1292847-80-3Relevant academic research and scientific papers
Synthesis and cytotoxic activity of substituted hexahydro-2H-4,6-(epoxymethano)chromen-8(5H)-ones obtained from (–)-verbenone
Il’ina,Pokrovsky,Mikhalchenko,Korchagina,Volcho,Pokrovsky,Salakhutdinov
, p. 2257 - 2260 (2016/10/03)
A number of compounds with a substituted hexahydro-2H-4,6-(epoxymethano)chromen8(5H)-one framework was synthesized starting from monoterpenoid (–)-verbenone and aromatic aldehydes containing methoxy and hydroxy groups. Cytotoxic activity of these compounds on human tumor cell lines was studied for the first time. Compounds containing three methoxy groups in each aromatic ring were found to be the most promising for further studies.
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.
Potent neuroprotective activity of monoterpene derived 4-[(3aR,7aS)-1,3,3a, 4,5,7a-hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol in MPTP mice model
Pavlova, Alla V.,Ilìna, Irina V.,Morozova, Ekaterina A.,Korchagina, Dina V.,Kurbakova, Svetlana Yu.,Sorokina, Irina V.,Tolstikova, Tatyana G.,Volcho, Konstantin P.,Salakhutdinov, Nariman F.
, p. 611 - 617 (2014/05/20)
Studies of the neuroprotective activity of a series of monoterpene-derived compounds on the MPTP mice model showed that 4-[(3aR,7aS)-1,3,3a,4,5,7a- hexahydro-3,3,6-trimethylisobenzofuran-1-yl]-2-methoxyphenol 15 possessed a considerable neuroprotective activity. Compound 15 was synthesized by one-stage reaction of (+)-2-carene with vanillin. It has low acute toxicity and significantly decreased the development of catalepsy evoked by haloperidol in rats.
Reactions of verbenol epoxide with aromatic aldehydes containing hydroxy or methoxy groups in the presence of montmorillonite clay
Il'ina, Irina V.,Volcho, Konstantin P.,Mikhalchenko, Oksana S.,Korchagina, Dina V.,Salakhutdinov, Nariman F.
experimental part, p. 502 - 513 (2011/04/25)
The reactions of (-)-cis-verbenol epoxide with a number of aromatic aldehydes containing OH and/or MeO groups in the presence of montmorillonite K10 clay have been studied. Several new O-containing heterocyclic compounds with different frameworks, including compounds with a previously unknown octahydro-2H-4,6-(epoxymethano)chromene framework, have been synthesized. Introduction of one donor substituent in the benzaldehyde molecule led to a decrease in the total yield of intermolecular by formed products, while the introduction of two and more substituents led to an increase in the yield of these products.
