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Effect of chiral polyhydrochromenes on cannabinoid system. / Li-Zhulanov, Nikolai S.; Il’ina, Irina V.; Chicca, Andrea et al.

In: Medicinal Chemistry Research, Vol. 28, No. 4, 04.2019, p. 450-464.

Research output: Contribution to journalArticlepeer-review

Harvard

Li-Zhulanov, NS, Il’ina, IV, Chicca, A, Schenker, P, Patrusheva, OS, Nazimova, EV, Korchagina, DV, Krasavin, M, Volcho, KP & Salakhutdinov, NF 2019, 'Effect of chiral polyhydrochromenes on cannabinoid system', Medicinal Chemistry Research, vol. 28, no. 4, pp. 450-464. https://doi.org/10.1007/s00044-019-02294-9

APA

Li-Zhulanov, N. S., Il’ina, I. V., Chicca, A., Schenker, P., Patrusheva, O. S., Nazimova, E. V., Korchagina, D. V., Krasavin, M., Volcho, K. P., & Salakhutdinov, N. F. (2019). Effect of chiral polyhydrochromenes on cannabinoid system. Medicinal Chemistry Research, 28(4), 450-464. https://doi.org/10.1007/s00044-019-02294-9

Vancouver

Li-Zhulanov NS, Il’ina IV, Chicca A, Schenker P, Patrusheva OS, Nazimova EV et al. Effect of chiral polyhydrochromenes on cannabinoid system. Medicinal Chemistry Research. 2019 Apr;28(4):450-464. doi: 10.1007/s00044-019-02294-9

Author

Li-Zhulanov, Nikolai S. ; Il’ina, Irina V. ; Chicca, Andrea et al. / Effect of chiral polyhydrochromenes on cannabinoid system. In: Medicinal Chemistry Research. 2019 ; Vol. 28, No. 4. pp. 450-464.

BibTeX

@article{198e2ee37c17496ab316acc10649e998,
title = "Effect of chiral polyhydrochromenes on cannabinoid system",
abstract = "A set of chiral polyhydrochromenes was synthesized by clay-catalyzed reactions of monoterpenoids (−)-isopulegol, (+)-neoisopulegol and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 5 with aromatic and heteroaromatic aldehydes. These compounds resemble in structure phytocannabinoids, some of them demonstrated analgesic activity in vivo. Polyhydrochromenes containing amino groups were obtained through the interaction of (−)-isopulegol with 5-hydroxymethylfurfural, followed by substitution of hydroxy-group with bromine and further reaction with amines. The ability of all synthesized compounds to influence the endocannabinoid system was studied for the first time. Although the polyhydrochromenes did not significantly bind to CB1 and CB2 cannabinoid receptors and did not inhibit MAGL activity at the concentration of 10 µM, isopulegol derivative 2i containing 3-bromothiophene substituent inhibited FAAH activity with an IC50 value of 7.6 µM. Thus, this compound may increase endocannabinoid system activity.",
keywords = "Aldehyde, Anandamide, CB, Fatty acid amide hydrolase (FAAH), Isopulegol, Monoacylglycerol lipase (MAGL), METHOXY GROUPS, OCTAHYDRO-2H-CHROMEN-4-OL, RECEPTOR, ISOPULEGOL, MODEL, CB2, CB1, INHIBITION, ACID AMIDE HYDROLASE, VANILLIN, POTENT ANALGESIC ACTIVITY, CATALYZED PRINS",
author = "Li-Zhulanov, {Nikolai S.} and Il{\textquoteright}ina, {Irina V.} and Andrea Chicca and Patricia Schenker and Patrusheva, {Oksana S.} and Nazimova, {Ekaterina V.} and Korchagina, {Dina V.} and Mikhail Krasavin and Volcho, {Konstantin P.} and Salakhutdinov, {Nariman F.}",
note = "Publisher Copyright: {\textcopyright} 2019, Springer Science+Business Media, LLC, part of Springer Nature.",
year = "2019",
month = apr,
doi = "10.1007/s00044-019-02294-9",
language = "English",
volume = "28",
pages = "450--464",
journal = "Medicinal Chemistry Research",
issn = "1054-2523",
publisher = "Springer Nature",
number = "4",

}

RIS

TY - JOUR

T1 - Effect of chiral polyhydrochromenes on cannabinoid system

AU - Li-Zhulanov, Nikolai S.

