The Journal of Organic Chemistry · 2021 · 31 citations · 25 references
PharmacyChemistryMedicinal ChemistryOrganic ChemistryStructure-activity RelationshipsSynthetic Medicinal ChemistryHeterocyclic ChemistryLipophilicity ModulationAntihypertensive Drug TherapyAntihypertensive PharmacologyChemical Synthesis Of AnaloguesHeterocyclic Medicinal ChemistryLipophilicity ModificationMedicinal Chemistry ApplicationsMedicinal Heterocycles
A general practical approach to hetero(aromatic) and aliphatic P(O)Me2-substituted derivatives is elaborated. The key synthetic step was a [Pd]-mediated C–P coupling of (hetero)aryl bromides/iodides with HP(O)Me2. The P(O)Me2 substituent was shown to dramatically increase solubility and decrease lipophilicity of organic compounds. This tactic was used to improve the solubility of the antihypertensive drug prazosin without affecting its biological profile.
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