title: Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands
metadata.name: dc.contributor.author
metadata.value: Iakovenko, Roman O.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Kazakova, Anna N.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Muzalevskiy, Vasiliy M.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Ivanov, Alexander Yu.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Boyarskaya, Irina A.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Chicca, Andrea
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Petrucci, Vanessa
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Gertsch, Jürg
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Krasavin, Mikhail
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Starova, Galina L.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Zolotarev, Andrey A.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Avdontceva, Margarita S.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Nenajdenko, Valentine G.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Vasilyev, Aleksander V.
metadata.lang: -
metadata.name: dc.date.accessioned
metadata.value: 2016-04-10T19:33:54Z
metadata.lang: -
metadata.name: dc.date.available
metadata.value: 2016-04-10T19:33:54Z
metadata.lang: -
metadata.name: dc.date.issued
metadata.value: 2015
metadata.lang: -
metadata.name: dc.identifier.issn
metadata.value: 1477-0520
metadata.lang: -
metadata.name: dc.identifier.uri
metadata.value: http://hdl.handle.net/11701/2040
metadata.lang: -
metadata.name: dc.description.abstract
metadata.value: 4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCHvCHCOCF3 (CF3-enones) react with arenes in excess of  Brønsted superacids (TfOH, FSO3H) to give, stereoselectively, trans-1,3-diaryl-1-trifluoromethyl indanes in
  35–85% yields. The reaction intermediates, the O-protonated ArCHvCHC(OH+)CF3 and the O,C-diprotonated ArHC+CH2C(OH+)CF3 species, have been studied by means of 1H, 13C, 19F NMR, and DFT calculations. Both types of the cations may participate in the reaction, depending on their electrophilicity and
  electron-donating properties of the arenes. The formation of CF3-indanes is a result of cascade reaction
  of protonated CF3-enones to form chemo-, regio- and stereoselectively three new C–C bonds. The
  obtained trans-1,3-diaryl-1-trifluoromethyl indanes were investigated as potential ligands for cannabinoid
  receptors CB1 and CB2 types. The most potent compound showed sub-micromolar affinity for both
  receptor subtypes with a 6-fold selectivity toward the CB2 receptor with no appreciable cytotoxicity
  toward SHSY5Y cells.
metadata.lang: en_GB
metadata.name: dc.description.sponsorship
metadata.value: This work was supported by Saint Petersburg State University (grant no. 12.50.1558.2013, and 12.38.195.2014).
metadata.lang: en_GB
metadata.name: dc.language.iso
metadata.value: en
metadata.lang: en_GB
metadata.name: dc.publisher
metadata.value: The Royal Society of Chemistry
metadata.lang: en_GB
metadata.name: dc.relation.ispartofseries
metadata.value: Org. Biomol. Chem.,;13, pp. 8827–8842
metadata.lang: -
metadata.name: dc.subject
metadata.value: 4-Aryl-1,1,1-trifluorobut-3-en-2-ones
metadata.lang: en_GB
metadata.name: dc.subject
metadata.value: arenes
metadata.lang: en_GB
metadata.name: dc.subject
metadata.value: Brønsted superacids
metadata.lang: en_GB
metadata.name: dc.subject
metadata.value: superelectrophilic activation
metadata.lang: en_GB
metadata.name: dc.title
metadata.value: Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands
metadata.lang: en_GB
metadata.name: dc.type
metadata.value: Article
metadata.lang: en_GB
resources.filename: Org Bio Mol, 2015.pdf
resources.url: https://dspace.spbu.ru/bitstream/11701/2040/1/Org%20Bio%20Mol%2c%202015.pdf
resources.format: Adobe PDF
resources.size: 2,5 MB