Effect of chiral polyhydrochromenes on cannabinoid system View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-04

AUTHORS

Nikolai S. Li-Zhulanov, Irina V. Il’ina, Andrea Chicca, Patricia Schenker, Oksana S. Patrusheva, Ekaterina V. Nazimova, Dina V. Korchagina, Mikhail Krasavin, Konstantin P. Volcho, Nariman F. Salakhutdinov

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. More... »

PAGES

450-464

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00044-019-02294-9

DOI

http://dx.doi.org/10.1007/s00044-019-02294-9

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1111833582


Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
Incoming Citations Browse incoming citations for this publication using opencitations.net

JSON-LD is the canonical representation for SciGraph data.

TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

[
  {
    "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
    "about": [
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0305", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Organic Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Novosibirsk State University", 
          "id": "https://www.grid.ac/institutes/grid.4605.7", 
          "name": [
            "Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation", 
            "Novosibirsk State University, Pirogova st. 1, 630090, Novosibirsk, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Li-Zhulanov", 
        "givenName": "Nikolai S.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Novosibirsk State University", 
          "id": "https://www.grid.ac/institutes/grid.4605.7", 
          "name": [
            "Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation", 
            "Novosibirsk State University, Pirogova st. 1, 630090, Novosibirsk, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Il\u2019ina", 
        "givenName": "Irina V.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "University of Bern", 
          "id": "https://www.grid.ac/institutes/grid.5734.5", 
          "name": [
            "Institute of Biochemistry and Molecular Medicine, NCCR TransCure, University of Bern, B\u00fchlstrasse 28, 3012, Bern, Switzerland"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Chicca", 
        "givenName": "Andrea", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "University of Bern", 
          "id": "https://www.grid.ac/institutes/grid.5734.5", 
          "name": [
            "Institute of Biochemistry and Molecular Medicine, NCCR TransCure, University of Bern, B\u00fchlstrasse 28, 3012, Bern, Switzerland"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Schenker", 
        "givenName": "Patricia", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Novosibirsk Institute of Organic Chemistry", 
          "id": "https://www.grid.ac/institutes/grid.419817.2", 
          "name": [
            "Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Patrusheva", 
        "givenName": "Oksana S.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Novosibirsk Institute of Organic Chemistry", 
          "id": "https://www.grid.ac/institutes/grid.419817.2", 
          "name": [
            "Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Nazimova", 
        "givenName": "Ekaterina V.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Novosibirsk Institute of Organic Chemistry", 
          "id": "https://www.grid.ac/institutes/grid.419817.2", 
          "name": [
            "Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Korchagina", 
        "givenName": "Dina V.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Saint Petersburg State University", 
          "id": "https://www.grid.ac/institutes/grid.15447.33", 
          "name": [
            "Saint Petersburg State University, 199034, Saint Petersburg, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Krasavin", 
        "givenName": "Mikhail", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Novosibirsk State University", 
          "id": "https://www.grid.ac/institutes/grid.4605.7", 
          "name": [
            "Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation", 
            "Novosibirsk State University, Pirogova st. 1, 630090, Novosibirsk, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Volcho", 
        "givenName": "Konstantin P.", 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Novosibirsk State University", 
          "id": "https://www.grid.ac/institutes/grid.4605.7", 
          "name": [
            "Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation", 
            "Novosibirsk State University, Pirogova st. 1, 630090, Novosibirsk, Russian Federation"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Salakhutdinov", 
        "givenName": "Nariman F.", 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1007/s00044-016-1573-3", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1000429983", 
          "https://doi.org/10.1007/s00044-016-1573-3"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.bmc.2016.08.037", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1004572214"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.ejphar.2016.02.010", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1008053410"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.molcata.2016.01.010", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1008512306"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s00044-012-0310-9", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1010933253", 
          "https://doi.org/10.1007/s00044-012-0310-9"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1111/jcpt.12235", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1012946129"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.bcp.2014.09.020", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1013542526"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1124/jpet.108.143487", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1014104448"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1523/jneurosci.3326-06.2006", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1015323262"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1074/jbc.m112.373241", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1015507806"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/s0040-4020(01)80157-5", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1018680828"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1590/s0103-50532010000800023", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1018789759"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s00044-015-1426-5", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1019979354", 
