Investigating the effects of the core nitrogen atom configuration on the thermodynamic solubility of 6,​5-​bicyclic heterocycles

Cosgrove, Brett and Down, Kenneth and Bertrand, Sophie and Tomkinson, Nicholas C.O. and Barker, Michael D. (2021) Investigating the effects of the core nitrogen atom configuration on the thermodynamic solubility of 6,​5-​bicyclic heterocycles. Bioorganic and Medicinal Chemistry Letters, 33. 127752. ISSN 0960-894X (https://doi.org/10.1016/j.bmcl.2020.127752)

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Abstract

Physicochemical properties, such as solubility, are important when prioritising compounds for progression on a drug discovery project. There is limited literature around the systematic effects of core changes on thermodynamic solubility. This work details the synthesis of nitrogen containing 6,5-bicyclic heterocyclic cores which are common scaffolds in medicinal chemistry and the analysis of their physicochemical properties, particularly, thermodynamic solubility. Crystalline solids were obtained where possible to enable a robust comparison of the thermodynamic solubility. Other parameters such as pKa, melting point and lipophilicity were also measured to determine the key factors affecting the observed solubility.

ORCID iDs

Cosgrove, Brett, Down, Kenneth, Bertrand, Sophie, Tomkinson, Nicholas C.O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133 and Barker, Michael D.;
  • Item type:Article
    ID code:76856
    Dates:
    Date
    Event
    1 February 2021
    Published
    29 December 2020
    Published Online
    13 December 2020
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:22 Jun 2021 10:46
    Last modified:11 Nov 2024 13:08
    URI:https://strathprints.strath.ac.uk/id/eprint/76856
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