Synthesis of hydroxy derivatives of limonene

Ardashov, Oleg V.; Волчо, К. П.; Salakhutdinov, N. F.

doi:10.1070/rc2014v083n04abeh004383

Cited by 9 publications

(5 citation statements)

References 92 publications

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“…A variety of very interesting derivatives was obtained depending on the biocatalyst used. Some of them are very important for their application in perfumery, cosmetics, food and pharmaceutical industries e.g., menthol, terpinen-4-ol [ 74 , 75 , 76 , 77 , 78 ].…”

Section: Discussionmentioning

confidence: 99%

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

et al. 2020

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The main objective of this article was to present the possibilities of using the enzymatic system of microorganisms and insects to transform small molecules, such as monoterpenes. The most important advantage of this type of reaction is the possibility of obtaining derivatives that are not possible to obtain with standard methods of organic synthesis or are very expensive to obtain. The interest of industrial centers focuses mainly on obtaining particles of high optical purity, which have the desired biological properties. The cost of obtaining such a compound and the elimination of toxic or undesirable chemical waste is important. Enzymatic reactions based on enzymes alone or whole microorganisms enable obtaining products with a specific structure and purity in accordance with the rules of Green Chemistry.

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Section: Discussionmentioning

confidence: 99%

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

et al. 2020

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“…It is important that, unlike epoxides 5 – 7 and other epoxides of similar structure, , compound 4 is unusually stable in acidic conditions such as 10% H 2 SO 4 or montmorillonite clay K10.…”

Section: Resultsmentioning

confidence: 99%

A Novel Small Molecule Supports the Survival of Cultured Dopamine Neurons and May Restore the Dopaminergic Innervation of the Brain in the MPTP Mouse Model of Parkinson’s Disease

Ardashov

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Mahato

et al. 2019

ACS Chem. Neurosci.

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We previously showed that monoterpenoid (1R,2R,6S)-3-methyl-6-(prop-1-en-2yl)cyclohex-3-ene-1,2-diol 1 alleviates motor manifestations of Parkinson's disease in animal models. In the present study, we designed and synthesized monoepoxides of (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 1 and evaluated their biological activity in the MPTP mouse model of Parkinson's disease. We also assessed the ability of these compounds to penetrate the blood brain barrier (BBB). According to these data, we choose epoxide 4, which potently restored locomotor activity in MPTP-treated mice and penetrated the BBB with high efficacy, to further explore the potential mechanism of action. Epoxide 4 was found to robustly promote the survival of cultured dopamine neurons, protect dopamine neurons from toxin-induced degeneration and trigger the mitogen-activated protein kinase (MAPK) signaling cascade in cells of neuronal 2 origin. Meanwhile, neither survival-promoting effect nor MAPK activation was observed in nonneuronal cells treated with epoxide 4. In the MPTP mice model of Parkinson's disease, compound 4 increased the density of fibers expressing the key enzyme of dopamine synthesis, tyrosine hydroxylase. Taken together, these data indicate that epoxide 4 can be a promising compound for further development not only as symptomatic treatment but also as a disease-modifying drug to treat Parkinson's disease.

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“…We synthesized earlier hydroxyderivatives 2 [8] and 3 [9]. The methods for synthesizing these and other similar alcohols were recently reviewed by us in detail [10].The goal of the present work was to synthesize 10-carbonyl and 10-carboxylic derivatives of 1. The first task was to prepare 2-[(1S,5R,6R)-5,6-dihydroxy-4-methylcyclohex-3-enyl]acrylaldehyde (3).…”

mentioning

confidence: 98%

“…We synthesized earlier hydroxyderivatives 2 [8] and 3 [9]. The methods for synthesizing these and other similar alcohols were recently reviewed by us in detail [10].…”

mentioning

confidence: 99%

Synthesis of 10-Carbonyl and 10-Carboxylic Derivatives of para-Mentha-1,8-Diene-5,6-Diol

et al. 2015

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The synthesis of 10-carbonyl and 10-carboxylic derivatives of para-mentha-1,8-diene-5,6-diol (1) that exhibited high anti-Parkinson's activity was described. The synthesis of these compounds was an important programmatic component in a study of the metabolism of 1.Our previous discovery [1, 2] that (4S,5R,6R)-para-mentha-1,8-diene-5,6-diol (1) exhibited high anti-Parkinson's activity stimulated further studies of it. The absolute configuration of 1 affected its anti-Parkinson's activity [1]. It was important to include all functional groups (double bonds and hydroxyls) in the molecule [3]. Metabolism studies represent a key phase of pharmacokinetic investigations. As a rule, mass spectra of monoterpenoids are very difficult to relate reliably to their structures without mass spectrometric data of the pure compounds, which makes it necessary to synthesize them.According to literature data on the metabolism of para-menthane monoterpenoids [4][5][6][7], the formation of products from methyl hydroxylation and further oxidation to carbonyl compounds were expected. We synthesized earlier hydroxyderivatives 2 [8] and 3 [9]. The methods for synthesizing these and other similar alcohols were recently reviewed by us in detail [10].The goal of the present work was to synthesize 10-carbonyl and 10-carboxylic derivatives of 1. The first task was to prepare 2-[(1S,5R,6R)-5,6-dihydroxy-4-methylcyclohex-3-enyl]acrylaldehyde (3). The simplest approach seemed to involve oxidation of triol 2. However, its reaction with MnO 2 formed reaction mixtures with <30% of target aldehyde 3 according to PMR and GC-MS data.We used bromide 4 as a key intermediate in the synthesis of triol 2 [8]. Also, bromides are known to be capable of transforming into the corresponding aldehydes via alkylation of nitro compounds followed by Nef hydrolysis [11,12] or Kornblum oxidation by 14]. However, instead of the expected reaction with EtNO 2 , 4 underwent an intramolecular heterocyclization to form bicyclic product 5 in quantitative yield (Scheme 1). We prepared previously 5 in 15% yield via the reaction of 4 with n-BuLi [8]. Thus, the newly found version for performing the intramolecular cyclization turned out to be much more effective. Kornblum oxidation of 5 via reaction with DMSO in CCl 4 formed a complicated product mixture with total contents of identified 3 and 5 of <7%. 1) N. N. VorozhtsovOH OH 1 3 5 9 7 OH OH OH OH OH O 1 2 3

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Synthesis of hydroxy derivatives of limonene

Cited by 9 publications

References 92 publications

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

A Novel Small Molecule Supports the Survival of Cultured Dopamine Neurons and May Restore the Dopaminergic Innervation of the Brain in the MPTP Mouse Model of Parkinson’s Disease

Synthesis of 10-Carbonyl and 10-Carboxylic Derivatives of para-Mentha-1,8-Diene-5,6-Diol

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