          "https://doi.org/10.1007/s00044-015-1426-5"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.carres.2013.01.012", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1022211704"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/hlca.200790042", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1022290001"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.molcata.2015.09.021", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1023981463"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1039/c1ob00033k", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1027000983"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.molcata.2014.11.016", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1029650154"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s00044-014-1071-4", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1031982382", 
          "https://doi.org/10.1007/s00044-014-1071-4"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s10600-016-1785-2", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1033443662", 
          "https://doi.org/10.1007/s10600-016-1785-2"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s10600-016-1785-2", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1033443662", 
          "https://doi.org/10.1007/s10600-016-1785-2"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1124/jpet.112.201426", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1034322426"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.tetlet.2009.02.202", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1034503366"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1038/npp.2015.336", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1042379188", 
          "https://doi.org/10.1038/npp.2015.336"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.tetlet.2010.03.100", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1042907850"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/hlca.201000269", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1043172115"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.chemrev.5b00411", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055085189"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jm500220s", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055954659"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1055/s-0032-1316915", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1057266049"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3762/bjoc.12.64", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1071380259"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://app.dimensions.ai/details/publication/pub.1082964580", 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.2174/1570180813666161102142642", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1084832943"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s10600-017-1966-7", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1084937522", 
          "https://doi.org/10.1007/s10600-017-1966-7"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s10600-017-1966-7", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1084937522", 
          "https://doi.org/10.1007/s10600-017-1966-7"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.neuropharm.2017.05.018", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1085432102"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1111/bph.13887", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1085593650"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1073/pnas.1704065114", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1085870515"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.neuropharm.2017.06.015", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1086043553"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jmedchem.7b01845", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1100238414"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/acs.jmedchem.7b01845", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1100238414"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.tetlet.2018.01.040", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1100741724"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.tetlet.2018.01.040", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1100741724"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.tetlet.2018.01.040", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1100741724"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1016/j.mcat.2018.05.007", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1103944803"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.3389/fnmol.2018.00180", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1104260804"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1070/rcr4810", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1104337222"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1002/cctc.201800974", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1105467115"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2019-04", 
    "datePublishedReg": "2019-04-01", 
    "description": "A set of chiral polyhydrochromenes was synthesized by clay-catalyzed reactions of monoterpenoids (\u2212)-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 (\u2212)-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 \u00b5M, isopulegol derivative 2i containing 3-bromothiophene substituent inhibited FAAH activity with an IC50 value of 7.6 \u00b5M. Thus, this compound may increase endocannabinoid system activity.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1007/s00044-019-02294-9", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isFundedItemOf": [
      {
        "id": "sg:grant.4896814", 
        "type": "MonetaryGrant"
      }
    ], 
    "isPartOf": [
      {
        "id": "sg:journal.1102690", 
        "issn": [
          "1054-2523", 
          "1554-8120"
        ], 
        "name": "Medicinal Chemistry Research", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "4", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "28"
      }
    ], 
    "name": "Effect of chiral polyhydrochromenes on cannabinoid system", 
    "pagination": "450-464", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "19957fc42df7aa6eb9a68dd4c72d0f121fbcb64a0cf850d4cd272e2da3dde83b"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/s00044-019-02294-9"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1111833582"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/s00044-019-02294-9", 
      "https://app.dimensions.ai/details/publication/pub.1111833582"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-11T13:21", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000368_0000000368/records_78974_00000001.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://link.springer.com/10.1007%2Fs00044-019-02294-9"
  }
]
 

Download the RDF metadata as:  json-ld nt turtle xml License info

HOW TO GET THIS DATA PROGRAMMATICALLY:

JSON-LD is a popular format for linked data which is fully compatible with JSON.

curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02294-9'

N-Triples is a line-based linked data format ideal for batch operations.

