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New spirohydantoin derivatives : synthesis, pharmacological evaluation and molecular modeling study

2016
journal article
article
Journal
Acta Poloniae Pharmaceutica. Drug Research
15
Author
Czopek Anna

Zagórska Agnieszka

Kołaczkowski Marcin

Bucki Adam

Gryzło Beata
Show more
Volume
73
Number
6
Pages
1545-1554
ISSN
0001-6837
eISSN
2353-5288
Keywords in English

imidazolidine-2,4-dione

long-chain arylpiperazines

multi-receptor ligands

spirohydantoin

URL
https://www.ptfarm.pl/download/?file=File%2FActa_Poloniae%2F2016%2F6%2F1545.pdf
Access date
2020-07-24
Remarks

Bibliogr. s. 1554

Language
English
Journal language
English
Abstract in English

A series of new arylpiperazinylpropyl derivatives of 8/6-phenyl-1,3-diazaspiro[4.5]decan-2,4-dione and spiro[imidazolidine-4,1í-indene/naphthalene]-2,5-dione was synthesized and their affinity was evaluated toward serotonin 5-HT1A, 5-HT2A, 5-HT7 receptors, dopaminergic D2, D3 receptors, adrenergic α1 receptors, and serotonin transporter (SERT). The highest affinity for serotonin 5-HT1A/2A/7 receptors was found for compounds containing a tetralin or indane moiety in the imide part. Among these, two compounds (19, 20) were selected for further pharmacological in vivo studies. A binding mode of representative molecule 19, which behaved as a 5-HT1A agonist and weak 5-HT7 antagonist in the site of 5-HT1A/7, was also analyzed in computationa studies. Moreover, two highly selective (9 and 11) 5-HT2A receptor antagonists were obtained.

