935670-67-0Relevant academic research and scientific papers
Unusual α-hydroxyaldehyde with a cyclopentane framework from verbenol epoxide
Ardashov, Oleg V.,Il'ina, Irina V.,Korchagina, Dina V.,Volcho, Konstantin P.,Salakhutdinov, Nariman F.
, p. 303 - 305 (2007)
The isomerization of (-)-cis-verbenol epoxide in the presence of K10 clay forms optically active 2-(2,2-dimethylcyclopent- 3-enyl)-2-hydroxypropanal as one of the products.
Reaction of (-)-cis-verbenol epoxide with aromatic aldehydes over montmorillonite K10 clay
Il'Ina,Korchagina,Volcho,Salakhutdinov
, p. 998 - 1001 (2010)
Reactions of (-)-cis-verbenol epoxide with a series of para-substituted benzaldehydes in the presence of montmorillonite K10 gave mixtures of products of intra- and intermolecular transformations, whose composition depended on the initial aldehyde.
Heterogeneous catalysis for transformation of biomass derived compounds beyond fuels: Synthesis of monoterpenoid dioxinols with analgesic activity
Torozova, Alexandra,M?ki-Arvela, P?ivi,Aho, Atte,Kumar, Narendra,Smeds, Annika,Peurla, Markus,Sj?holm, Rainer,Heinmaa, Ivo,Korchagina, Dina V.,Volcho, Konstantin P.,Salakhutdinov, Nariman F.,Murzin, Dmitry Yu.
, p. 48 - 55 (2015)
Catalytic synthesis of a dioxinol compound, (2S,4aR,8R,8aR)-4,4,7-trimethyl-2-phenyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ol, exhibiting analgesic activity was demonstrated over Fe-modified beta zeolite. During interactions between cis-verbenol oxide and benzaldehyde, two main reactions occurred. In the first reaction, namely isomerization of verbenol oxide both cyclopentenic hydroxyketone, oxetane as well as a cyclohexyl compound, (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol were formed. In the second parallel reaction the target compound was generated. The highest yield of the target compound was achieved in the reaction between verbenol oxide and benzaldehyde at their molar ratio of 1:133 with the bifunctional iron modified Fe-H-Beta-150 catalyst at 70 °C giving a much higher yield than reported earlier in the literature, being 46 mol-% at complete conversion of verbenol oxide.
Synthesis and Analgesic Activity of 4,7-Dimethyl-3,4,4a,5,8,8a-Hexahydro-2-Chromen-4,8-Diols Containing Alkyl-Substituted Aromatic Moieties
Patrusheva,Pavlova,Korchagina,Tolstikova,Volcho,Salakhutdinov
, p. 1066 - 1071 (2017/11/27)
A series of new heterocyclic compounds with the hexahydro-2H-chromene skeleton were prepared by reacting the monoterpenoid para-mentha-1,8-diene-5,6-diol with 4-alkyl-substituted aromatic aldehydes. Adding small alkyl substituents (methyl and ethyl) to the aldehyde aromatic ring increased the yields of hexahydrochromenes as compared with the analogous reaction with benzaldehyde. However, adding a branched substituent (isopropyl) and longer butyl and octyl moieties reduced the yields of the target compounds. The stereoselectivity of the reaction changed as the alkyl substituent lengthened. The analgesic activity of the obtained products was studied.
Synthesis and analgesic activity of stereoisomers of 2-(3(4)-hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols
Pavlova, Alla,Mikhalchenko, Oksana,Rogachev, Artem,Il'Ina, Irina,Korchagina, Dina,Gatilov, Yuriy,Tolstikova, Tat'Yana,Volcho, Konstantin,Salakhutdinov, Nariman
, p. 3821 - 3830 (2015/10/06)
2-(3(4)-Hydroxy-4(3)-methoxyphenyl)-4,7-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-chromene-4,8-diols were found recently to possess high analgesic activity and low acute toxicity. Stereoisomers of these compounds with high optical purity were synthesized from (+)- and (-)-α-pinenes for the first time in this work. The structure of (4S)-4b isomer was confirmed by the XRD data. Studies of analgesic activity of the resulting products demonstrated that neither the absolute configuration nor cis- or trans-arrangement of vicinal oxygen atoms plays a significant role in manifestation of analgesic effect by these isomers, while only (4S)-4b isomer, but not (4R)-4b demonstrated the analgesic effect.