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02294-9'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02294-9'

RDF/XML is a standard XML format for linked data.

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s00044-019-02294-9'


 

This table displays all metadata directly associated to this object as RDF triples.

258 TRIPLES      21 PREDICATES      69 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/s00044-019-02294-9 schema:about anzsrc-for:03
2 anzsrc-for:0305
3 schema:author N8d92ccfed5844e3da9ecc0c605a70c03
4 schema:citation sg:pub.10.1007/s00044-012-0310-9
5 sg:pub.10.1007/s00044-014-1071-4
6 sg:pub.10.1007/s00044-015-1426-5
7 sg:pub.10.1007/s00044-016-1573-3
8 sg:pub.10.1007/s10600-016-1785-2
9 sg:pub.10.1007/s10600-017-1966-7
10 sg:pub.10.1038/npp.2015.336
11 https://app.dimensions.ai/details/publication/pub.1082964580
12 https://doi.org/10.1002/cctc.201800974
13 https://doi.org/10.1002/hlca.200790042
14 https://doi.org/10.1002/hlca.201000269
15 https://doi.org/10.1016/j.bcp.2014.09.020
16 https://doi.org/10.1016/j.bmc.2016.08.037
17 https://doi.org/10.1016/j.carres.2013.01.012
18 https://doi.org/10.1016/j.ejphar.2016.02.010
19 https://doi.org/10.1016/j.mcat.2018.05.007
20 https://doi.org/10.1016/j.molcata.2014.11.016
21 https://doi.org/10.1016/j.molcata.2015.09.021
22 https://doi.org/10.1016/j.molcata.2016.01.010
23 https://doi.org/10.1016/j.neuropharm.2017.05.018
24 https://doi.org/10.1016/j.neuropharm.2017.06.015
25 https://doi.org/10.1016/j.tetlet.2009.02.202
26 https://doi.org/10.1016/j.tetlet.2010.03.100
27 https://doi.org/10.1016/j.tetlet.2018.01.040
28 https://doi.org/10.1016/s0040-4020(01)80157-5
29 https://doi.org/10.1021/acs.chemrev.5b00411
30 https://doi.org/10.1021/acs.jmedchem.7b01845
31 https://doi.org/10.1021/jm500220s
32 https://doi.org/10.1039/c1ob00033k
33 https://doi.org/10.1055/s-0032-1316915
34 https://doi.org/10.1070/rcr4810
35 https://doi.org/10.1073/pnas.1704065114
36 https://doi.org/10.1074/jbc.m112.373241
37 https://doi.org/10.1111/bph.13887
38 https://doi.org/10.1111/jcpt.12235
39 https://doi.org/10.1124/jpet.108.143487
40 https://doi.org/10.1124/jpet.112.201426
41 https://doi.org/10.1523/jneurosci.3326-06.2006
42 https://doi.org/10.1590/s0103-50532010000800023
43 https://doi.org/10.2174/1570180813666161102142642
44 https://doi.org/10.3389/fnmol.2018.00180
45 https://doi.org/10.3762/bjoc.12.64
46 schema:datePublished 2019-04
47 schema:datePublishedReg 2019-04-01
48 schema:description 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.
49 schema:genre research_article
50 schema:inLanguage en
51 schema:isAccessibleForFree false
52 schema:isPartOf N1fdb1b0ee04c4cb48f6c55f2432bb57f
53 Nee69e9c3ac9e41c78ed10e338ad06638
54 sg:journal.1102690
55 schema:name Effect of chiral polyhydrochromenes on cannabinoid system
56 schema:pagination 450-464
57 schema:productId N46c1473a77284900bdd189ca73364191
58 Nb722eaa967104849bf2c64b3640bf7a5
59 Ne82877daad5347b08ccf1ee2f3e8c8ff
60 schema:sameAs https://app.dimensions.ai/details/publication/pub.1111833582
61 https://doi.org/10.1007/s00044-019-02294-9
