Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands

Roman O. Iakovenko, Anna N. Kazakova, Vasiliy M. Muzalevskiy, Alexander Yu. Ivanov, Irina A. Boyarskaya, Andrea Chicca, Vanessa Petrucci, Juerg Gertsch, Mikhail Krasavin, Galina L. Starova, Andrey A. Zolotarev, Margarita S. Avdontceva, Valentine G. Nenajdenko, Aleksander V. Vasilyev

Результат исследований: Научные публикации в периодических изданияхстатья

20 Цитирования (Scopus)

Выдержка

4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCH=CHCOCF3 (CF3-enones) react with arenes in excess of Bronsted superacids (TfOH, FSO3H) to give, stereoselectively, trans-1,3-diaryl-1-trifluoromethyl indanes in 35-85% yields. The reaction intermediates, the O-protonated ArCH=CHC(OH+)CF3 and the O, C-diprotonated ArHC+ CH2C(OH+) CF3 species, have been studied by means of H-1, C-13, F-19 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 c
Язык оригиналаанглийский
Страницы (с-по)8827-8842
Число страниц16
ЖурналOrganic and Biomolecular Chemistry
Том13
Номер выпуска33
DOI
СостояниеОпубликовано - 2015

Отпечаток

Cannabinoid Receptor CB2
Cannabinoid Receptors
Chemical activation
activation
Ligands
Cannabinoid Receptor CB1
Reaction intermediates
ligands
Cytotoxicity
Discrete Fourier transforms
Cations
reaction intermediates
Nuclear magnetic resonance
Electrons
affinity
cascades
selectivity
cations
nuclear magnetic resonance
electrons

Цитировать

Iakovenko, Roman O. ; Kazakova, Anna N. ; Muzalevskiy, Vasiliy M. ; Ivanov, Alexander Yu. ; Boyarskaya, Irina A. ; Chicca, Andrea ; Petrucci, Vanessa ; Gertsch, Juerg ; Krasavin, Mikhail ; Starova, Galina L. ; Zolotarev, Andrey A. ; Avdontceva, Margarita S. ; Nenajdenko, Valentine G. ; Vasilyev, Aleksander V. / Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands. В: Organic and Biomolecular Chemistry. 2015 ; Том 13, № 33. стр. 8827-8842.
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title = "Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands",
abstract = "4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCH=CHCOCF3 (CF3-enones) react with arenes in excess of Bronsted superacids (TfOH, FSO3H) to give, stereoselectively, trans-1,3-diaryl-1-trifluoromethyl indanes in 35-85{\%} yields. The reaction intermediates, the O-protonated ArCH=CHC(OH+)CF3 and the O, C-diprotonated ArHC+ CH2C(OH+) CF3 species, have been studied by means of H-1, C-13, F-19 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 c",
author = "Iakovenko, {Roman O.} and Kazakova, {Anna N.} and Muzalevskiy, {Vasiliy M.} and Ivanov, {Alexander Yu.} and Boyarskaya, {Irina A.} and Andrea Chicca and Vanessa Petrucci and Juerg Gertsch and Mikhail Krasavin and Starova, {Galina L.} and Zolotarev, {Andrey A.} and Avdontceva, {Margarita S.} and Nenajdenko, {Valentine G.} and Vasilyev, {Aleksander V.}",
year = "2015",
doi = "10.1039/c5ob01072a",
language = "English",
volume = "13",
pages = "8827--8842",
journal = "Organic and Biomolecular Chemistry",
issn = "1477-0520",
publisher = "Royal Society of Chemistry",
number = "33",

}

Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands. / Iakovenko, Roman O.; Kazakova, Anna N.; Muzalevskiy, Vasiliy M.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Chicca, Andrea; Petrucci, Vanessa; Gertsch, Juerg; Krasavin, Mikhail; Starova, Galina L.; Zolotarev, Andrey A.; Avdontceva, Margarita S.; Nenajdenko, Valentine G.; Vasilyev, Aleksander V.

В: Organic and Biomolecular Chemistry, Том 13, № 33, 2015, стр. 8827-8842.

Результат исследований: Научные публикации в периодических изданияхстатья

TY - JOUR

T1 - Reactions of CF3-enones with arenes under superelectrophilic activation: a pathway to trans-1,3-diaryl-1-CF3-indanes, new cannabinoid receptor ligands

AU - Iakovenko, Roman O.

AU - Kazakova, Anna N.

AU - Muzalevskiy, Vasiliy M.

AU - Ivanov, Alexander Yu.

AU - Boyarskaya, Irina A.

AU - Chicca, Andrea

AU - Petrucci, Vanessa

AU - Gertsch, Juerg

AU - Krasavin, Mikhail

AU - Starova, Galina L.

AU - Zolotarev, Andrey A.

AU - Avdontceva, Margarita S.

AU - Nenajdenko, Valentine G.

AU - Vasilyev, Aleksander V.

PY - 2015

Y1 - 2015

N2 - 4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCH=CHCOCF3 (CF3-enones) react with arenes in excess of Bronsted superacids (TfOH, FSO3H) to give, stereoselectively, trans-1,3-diaryl-1-trifluoromethyl indanes in 35-85% yields. The reaction intermediates, the O-protonated ArCH=CHC(OH+)CF3 and the O, C-diprotonated ArHC+ CH2C(OH+) CF3 species, have been studied by means of H-1, C-13, F-19 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 c

AB - 4-Aryl-1,1,1-trifluorobut-3-en-2-ones ArCH=CHCOCF3 (CF3-enones) react with arenes in excess of Bronsted superacids (TfOH, FSO3H) to give, stereoselectively, trans-1,3-diaryl-1-trifluoromethyl indanes in 35-85% yields. The reaction intermediates, the O-protonated ArCH=CHC(OH+)CF3 and the O, C-diprotonated ArHC+ CH2C(OH+) CF3 species, have been studied by means of H-1, C-13, F-19 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 c

U2 - 10.1039/c5ob01072a

DO - 10.1039/c5ob01072a

M3 - Article

VL - 13

SP - 8827

EP - 8842

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 33

ER -