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Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity. / Iakovenko, Roman O.; Chicca, Andrea; Nieri, Daniela; Reynoso-Moreno, Ines; Gertsch, Jürg; Krasavin, Mikhail; Vasilyev, Aleksander V.

In: Tetrahedron, Vol. 75, No. 5, 01.02.2019, p. 624-632.

Research output: Contribution to journal › Article › peer-review

Harvard

Iakovenko, RO, Chicca, A, Nieri, D, Reynoso-Moreno, I, Gertsch, J, Krasavin, M & Vasilyev, AV 2019, 'Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity', Tetrahedron, vol. 75, no. 5, pp. 624-632. https://doi.org/10.1016/j.tet.2018.12.041

APA

Iakovenko, R. O., Chicca, A., Nieri, D., Reynoso-Moreno, I., Gertsch, J., Krasavin, M., & Vasilyev, A. V. (2019). Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity. Tetrahedron, 75(5), 624-632. https://doi.org/10.1016/j.tet.2018.12.041

Vancouver

Iakovenko RO, Chicca A, Nieri D, Reynoso-Moreno I, Gertsch J, Krasavin M et al. Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity. Tetrahedron. 2019 Feb 1;75(5):624-632. https://doi.org/10.1016/j.tet.2018.12.041

Author

Iakovenko, Roman O. ; Chicca, Andrea ; Nieri, Daniela ; Reynoso-Moreno, Ines ; Gertsch, Jürg ; Krasavin, Mikhail ; Vasilyev, Aleksander V. / Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity. In: Tetrahedron. 2019 ; Vol. 75, No. 5. pp. 624-632.

BibTeX

@article{fad071f0db104435a4ef19ae452d0367,
title = "Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity",
abstract = " A series of 1-trifluoromethyl substituted indanes and indenes bearing aryl groups in positions 1 and/or 3 of the indane core have been synthesized mainly by electrophilic cyclization and arylation of the corresponding trifluoromethylated allyl and propargyl alcohols. The distinctly lipophilic compounds thus obtained were tested against various components of human endocannabinoid system. None of the compounds displayed affinity toward CB 1 or CB 2 receptors. Two compounds inhibited monoacylglycerol lipase (MAGL) and three compounds showed inhibition of anandamide (AEA) uptake. The latter can be related to the low-micromolar inhibition of fatty acid amide hydrolase (FAAH) inhibition displayed by one of these compounds. ",
keywords = "Biological activity, Indanes, Indenes, Trifluoromethyl group, FAAH, PROMOTED REACTIONS, ARENES, DISCOVERY, KETONES, ALLYL ALCOHOLS, STEREOSELECTIVE-SYNTHESIS, INHIBITORS, GRIGNARD-REAGENTS",
author = "Iakovenko, {Roman O.} and Andrea Chicca and Daniela Nieri and Ines Reynoso-Moreno and J{\"u}rg Gertsch and Mikhail Krasavin and Vasilyev, {Aleksander V.}",
year = "2019",
month = feb,
day = "1",
doi = "10.1016/j.tet.2018.12.041",
language = "English",
volume = "75",
pages = "624--632",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "5",

}

RIS

TY - JOUR

T1 - Synthesis of various arylated trifluoromethyl substituted indanes and indenes, and study of their biological activity

AU - Iakovenko, Roman O.

AU - Chicca, Andrea

AU - Nieri, Daniela

AU - Reynoso-Moreno, Ines

AU - Gertsch, Jürg

AU - Krasavin, Mikhail

AU - Vasilyev, Aleksander V.

PY - 2019/2/1

Y1 - 2019/2/1

N2 - A series of 1-trifluoromethyl substituted indanes and indenes bearing aryl groups in positions 1 and/or 3 of the indane core have been synthesized mainly by electrophilic cyclization and arylation of the corresponding trifluoromethylated allyl and propargyl alcohols. The distinctly lipophilic compounds thus obtained were tested against various components of human endocannabinoid system. None of the compounds displayed affinity toward CB 1 or CB 2 receptors. Two compounds inhibited monoacylglycerol lipase (MAGL) and three compounds showed inhibition of anandamide (AEA) uptake. The latter can be related to the low-micromolar inhibition of fatty acid amide hydrolase (FAAH) inhibition displayed by one of these compounds.

AB - A series of 1-trifluoromethyl substituted indanes and indenes bearing aryl groups in positions 1 and/or 3 of the indane core have been synthesized mainly by electrophilic cyclization and arylation of the corresponding trifluoromethylated allyl and propargyl alcohols. The distinctly lipophilic compounds thus obtained were tested against various components of human endocannabinoid system. None of the compounds displayed affinity toward CB 1 or CB 2 receptors. Two compounds inhibited monoacylglycerol lipase (MAGL) and three compounds showed inhibition of anandamide (AEA) uptake. The latter can be related to the low-micromolar inhibition of fatty acid amide hydrolase (FAAH) inhibition displayed by one of these compounds.

KW - Biological activity

KW - Indanes

KW - Indenes

KW - Trifluoromethyl group

KW - FAAH

KW - PROMOTED REACTIONS

KW - ARENES

KW - DISCOVERY

KW - KETONES

KW - ALLYL ALCOHOLS

KW - STEREOSELECTIVE-SYNTHESIS

KW - INHIBITORS

KW - GRIGNARD-REAGENTS

UR - http://www.scopus.com/inward/record.url?scp=85059182733&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/synthesis-various-arylated-trifluoromethyl-substituted-indanes-indenes-study-biological-activity

U2 - 10.1016/j.tet.2018.12.041

DO - 10.1016/j.tet.2018.12.041

M3 - Article

AN - SCOPUS:85059182733

VL - 75

SP - 624

EP - 632

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 5

ER -

ID: 39973851