62 schema:sdDatePublished 2019-04-11T13:21
63 schema:sdLicense https://scigraph.springernature.com/explorer/license/
64 schema:sdPublisher Nee1288823178448aac1f8454e18f0c32
65 schema:url https://link.springer.com/10.1007%2Fs00044-019-02294-9
66 sgo:license sg:explorer/license/
67 sgo:sdDataset articles
68 rdf:type schema:ScholarlyArticle
69 N19ec9d8bf3ba418e895e8650a6608de6 schema:affiliation https://www.grid.ac/institutes/grid.419817.2
70 schema:familyName Nazimova
71 schema:givenName Ekaterina V.
72 rdf:type schema:Person
73 N1dcab758e5c443d38819cfd60501ef29 schema:affiliation https://www.grid.ac/institutes/grid.419817.2
74 schema:familyName Patrusheva
75 schema:givenName Oksana S.
76 rdf:type schema:Person
77 N1fdb1b0ee04c4cb48f6c55f2432bb57f schema:volumeNumber 28
78 rdf:type schema:PublicationVolume
79 N2595069a91b546f4a398e622435df5a9 rdf:first Ne3820cd9bd754223b97309d0c2aa0522
80 rdf:rest N530f5e85b3e848a8a686e59e9c185818
81 N46c1473a77284900bdd189ca73364191 schema:name doi
82 schema:value 10.1007/s00044-019-02294-9
83 rdf:type schema:PropertyValue
84 N4b23984a257b492bb58ae52e8b0be435 schema:affiliation https://www.grid.ac/institutes/grid.4605.7
85 schema:familyName Li-Zhulanov
86 schema:givenName Nikolai S.
87 rdf:type schema:Person
88 N4bb120c8e9ef48ea90b2b639d673f7f3 schema:affiliation https://www.grid.ac/institutes/grid.15447.33
89 schema:familyName Krasavin
90 schema:givenName Mikhail
91 rdf:type schema:Person
92 N4c5339aa6a6a4caea6ba103622089699 rdf:first Nf9bb9c746e9b4b46ba242a3132e46bbb
93 rdf:rest Nd6b3934dca514eeb87e12346b741ae34
94 N530f5e85b3e848a8a686e59e9c185818 rdf:first N1dcab758e5c443d38819cfd60501ef29
95 rdf:rest N8e32e4482ac44b318070713c833ec02d
96 N6669d0ff52dd4229b37807bc0e348948 schema:affiliation https://www.grid.ac/institutes/grid.419817.2
97 schema:familyName Korchagina
98 schema:givenName Dina V.
99 rdf:type schema:Person
100 N8d92ccfed5844e3da9ecc0c605a70c03 rdf:first N4b23984a257b492bb58ae52e8b0be435
101 rdf:rest Nc7f1ad95bf4f4a22b2b8d343b05e984c
102 N8e32e4482ac44b318070713c833ec02d rdf:first N19ec9d8bf3ba418e895e8650a6608de6
103 rdf:rest Nb4b88be60ae34df48b45f812fd2185df
104 Nb4b88be60ae34df48b45f812fd2185df rdf:first N6669d0ff52dd4229b37807bc0e348948
105 rdf:rest Nf2ee7379b5764bad8c7018d981d315fe
106 Nb722eaa967104849bf2c64b3640bf7a5 schema:name dimensions_id
107 schema:value pub.1111833582
108 rdf:type schema:PropertyValue
109 Nba980bcc27334d21a305a95e7ef66ed3 schema:affiliation https://www.grid.ac/institutes/grid.5734.5
110 schema:familyName Chicca
111 schema:givenName Andrea
112 rdf:type schema:Person
113 Nc51bb28fe52e4ebc9ab8430cf3100f3b schema:affiliation https://www.grid.ac/institutes/grid.4605.7
114 schema:familyName Salakhutdinov
115 schema:givenName Nariman F.
116 rdf:type schema:Person
117 Nc7f1ad95bf4f4a22b2b8d343b05e984c rdf:first Nca1b39f3838449888093a408fe9ace57
118 rdf:rest Nd77ba6cf110d408195b3c45ba1caf865
119 Nca1b39f3838449888093a408fe9ace57 schema:affiliation https://www.grid.ac/institutes/grid.4605.7
120 schema:familyName Il’ina
121 schema:givenName Irina V.
122 rdf:type schema:Person
