Azzolina Ornella, Collina Simona, Urbano Mariangela, Fata Emilio, Loddo Guya, Linati Laura, Lanza Enrica, Barbieri Annalisa
Dipartimento di Chimica Farmaceutica, Università di Pavia, Viale Taramelli 12, I-27100, Pavia, Italy.
Chirality. 2006 Nov;18(10):841-8. doi: 10.1002/chir.20328.
The diastereoselective synthesis via Grignard reaction of enantiopure analgesic naphthylaminoalcohols has been performed. The chiral racemic key intermediate 3-dimethylamino-2-methyl-1-(naphthalen-2-yl)propan-1-one and enantiomers were prepared and transformed into the desired compounds by addition of the organometallic reagent. The chemical characterization of all diastereoisomers was accomplished by 1H NMR and HPLC analyses and the absolute configuration assigned by CD spectroscopy. The in vitro and in vivo profile has also been evaluated.
通过格氏反应实现了对映体纯的镇痛萘基氨基醇的非对映选择性合成。制备了手性外消旋关键中间体3-二甲基氨基-2-甲基-1-(萘-2-基)丙-1-酮及其对映体，并通过添加有机金属试剂将其转化为所需化合物。通过1H NMR和HPLC分析完成了所有非对映异构体的化学表征，并通过圆二色光谱确定了绝对构型。还评估了其体外和体内特性。
