as the oxidants. Most of the examples address mono- and sesquiterpenoids with far fewer describing di- and triterpenoids.
2 CitationsSource