The First Synthesis of (4S,5R,6R)-5,6-Dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic Acid
Ardashov, Oleg V.,Demidova, Yuliya S.,Korchagina, Dina V.,Volcho, Konstantin P.,Simakova, Irina L.,Salakhutdinov, Nariman F.
, p. 1442 - 1455 (2015/10/20)
A putative acid metabolite of a novel highly effective antiparkinsonian agent, (4S,5R,6R)-5,6-dihydroxy-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid (5), was synthesized for the first time. Several synthetic approaches based on different transformations of O-bearing monoterpenoids of the pinane and p-menthane series were developed and tested in the course of the study. Acid 5 was synthesized starting from a commercially available monoterpenoid, (-)-verbenone, in a total yield of 4.4% over eight steps.
Isomerization of bicyclic terpene epoxides into allylic alcohols without changing of the initial structure
Demidova, Yu.S.,Ardashov,Simakova,Simakova,Volcho,Salakhutdinov,Murzin, D.Yu.
, p. 162 - 166 (2014/06/09)
A novel method of (1S,2R,3R,5R)-6,6-dimethyl-4-methylenebicyclo[3.1.1] heptane-2,3-diol synthesis, which is a valuable intermediate in the synthesis of a perspective potent anti-Parkinson drugs, in the presence of TiO2 was proposed. Catalytic activity of TiO2 in the bicyclic terpene epoxides isomerization to corresponding allylic alcohols without changing of the initial structure was demonstrated, contrary to titania-supported Au catalysts which promoted rearrangement with predominant formation of a cyclopentene α-hydroxy ketone.
Synthesis and analgesic activity of monoterpenoid-derived 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-ols
Kurbakova, Svetlana,Il'Ina, Irina,Pavlova, Alla,Korchagina, Dina,Yarovaya, Olga,Tolstikova, TaT'Yana,Volcho, Konstantin,Salakhutdinov, Nariman
, p. 1709 - 1717 (2014/05/06)
A new series of chiral heterocyclic compounds with frameworks of different types were synthesized by reactions of verbenol epoxide with aromatic aldehydes in the presence of montmorillonite clay. The analgesic activity of compounds with frameworks of 2-aryl-4,4,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[d][1,3] dioxin-8-ol type was studied in vivo. The majority of these compounds showed a significant analgesic activity in the acetic acid-induced writhing test; two compounds also showed analgesic activity in the hot-plate test. ED50 in acetic acid-induced writhing test for compound where aryl is 4-chlorophenyl substituent was determined to be 4.5 mg/kg. Compound with 4-nitrophenyl substituent demonstrated high analgesic activity in both tests. Springer Science+Business Media 2013.
Transformations of several monoterpenoids in the presence of aldehydes in supercritical solvents
Anikeev,Sivcev,Il'Ina,Korchagina,Statsenko,Volcho,Salakhutdinov
, p. 382 - 387 (2013/07/26)
The reactivity of verbenol epoxide and isopulegol in supercritical solvents in the presence of aromatic aldehydes was studied using a flow type reactor and a heterogeneous catalyst (Al2O3) or no catalyst. The intramolecular transformations or interactions of reagents with the solvent prevailed in all cases; the yield of the products of intermolecular reactions of terpenoids with aldehydes was up to 1%. The aldehydes did not interact with verbenol epoxide but produced a considerable effect on the distribution of its isomerization products.
Synthesis and analgesic activity of new heterocyclic compounds derived from monoterpenoids
Mikhalchenko, Oksana,Il'Ina, Irina,Pavlova, Alla,Morozova, Ekaterina,Korchagina, Dina,Tolstikova, Tat'Yana,Pokushalov, Evgeny,Volcho, Konstantin,Salakhutdinov, Nariman
, p. 3026 - 3034 (2013/07/26)
A set of new heterocyclic compounds with different types of framework, including a new type of framework, were synthesized by reactions of verbenol epoxide and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol with aromatic aldehydes containing three methoxy groups. The analgesic activity of these substances was studied. Three compounds possessed considerable activity in vivo in the acetic acid-induced writhing test. (2S,4R,4aR,8S,8aR)-4,7-Dimethyl- 2-(2,4,5-trimethoxyphenyl)-3,4,4a,5,8,8a-hexahydro-2H-4,8-epoxychromene exhibited high analgesic activity in both acetic acid-induced writhing and hot plate tests; its selectivity index IS50 exceeded 60.