AU - Il’ina, Irina V.

AU - Chicca, Andrea

AU - Schenker, Patricia

AU - Patrusheva, Oksana S.

AU - Nazimova, Ekaterina V.

AU - Korchagina, Dina V.

AU - Krasavin, Mikhail

AU - Volcho, Konstantin P.

AU - Salakhutdinov, Nariman F.

N1 - Publisher Copyright: © 2019, Springer Science+Business Media, LLC, part of Springer Nature.

PY - 2019/4

Y1 - 2019/4

N2 - A set of chiral polyhydrochromenes was synthesized by clay-catalyzed reactions of monoterpenoids (−)-isopulegol, (+)-neoisopulegol and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 5 with aromatic and heteroaromatic aldehydes. These compounds resemble in structure phytocannabinoids, some of them demonstrated analgesic activity in vivo. Polyhydrochromenes containing amino groups were obtained through the interaction of (−)-isopulegol with 5-hydroxymethylfurfural, followed by substitution of hydroxy-group with bromine and further reaction with amines. The ability of all synthesized compounds to influence the endocannabinoid system was studied for the first time. Although the polyhydrochromenes did not significantly bind to CB1 and CB2 cannabinoid receptors and did not inhibit MAGL activity at the concentration of 10 µM, isopulegol derivative 2i containing 3-bromothiophene substituent inhibited FAAH activity with an IC50 value of 7.6 µM. Thus, this compound may increase endocannabinoid system activity.

AB - A set of chiral polyhydrochromenes was synthesized by clay-catalyzed reactions of monoterpenoids (−)-isopulegol, (+)-neoisopulegol and (1R,2R,6S)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 5 with aromatic and heteroaromatic aldehydes. These compounds resemble in structure phytocannabinoids, some of them demonstrated analgesic activity in vivo. Polyhydrochromenes containing amino groups were obtained through the interaction of (−)-isopulegol with 5-hydroxymethylfurfural, followed by substitution of hydroxy-group with bromine and further reaction with amines. The ability of all synthesized compounds to influence the endocannabinoid system was studied for the first time. Although the polyhydrochromenes did not significantly bind to CB1 and CB2 cannabinoid receptors and did not inhibit MAGL activity at the concentration of 10 µM, isopulegol derivative 2i containing 3-bromothiophene substituent inhibited FAAH activity with an IC50 value of 7.6 µM. Thus, this compound may increase endocannabinoid system activity.

KW - Aldehyde

KW - Anandamide

KW - CB

KW - Fatty acid amide hydrolase (FAAH)

KW - Isopulegol

KW - Monoacylglycerol lipase (MAGL)

KW - METHOXY GROUPS

KW - OCTAHYDRO-2H-CHROMEN-4-OL

KW - RECEPTOR

KW - ISOPULEGOL

KW - MODEL

KW - CB2

KW - CB1

KW - INHIBITION

KW - ACID AMIDE HYDROLASE

KW - VANILLIN

KW - POTENT ANALGESIC ACTIVITY

KW - CATALYZED PRINS

UR - http://www.scopus.com/inward/record.url?scp=85061005323&partnerID=8YFLogxK

U2 - 10.1007/s00044-019-02294-9

DO - 10.1007/s00044-019-02294-9

M3 - Article

AN - SCOPUS:85061005323

VL - 28

SP - 450

EP - 464

JO - Medicinal Chemistry Research

JF - Medicinal Chemistry Research

SN - 1054-2523

IS - 4

ER -

ID: 18487363