Affiliation
Wydział Farmaceutyczny : Zakład Chemii LekówWydział Farmaceutyczny : Zakład Chemii OrganicznejWydział Farmaceutyczny : Zakład FarmakodynamikiWydział Farmaceutyczny : Katedra Farmakobiologii
dc.abstract.enA series of new arylpiperazinylpropyl derivatives of 8/6-phenyl-1,3-diazaspiro[4.5]decan-2,4-dione and spiro[imidazolidine-4,1í-indene/naphthalene]-2,5-dione was synthesized and their affinity was evaluated toward serotonin 5-HT1A, 5-HT2A, 5-HT7 receptors, dopaminergic D2, D3 receptors, adrenergic α1 receptors, and serotonin transporter (SERT). The highest affinity for serotonin 5-HT1A/2A/7 receptors was found for compounds containing a tetralin or indane moiety in the imide part. Among these, two compounds (19, 20) were selected for further pharmacological in vivo studies. A binding mode of representative molecule 19, which behaved as a 5-HT1A agonist and weak 5-HT7 antagonist in the site of 5-HT1A/7, was also analyzed in computationa studies. Moreover, two highly selective (9 and 11) 5-HT2A receptor antagonists were obtained.pl
dc.affiliationWydział Farmaceutyczny : Zakład Chemii Lekówpl
dc.affiliationWydział Farmaceutyczny : Zakład Chemii Organicznejpl
dc.affiliationWydział Farmaceutyczny : Zakład Farmakodynamikipl
dc.affiliationWydział Farmaceutyczny : Katedra Farmakobiologiipl
dc.cm.date2020-01-07
dc.cm.id79534
dc.contributor.authorCzopek, Anna - 129115 pl
dc.contributor.authorZagórska, Agnieszka - 133872 pl
dc.contributor.authorKołaczkowski, Marcin - 130216 pl
dc.contributor.authorBucki, Adam - 140601 pl
dc.contributor.authorGryzło, Beata - 107723 pl
dc.contributor.authorRychtyk, Joanna - 166109 pl
dc.contributor.authorPawłowski, Maciej - 133112 pl
dc.contributor.authorSiwek, Agata - 133399 pl
dc.contributor.authorSatała, Grzegorzpl
dc.contributor.authorBojarski, Andrzej J.pl
dc.contributor.authorKubacka, Monika - 130496 pl
dc.contributor.authorFilipek, Barbara - 129364 pl
dc.date.accession2020-07-24pl
dc.date.accessioned2020-01-17T09:10:34Z
dc.date.available2020-01-17T09:10:34Z
dc.date.issued2016pl
dc.date.openaccess0
dc.description.accesstimew momencie opublikowania
dc.description.additionalBibliogr. s. 1554pl
dc.description.number6pl
dc.description.physical1545-1554pl
dc.description.points15pl
dc.description.versionostateczna wersja wydawcy
dc.description.volume73pl
dc.identifier.eissn2353-5288pl
dc.identifier.issn0001-6837pl
dc.identifier.projectROD UJ / OPpl
dc.identifier.urihttps://ruj.uj.edu.pl/xmlui/handle/item/138941
dc.identifier.weblinkhttps://www.ptfarm.pl/download/?file=File%2FActa_Poloniae%2F2016%2F6%2F1545.pdfpl
dc.languageengpl
dc.language.containerengpl
dc.rightsUdzielam licencji. Uznanie autorstwa - Użycie niekomercyjne 4.0 Międzynarodowa*
dc.rights.licenceCC-BY-NC
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/legalcode.pl*
dc.share.typeotwarte czasopismo
dc.subject.enimidazolidine-2,4-dionepl
dc.subject.enlong-chain arylpiperazinespl
dc.subject.enmulti-receptor ligandspl
dc.subject.enspirohydantoinpl
dc.subtypeArticlepl
dc.titleNew spirohydantoin derivatives : synthesis, pharmacological evaluation and molecular modeling studypl
dc.title.journalActa Poloniae Pharmaceutica. Drug Researchpl
dc.typeJournalArticlepl
dspace.entity.typePublication
dc.abstract.enpl
A series of new arylpiperazinylpropyl derivatives of 8/6-phenyl-1,3-diazaspiro[4.5]decan-2,4-dione and spiro[imidazolidine-4,1í-indene/naphthalene]-2,5-dione was synthesized and their affinity was evaluated toward serotonin 5-HT1A, 5-HT2A, 5-HT7 receptors, dopaminergic D2, D3 receptors, adrenergic α1 receptors, and serotonin transporter (SERT). The highest affinity for serotonin 5-HT1A/2A/7 receptors was found for compounds containing a tetralin or indane moiety in the imide part. Among these, two compounds (19, 20) were selected for further pharmacological in vivo studies. A binding mode of representative molecule 19, which behaved as a 5-HT1A agonist and weak 5-HT7 antagonist in the site of 5-HT1A/7, was also analyzed in computationa studies. Moreover, two highly selective (9 and 11) 5-HT2A receptor antagonists were obtained.
dc.affiliationpl
Wydział Farmaceutyczny : Zakład Chemii Leków
dc.affiliationpl
Wydział Farmaceutyczny : Zakład Chemii Organicznej
dc.affiliationpl
Wydział Farmaceutyczny : Zakład Farmakodynamiki
dc.affiliationpl
Wydział Farmaceutyczny : Katedra Farmakobiologii
dc.cm.date
2020-01-07
dc.cm.id
79534
dc.contributor.authorpl
Czopek, Anna - 129115
dc.contributor.authorpl
Zagórska, Agnieszka - 133872
dc.contributor.authorpl
Kołaczkowski, Marcin - 130216
dc.contributor.authorpl
Bucki, Adam - 140601
dc.contributor.authorpl
Gryzło, Beata - 107723
dc.contributor.authorpl
Rychtyk, Joanna - 166109
dc.contributor.authorpl
Pawłowski, Maciej - 133112
dc.contributor.authorpl
Siwek, Agata - 133399
dc.contributor.authorpl
Satała, Grzegorz
dc.contributor.authorpl
Bojarski, Andrzej J.
dc.contributor.authorpl
Kubacka, Monika - 130496
dc.contributor.authorpl
Filipek, Barbara - 129364
dc.date.accessionpl
2020-07-24
dc.date.accessioned
2020-01-17T09:10:34Z
dc.date.available
2020-01-17T09:10:34Z
dc.date.issuedpl
2016
dc.date.openaccess
0
dc.description.accesstime
w momencie opublikowania
dc.description.additionalpl
Bibliogr. s. 1554
dc.description.numberpl
6
dc.description.physicalpl
1545-1554
dc.description.pointspl
15
dc.description.version
ostateczna wersja wydawcy
dc.description.volumepl
73
dc.identifier.eissnpl
2353-5288
dc.identifier.issnpl
0001-6837
dc.identifier.projectpl
ROD UJ / OP
dc.identifier.uri
https://ruj.uj.edu.pl/xmlui/handle/item/138941
dc.identifier.weblinkpl
https://www.ptfarm.pl/download/?file=File%2FActa_Poloniae%2F2016%2F6%2F1545.pdf
dc.languagepl
eng
dc.language.containerpl
eng
dc.rights*
Udzielam licencji. Uznanie autorstwa - Użycie niekomercyjne 4.0 Międzynarodowa
dc.rights.licence
CC-BY-NC
dc.rights.uri*
http://creativecommons.org/licenses/by-nc/4.0/legalcode.pl
dc.share.type
otwarte czasopismo
dc.subject.enpl
imidazolidine-2,4-dione
dc.subject.enpl
long-chain arylpiperazines
dc.subject.enpl
multi-receptor ligands
dc.subject.enpl
spirohydantoin
dc.subtypepl
Article
dc.titlepl
New spirohydantoin derivatives : synthesis, pharmacological evaluation and molecular modeling study
dc.title.journalpl
Acta Poloniae Pharmaceutica. Drug Research
dc.typepl
JournalArticle
dspace.entity.type
Publication
Affiliations
Wydział Farmaceutyczny
Czopek, Anna
Zagórska, Agnieszka
Kołaczkowski, Marcin
Bucki, Adam
Gryzło, Beata
Rychtyk, Joanna
Pawłowski, Maciej
Siwek, Agata
Kubacka, Monika
Filipek, Barbara
No affiliation
Satała, Grzegorz
Bojarski, Andrzej J.

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