123 Nd6b3934dca514eeb87e12346b741ae34 rdf:first Nc51bb28fe52e4ebc9ab8430cf3100f3b
124 rdf:rest rdf:nil
125 Nd77ba6cf110d408195b3c45ba1caf865 rdf:first Nba980bcc27334d21a305a95e7ef66ed3
126 rdf:rest N2595069a91b546f4a398e622435df5a9
127 Ne3820cd9bd754223b97309d0c2aa0522 schema:affiliation https://www.grid.ac/institutes/grid.5734.5
128 schema:familyName Schenker
129 schema:givenName Patricia
130 rdf:type schema:Person
131 Ne82877daad5347b08ccf1ee2f3e8c8ff schema:name readcube_id
132 schema:value 19957fc42df7aa6eb9a68dd4c72d0f121fbcb64a0cf850d4cd272e2da3dde83b
133 rdf:type schema:PropertyValue
134 Nee1288823178448aac1f8454e18f0c32 schema:name Springer Nature - SN SciGraph project
135 rdf:type schema:Organization
136 Nee69e9c3ac9e41c78ed10e338ad06638 schema:issueNumber 4
137 rdf:type schema:PublicationIssue
138 Nf2ee7379b5764bad8c7018d981d315fe rdf:first N4bb120c8e9ef48ea90b2b639d673f7f3
139 rdf:rest N4c5339aa6a6a4caea6ba103622089699
140 Nf9bb9c746e9b4b46ba242a3132e46bbb schema:affiliation https://www.grid.ac/institutes/grid.4605.7
141 schema:familyName Volcho
142 schema:givenName Konstantin P.
143 rdf:type schema:Person
144 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
145 schema:name Chemical Sciences
146 rdf:type schema:DefinedTerm
147 anzsrc-for:0305 schema:inDefinedTermSet anzsrc-for:
148 schema:name Organic Chemistry
149 rdf:type schema:DefinedTerm
150 sg:grant.4896814 http://pending.schema.org/fundedItem sg:pub.10.1007/s00044-019-02294-9
151 rdf:type schema:MonetaryGrant
152 sg:journal.1102690 schema:issn 1054-2523
153 1554-8120
154 schema:name Medicinal Chemistry Research
155 rdf:type schema:Periodical
156 sg:pub.10.1007/s00044-012-0310-9 schema:sameAs https://app.dimensions.ai/details/publication/pub.1010933253
157 https://doi.org/10.1007/s00044-012-0310-9
158 rdf:type schema:CreativeWork
159 sg:pub.10.1007/s00044-014-1071-4 schema:sameAs https://app.dimensions.ai/details/publication/pub.1031982382
160 https://doi.org/10.1007/s00044-014-1071-4
161 rdf:type schema:CreativeWork
162 sg:pub.10.1007/s00044-015-1426-5 schema:sameAs https://app.dimensions.ai/details/publication/pub.1019979354
163 https://doi.org/10.1007/s00044-015-1426-5
164 rdf:type schema:CreativeWork
165 sg:pub.10.1007/s00044-016-1573-3 schema:sameAs https://app.dimensions.ai/details/publication/pub.1000429983
166 https://doi.org/10.1007/s00044-016-1573-3
167 rdf:type schema:CreativeWork
168 sg:pub.10.1007/s10600-016-1785-2 schema:sameAs https://app.dimensions.ai/details/publication/pub.1033443662
169 https://doi.org/10.1007/s10600-016-1785-2
170 rdf:type schema:CreativeWork
171 sg:pub.10.1007/s10600-017-1966-7 schema:sameAs https://app.dimensions.ai/details/publication/pub.1084937522
172 https://doi.org/10.1007/s10600-017-1966-7
173 rdf:type schema:CreativeWork
174 sg:pub.10.1038/npp.2015.336 schema:sameAs https://app.dimensions.ai/details/publication/pub.1042379188
175 https://doi.org/10.1038/npp.2015.336
176 rdf:type schema:CreativeWork
177 https://app.dimensions.ai/details/publication/pub.1082964580 schema:CreativeWork
178 https://doi.org/10.1002/cctc.201800974 schema:sameAs https://app.dimensions.ai/details/publication/pub.1105467115
