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Title: Synthesis of 1,2,3-triazole derivatives and their evaluation as potential CB1 receptor ligands

Author:

Szafrański, Przemysław

Date:

2017

Type:

Praca doktorska

Abstract:

The endocannabinoid system, which includes the CB1 receptors, is an interesting research subject due to its physiological roles and therapeutic applications. The aim of this thesis was to synthesize a library of potential CB1 receptor ligands and evaluate their biological activity and physicochemical properties. The library was designed to investigate the validity of the non-classical cannabinoid pharmacophore model for bicyclic 1,2,3-triazole derivatives. The choice of 1,2,3-triazole as a core unit use of the click chemistry concept, presented by Sharpless in 2001. The performed research allowed to synthesize 30 of novel 1,2,3-triazole derivatives and investigate their structure, CB1 receptor affinity, and lipophilicity. These studies revealed JCC2-65 as a micromolar CB1 receptor antagonist and provided important indications concerning structure-activity relationships within this class of compounds. JCC1-45 as a model compound for chemical stability and metabolism studies, proved to be chemically stable under a variety of conditions, but it also was very easily metabolized by Cunninghamella microorganisms. The synthetic studies also allowed to discover AMTC as a water-soluble chelate ligand improving the yield of copper-catalyzed azide-alkyne cycloaddition and to develop efficient and reliable synthetic protocols using AMTC.

Place of publishing:

Kraków

Level of degree:

2 - studia doktoranckie

Degree discipline:

farmacja ; chemia

Degree grantor:

Jagiellonian University Medical College. Faculty of Pharmacy. Chair of Organic Chemistry. Department of Organic Chemistry.

Promoter:

Marek Cegła

Date issued:

2016

Format:

application/pdf

Identifier:

oai:dl.cm-uj.krakow.pl:4248

Call number:

ZB-126489

ControlNumberVIRTUA:

click here to follow the link

Language:

eng

Access rights:

tylko w bibliotece

Location of original object:

Biblioteka Medyczna Uniwersytetu Jagiellońskiego- Collegium Medicum

Subject and keywords:

Cannabinoids CB1 receptor 1,2,3-triazole cycloaddition click chemistry

Object collections:

Last modified:

May 24, 2021

In our library since:

Aug 28, 2018

Number of object content hits:

26

Number of object content views in PDF format

9

All available object's versions:

http://dl.cm-uj.krakow.pl:8080/publication/4249

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Edition name Date
ZB-126489 May 24, 2021

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