Bolli, Martin H. published the artcileNovel S1P1 Receptor Agonists – Part 3: From Thiophenes to Pyridines, Application In Synthesis of 57044-25-4, the publication is Journal of Medicinal Chemistry (2014), 57(1), 110-130, database is CAplus and MEDLINE.
In preceding communications the authors summarized the authors’ medicinal chem. efforts leading to the identification of thiophene derivatives acting as potent, selective, and orally active S1P1 agonists. As a continuation of these efforts, the authors replaced the thiophene by a 2-, 3-, or 4-pyridine and obtained less lipophilic, potent, and selective S1P1 agonists (e.g., efficiently reducing blood lymphocyte count in the rat). Structural features influencing the compounds’ receptor affinity profile and pharmacokinetics are discussed. In addition, the ability to penetrate brain tissue has been studied for several compounds As a typical example for these pyridine based S1P1 agonists, N-((S)-3-{4-[5-(2-Diethylamino-6-methylpyridin4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide showed EC50 values of 0.6 and 352 nM for the S1P1 and S1P3 receptor, resp., displayed favorable PK properties, and penetrated well into brain tissue. In the rat, N-((S)-3-{4-[5-(2-Diethylamino-6-methylpyridin4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide maximally reduced the blood lymphocyte count for at least 24 h after oral dosing of 3 mg/kg.
Journal of Medicinal Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application In Synthesis of 57044-25-4.
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