179 rdf:type schema:CreativeWork
180 https://doi.org/10.1002/hlca.200790042 schema:sameAs https://app.dimensions.ai/details/publication/pub.1022290001
181 rdf:type schema:CreativeWork
182 https://doi.org/10.1002/hlca.201000269 schema:sameAs https://app.dimensions.ai/details/publication/pub.1043172115
183 rdf:type schema:CreativeWork
184 https://doi.org/10.1016/j.bcp.2014.09.020 schema:sameAs https://app.dimensions.ai/details/publication/pub.1013542526
185 rdf:type schema:CreativeWork
186 https://doi.org/10.1016/j.bmc.2016.08.037 schema:sameAs https://app.dimensions.ai/details/publication/pub.1004572214
187 rdf:type schema:CreativeWork
188 https://doi.org/10.1016/j.carres.2013.01.012 schema:sameAs https://app.dimensions.ai/details/publication/pub.1022211704
189 rdf:type schema:CreativeWork
190 https://doi.org/10.1016/j.ejphar.2016.02.010 schema:sameAs https://app.dimensions.ai/details/publication/pub.1008053410
191 rdf:type schema:CreativeWork
192 https://doi.org/10.1016/j.mcat.2018.05.007 schema:sameAs https://app.dimensions.ai/details/publication/pub.1103944803
193 rdf:type schema:CreativeWork
194 https://doi.org/10.1016/j.molcata.2014.11.016 schema:sameAs https://app.dimensions.ai/details/publication/pub.1029650154
195 rdf:type schema:CreativeWork
196 https://doi.org/10.1016/j.molcata.2015.09.021 schema:sameAs https://app.dimensions.ai/details/publication/pub.1023981463
197 rdf:type schema:CreativeWork
198 https://doi.org/10.1016/j.molcata.2016.01.010 schema:sameAs https://app.dimensions.ai/details/publication/pub.1008512306
199 rdf:type schema:CreativeWork
200 https://doi.org/10.1016/j.neuropharm.2017.05.018 schema:sameAs https://app.dimensions.ai/details/publication/pub.1085432102
201 rdf:type schema:CreativeWork
202 https://doi.org/10.1016/j.neuropharm.2017.06.015 schema:sameAs https://app.dimensions.ai/details/publication/pub.1086043553
203 rdf:type schema:CreativeWork
204 https://doi.org/10.1016/j.tetlet.2009.02.202 schema:sameAs https://app.dimensions.ai/details/publication/pub.1034503366
205 rdf:type schema:CreativeWork
206 https://doi.org/10.1016/j.tetlet.2010.03.100 schema:sameAs https://app.dimensions.ai/details/publication/pub.1042907850
207 rdf:type schema:CreativeWork
208 https://doi.org/10.1016/j.tetlet.2018.01.040 schema:sameAs https://app.dimensions.ai/details/publication/pub.1100741724
209 rdf:type schema:CreativeWork
210 https://doi.org/10.1016/s0040-4020(01)80157-5 schema:sameAs https://app.dimensions.ai/details/publication/pub.1018680828
211 rdf:type schema:CreativeWork
212 https://doi.org/10.1021/acs.chemrev.5b00411 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055085189
213 rdf:type schema:CreativeWork
214 https://doi.org/10.1021/acs.jmedchem.7b01845 schema:sameAs https://app.dimensions.ai/details/publication/pub.1100238414
215 rdf:type schema:CreativeWork
216 https://doi.org/10.1021/jm500220s schema:sameAs https://app.dimensions.ai/details/publication/pub.1055954659
217 rdf:type schema:CreativeWork
218 https://doi.org/10.1039/c1ob00033k schema:sameAs https://app.dimensions.ai/details/publication/pub.1027000983
