McCord T J, Watson R N, DuBose C E, Hulme K L, Davis A L
J Med Chem. 1976 Mar;19(3):429-30. doi: 10.1021/jm00225a020.
beta-(1-Chloro-2-naphthyl)alanine and beta-(1-bromo-2-naphthyl) alanine were synthesized by ammonolysis of the corresponding alpha, 1-dihalo-2-naphthalenepropanoic acids derived from 1-nitro-2-naphthylamine by diazotization and condensation with acrylic acid in the presence of cuprous halides. The two analogs as well as the previously reported beta-(2-naphthyl)alanine and beta-(1-naphthyl)alanine were studied as growth inhibitors of Escherichia coli 9723, Leuconostoc dextranicum 8086, and Lactobacillus plantarum 8014. In general, the chloro and bromo analogs were more effective than the unsubstituted naphthylalanines as growth inhibitors of the three microorganisms studied.
β-(1-氯-2-萘基)丙氨酸和β-(1-溴-2-萘基)丙氨酸是通过对相应的α,1-二卤-2-萘基丙酸进行氨解反应合成的，这些α,1-二卤-2-萘基丙酸由1-硝基-2-萘胺经重氮化反应制得，并在卤化亚铜存在下与丙烯酸缩合。对这两种类似物以及先前报道的β-(2-萘基)丙氨酸和β-(1-萘基)丙氨酸作为大肠杆菌9723、右旋糖明串珠菌8086和植物乳杆菌8014生长抑制剂进行了研究。总体而言，在所研究的三种微生物中，氯代和溴代类似物作为生长抑制剂比未取代的萘基丙氨酸更有效。
