Pharmaceutical Applications
α-(p-Aminophenyl)butyric acid can be used as a ligand for the development of
GABA receptor modulators, which are crucial in the treatment of
neurological disorders. Its structural similarity to GABA allows it to
interact with GABA receptors, potentially modulating their activity and
offering therapeutic benefits.
Synthesis
2-(4-Nitrophenyl)butyric acid (10.0 g, 47.8 mmol) and carbon-loaded palladium catalyst (0.25 g) were suspended in methanol (100 mL). The reaction mixture was stirred overnight at room temperature and 1 atm hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the diatomaceous earth was washed with methanol (50 mL). The filtrates were combined and concentrated using a rotary evaporator. Water (200 mL) was added to the concentrate and recrystallized. The mixture was cooled in an ice bath to precipitate a pink solid product. The solid was collected by vacuum filtration and dried under vacuum to give 5.8 g of 2-(4-aminophenyl)butyric acid in 68% yield. The product was characterized by the following data: NMR (400 MHz, DMSO-d6) δ 11.88 (s, 1H, COOH), 6.73 (d, J = 8.4 Hz, 2H, ArH), 6.31 (d, J = 8.4 Hz, 2H, ArH), 4.77 (s, 2H, NH2), 2.98 (t, J = 7.5 Hz, 1H, CH). 1.68 (m, 1H, CH2), 1.39 (m, 1H, CH2), 0.62 (t, J = 7.3 Hz, 3H, CH3); MS (ESI) m/z 202.1 ([M+Na]+).
References
[1] Patent: WO2017/205451, 2017, A1. Location in patent: Paragraph 0293
[2] Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 451
[3] Patent: US5214191, 1993, A
[4] Patent: CN106631974, 2017, A. Location in patent: Paragraph 0028; 0029; 0031; 0032; 0033
