Regioselective Transformation of the Cyano Group of Triterpene α,β-Alkenenitriles

Konysheva, A. V.; Толмачева, И. А.; Savinova, Olga V.; Бореко, Е. И.; Гришко, В. В.

doi:10.1007/s10600-017-2091-3

Cited by 5 publications

(2 citation statements)

References 15 publications

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“…To continue a search for agents active against herpes simplex virus, unsaturated acids, including difficultly accessible ceanothane-type ones, were prepared by the same authors, using alkaline hydrolysis of semi-synthetic triterpenoids with 1-cyano- or 3-methyl-1-cyanoalkene fragments in five-membered ring A (Scheme 11) [69]. Regioselective reduction of 1-cyano-19β,28-epoxy-2-nor-18α H -olean-1(3)-ene by DIBAL-H resulted in a synthesis of 2-aminomethyl-19β,28-epoxy-2-nor-18α H -olean-1(3)-ene.…”

Section: Derivatives Of Betulinic Acid Their Pharmacological Effementioning

confidence: 99%

Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

2019

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The subject of this review article refers to the recent achievements in the investigation of pharmacological activity and supramolecular characteristics of betulinic acid and its diverse derivatives, with special focus on their cytotoxic effect, antitumor activity, and antiviral effect, and mostly covers a period 2015–2018. Literature sources published earlier are referred to in required coherences or from historical points of view. Relationships between pharmacological activity and supramolecular characteristics are included if such investigation has been done in the original literature sources. A wide practical applicability of betulinic acid and its derivatives demonstrated in the literature sources is also included in this review article. Several literature sources also focused on in silico calculation of physicochemical and ADME parameters of the developed compounds, and on a comparison between the experimental and calculated data.

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Section: Derivatives Of Betulinic Acid Their Pharmacological Effementioning

confidence: 99%

Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

2019

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“…It should be noted that, for many decades, alkyl aluminum compounds have been widely used in carbonyls reduction [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ] and alkenes and alkynes hydroalumination reactions [ 35 , 36 , 37 ]. i -Bu 2 AlH is commonly used in selective reduction reactions, such as the reduction of trioxohexaaza[3.3.3]propelane to saturated hexaazapropelane derivatives, regioselective transformation of the CN group to the amine or the direct reduction of carboxylic acid esters to aldehydes [ 38 , 39 , 40 ].…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation of β-Keto Sulfones to β-Hydroxy Sulfones with Alkyl Aluminum Compounds: Structure of Intermediate Hydroalumination Products

et al. 2022

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β-Hydroxy sulfones are important in organic synthesis. The simplest method of β-hydroxy sulfones synthesis is the hydrogenation of β-keto sulfones. Herein, we report the reducing properties of alkyl aluminum compounds R3Al (R = Et, i-Bu, n-Bu, t-Bu and n-Hex); i-Bu2AlH; Et2AlCl and EtAlCl2 in the hydrogenation of β-keto sulfones. The compounds i-Bu2AlH, i-Bu3Al and Et3Al are the at best reducing agents of β-keto sulfones to β-hydroxy sulfones. In reactions of β-keto sulfones with aluminum trialkyls, hydroalumination products with β-hydroxy sulfone ligands [R2AlOC(C6H5)CH2S(O)2(p-R1C6H4]n [where n = 1,2; 2aa: R = i-Bu, R1 = CH3; 2ab: R = i-Bu, R1 = Cl; 2ba: R = Et, R1 = CH3; 2bb: R = Et, R1 = Cl] and {[Et2AlOC(C6H5)CH2S(O)2(p-ClC6H4]∙Et3Al}n3bb were obtained. These complexes in the solid state have a dimeric structure, while in solutions, they appear as equilibrium monomer–dimer mixtures. The hydrolysis of both the isolated 2aa, 2ab, 2ba, 2bb and 3bb and the postreaction mixtures quantitatively leads to pure racemic β-hydroxy sulfones. Hydroalumination reaction of β-keto sulfones with alkyl aluminum compounds and subsequent hydrolysis of the complexes is a simple and very efficient method of β-hydroxy sulfones synthesis.

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Synthesis and evaluation of antiviral activities of triterpenic conjugates with 2-aminobutan-1-ol as potent microbicidal agents

et al. 2019

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Regioselective Transformation of the Cyano Group of Triterpene α,β-Alkenenitriles

Cited by 5 publications

References 15 publications

Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

Hydrogenation of β-Keto Sulfones to β-Hydroxy Sulfones with Alkyl Aluminum Compounds: Structure of Intermediate Hydroalumination Products

Synthesis and evaluation of antiviral activities of triterpenic conjugates with 2-aminobutan-1-ol as potent microbicidal agents

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