Synthesis and Optical Resolution of 2-Aryl-2-fluoropropionic Acids, Fluorinated Analogues of Non-steroidal Anti-inflammatory Drugs (NSAIDs)

• Published in: Chemical & pharmaceutical bulletin Vol. 53; no. 5; pp. 524 - 528
• Main Authors: Fujisawa, Hidehito, Fujiwara, Tomoya, Takeuchi, Yoshio, Omata, Kenji
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.05.2005; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: 2-aryl-2-fluoropropionic acid; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; isostere; Life Sciences & Biomedicine; Molecular Conformation; non-steroidal anti-inflammatory drug; Optical Rotation; perchloryl fluoride; Pharmacology & Pharmacy; Physical Sciences; Propionates - chemical synthesis; Propranolol - analogs & derivatives; Propranolol - chemical synthesis; Science & Technology; α-fluorination; alpha-fluorination; perchloryl fluoride; 2-aryl-2-fluoropropionic acid; METABOLIC CHIRAL INVERSION; ESTERS; CONSEQUENCES; 2-PHENYLPROPIONIC ACID; 2-ARYLPROPIONIC ACIDS; isostere; non-steroidal anti-inflammatory drug
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.53.524

We report the synthesis of optically active 2-aryl-2-fluoropropionic acids 2 as non-epimerizable mimics of 2-arylpropionic acids 1, a class of compounds which have been widely used as non-steroidal anti-inflammatory drugs (NSAIDs). This is a continuation of our research involving the design, synthesis, and evaluation of chiral fluorine-containing organic molecules as effective analogues of pharmacologically important compounds.