Uses
(3-Carboxypropyl)triphenylphosphonium bromide is used as antimalarial agents, antimycobacterial agents,antifungal agents, inhibitors of protein tyrosine phosphatase.
Uses
(3-Carboxypropyl)triphenylphosphonium Bromide is a reagent used in the preparation of sphingosine 1-phosphate-1 receptor antagonists. Also used in the synthesis of mitochondrial vitamin E metabolites and other mitochondrial targets in the study of mitochodrial functions. Also used in the preparation of benzosuberene analogs that inhibit tubulin assembly and demonstrate cytotoxicity.
Synthesis
General procedure: 4-Bromobutyric acid (1 eq.) and triphenylphosphine (1 eq.) were dissolved in 300 mL of toluene under argon protection and heated to reflux for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. The target product (3-propylcarboxy)triphenylphosphonium bromide was obtained by crystallization and purification of the residue from a suitable solvent.
References
[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5088 - 5102
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2002, vol. 57, # 3, p. 335 - 337
[4] Tetrahedron Letters, 2016, vol. 57, # 10, p. 1083 - 1086
[5] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5805 - 5813
