Synthesis, structure and affinity of novel 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones for CNS central and peripheral benzodiazepine receptors

Andronati Sergei; Semenishyna Ekaterina; Pavlovsky Victor; Simonov Yurii A.; Makan Svetlana; Boiko Iryna; Burenkova Natalya; Gdaniec Maria; Cardinael Pascal; Bouillon Jean-Philippe; Mazepa Aleksandr

Conţinutul numărului revistei

Articolul precedent

Articolul urmator

220

SM ISO690:2012

ANDRONATI, Sergei, SEMENISHYNA, Ekaterina, PAVLOVSKY, Victor, SIMONOV, Yurii A., MAKAN, Svetlana, BOIKO, Iryna, BURENKOVA, Natalya, GDANIEC, Maria, CARDINAEL, Pascal, BOUILLON, Jean-Philippe, MAZEPA, Aleksandr. Synthesis, structure and affinity of novel 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones for CNS central and peripheral benzodiazepine receptors. In: European Journal of Medicinal Chemistry, 2010, vol. 45, pp. 1346-1351. ISSN 0223-5234. DOI: https://doi.org/10.1016/j.ejmech.2009.12.027

EXPORT metadate:
Google Scholar
Crossref
CERIF

DataCite
Dublin Core

European Journal of Medicinal Chemistry

Volumul 45 / 2010 / ISSN 0223-5234 /ISSNe 1768-3254

Synthesis, structure and affinity of novel 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones for CNS central and peripheral benzodiazepine receptors

DOI:https://doi.org/10.1016/j.ejmech.2009.12.027

Pag. 1346-1351

Andronati Sergei¹, Semenishyna Ekaterina¹, Pavlovsky Victor¹, Simonov Yurii A.², Makan Svetlana¹, Boiko Iryna¹, Burenkova Natalya¹, Gdaniec Maria³, Cardinael Pascal⁴, Bouillon Jean-Philippe⁴, Mazepa Aleksandr¹

¹ A.V. Bogatsky Physico-Chemical Institute of the NAS of Ukraine,
² Institute of Applied Physics, Academy of Sciences of Moldova,
³ Adam Mickiewicz University in Poznan,
⁴ Rouen University

Disponibil în IBN: 4 iulie 2023

Rezumat

A series of novel 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones (7-15) was synthesized and their in vitro affinity for both the central benzodiazepine receptor (CBR) and the peripheral benzodiazepine receptor (PBR) of rat brain was studied. Racemic mixture of 7-bromo-3-(2-methoxy)ethoxy-5-phenyl-1,2-dihydro-3H-1,4-benzodiazepin-2-one (13) was separated into enantiomers 14, 15 by chiral HPLC. Absolute configuration of R-enantiomer 15 was determined by the method of X-ray diffraction analysis. The affinity of S-enantiomer 14 for CBR (I{cyrillic, ukrainian}C₅₀ = 245 nM) is 20-fold higher than the affinity of R-enantiomer 15 (I{cyrillic, ukrainian}C₅₀ = 4930 nM). A high selectivity for CBR versus PBR (I{cyrillic, ukrainian}C₅₀ (PBR) > 10000 nM) was shown by all reported compounds. Compound 12 was revealed as a potent (IC₅₀ = 9 nM) and selective CBR ligand among the synthesized 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones.

Cuvinte-cheie
3-alkoxy-1, 2-dihydro-3H-1, 4-bezodiazepin-2-ones, affinity, Central benzodiazepine receptor, enantiomer, Peripheral benzodiazepine receptor, X-ray analysis

Crossref XML Export

<?xml version='1.0' encoding='utf-8'?>
<doi_batch version='4.3.7' xmlns='http://www.crossref.org/schema/4.3.7' xmlns:xsi='http://www.w3.org/2001/XMLSchema-instance' xsi:schemaLocation='http://www.crossref.org/schema/4.3.7 http://www.crossref.org/schema/deposit/crossref4.3.7.xsd'>
<head>
<doi_batch_id>ibn-184312</doi_batch_id>
<timestamp>1719249444</timestamp>
<depositor>
<depositor_name>Information Society Development Instiute, Republic of Moldova</depositor_name>
<email_address>[email protected]</email_address>
</depositor>
</head>
<body>
<journal>
<journal_metadata>
<full_title>European Journal of Medicinal Chemistry</full_title>
<issn media_type='print'>02235234</issn>
</journal_metadata>
<journal_issue>
<publication_date media_type='print'>
<year>2010</year>
</publication_date>
<issue></issue>
</journal_issue>
<journal_article publication_type='full_text'><titles>
<title>Synthesis, structure and affinity of novel 3-alkoxy-1,2-dihydro-3H-1,4-benzodiazepin-2-ones for CNS central and peripheral benzodiazepine receptors</title>
</titles>
<contributors>
<person_name sequence='first' contributor_role='author'>
<given_name>Serghei</given_name>
<surname>Andronati</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Ecaterina</given_name>
<surname>Semenişina</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Victor</given_name>
<surname>Pavlovsky</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Iurii</given_name>
<surname>Simonov</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Svetlana</given_name>
<surname>Makan</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Iryna</given_name>
<surname>Boiko</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Natalya</given_name>
<surname>Burenkova</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Maria</given_name>
<surname>Gdaniec</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Pascal</given_name>
<surname>Cardinael</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Jean-Philippe</given_name>
<surname>Bouillon</surname>
</person_name>
<person_name sequence='additional' contributor_role='author'>
<given_name>Alexandr</given_name>
<surname>Mazepa</surname>
</person_name>
</contributors>
<publication_date media_type='print'>
<year>2010</year>
</publication_date>
<pages>
<first_page>1346</first_page>
<last_page>1351</last_page>
</pages>
<doi_data>
<doi>10.1016/j.ejmech.2009.12.027</doi>
<resource>http://www.crossref.org/</resource>
</doi_data>
</journal_article>
</journal>
</body>
</doi_batch>