219 rdf:type schema:CreativeWork
220 https://doi.org/10.1055/s-0032-1316915 schema:sameAs https://app.dimensions.ai/details/publication/pub.1057266049
221 rdf:type schema:CreativeWork
222 https://doi.org/10.1070/rcr4810 schema:sameAs https://app.dimensions.ai/details/publication/pub.1104337222
223 rdf:type schema:CreativeWork
224 https://doi.org/10.1073/pnas.1704065114 schema:sameAs https://app.dimensions.ai/details/publication/pub.1085870515
225 rdf:type schema:CreativeWork
226 https://doi.org/10.1074/jbc.m112.373241 schema:sameAs https://app.dimensions.ai/details/publication/pub.1015507806
227 rdf:type schema:CreativeWork
228 https://doi.org/10.1111/bph.13887 schema:sameAs https://app.dimensions.ai/details/publication/pub.1085593650
229 rdf:type schema:CreativeWork
230 https://doi.org/10.1111/jcpt.12235 schema:sameAs https://app.dimensions.ai/details/publication/pub.1012946129
231 rdf:type schema:CreativeWork
232 https://doi.org/10.1124/jpet.108.143487 schema:sameAs https://app.dimensions.ai/details/publication/pub.1014104448
233 rdf:type schema:CreativeWork
234 https://doi.org/10.1124/jpet.112.201426 schema:sameAs https://app.dimensions.ai/details/publication/pub.1034322426
235 rdf:type schema:CreativeWork
236 https://doi.org/10.1523/jneurosci.3326-06.2006 schema:sameAs https://app.dimensions.ai/details/publication/pub.1015323262
237 rdf:type schema:CreativeWork
238 https://doi.org/10.1590/s0103-50532010000800023 schema:sameAs https://app.dimensions.ai/details/publication/pub.1018789759
239 rdf:type schema:CreativeWork
240 https://doi.org/10.2174/1570180813666161102142642 schema:sameAs https://app.dimensions.ai/details/publication/pub.1084832943
241 rdf:type schema:CreativeWork
242 https://doi.org/10.3389/fnmol.2018.00180 schema:sameAs https://app.dimensions.ai/details/publication/pub.1104260804
243 rdf:type schema:CreativeWork
244 https://doi.org/10.3762/bjoc.12.64 schema:sameAs https://app.dimensions.ai/details/publication/pub.1071380259
245 rdf:type schema:CreativeWork
246 https://www.grid.ac/institutes/grid.15447.33 schema:alternateName Saint Petersburg State University
247 schema:name Saint Petersburg State University, 199034, Saint Petersburg, Russian Federation
248 rdf:type schema:Organization
249 https://www.grid.ac/institutes/grid.419817.2 schema:alternateName Novosibirsk Institute of Organic Chemistry
250 schema:name Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation
251 rdf:type schema:Organization
252 https://www.grid.ac/institutes/grid.4605.7 schema:alternateName Novosibirsk State University
253 schema:name Novosibirsk Institute of Organic Chemistry, Lavrentjev av. 9, 630090, Novosibirsk, Russian Federation
254 Novosibirsk State University, Pirogova st. 1, 630090, Novosibirsk, Russian Federation
255 rdf:type schema:Organization
256 https://www.grid.ac/institutes/grid.5734.5 schema:alternateName University of Bern
257 schema:name Institute of Biochemistry and Molecular Medicine, NCCR TransCure, University of Bern, Bühlstrasse 28, 3012, Bern, Switzerland
258 rdf:type schema:Organization
 




Preview window. Press ESC to close (or click here)


...