Mibu Nobuko, Yokomizo Kazumi, Miyata Takeshi, Sumoto Kunihiro
Faculty of Pharmaceutical Sciences, Fukuoka University, Fukuoka, Japan.
Chem Pharm Bull (Tokyo). 2007 Sep;55(9):1406-11. doi: 10.1248/cpb.55.1406.
Some new N-monocarbamoyl symmetrical diamines have been prepared by the addition of symmetrical amines to isocyanates or isothiocyanates. 2,6-Diaminopyridine (1), (1R,2R)-1,2-diaminocyclohexane [(1R,2R)-2], meso-1,2-diaminocyclohexane (meso-2), or (1R,2R)-1,2-diphenylethylenediamine (3) were used as the starting symmetrical diamine frameworks. All of the newly synthesized compounds were subjected to an evaluation of antiviral activity with herpes simplex virus (HSV)-1. N-Monocarbamoyl 2,6-diaminopyridines (5a, b) showed significant antiviral activity (EC(50)=17.0, 6.2 microg/ml) comparable to that of N-monododecanoyl 2,6-diaminopyridine (A2). As a result, compound 5a showed a better selectivity index (CC(50)/EC(50) = ca. 10.0) than that of A2.
通过将对称胺添加到异氰酸酯或异硫氰酸酯中，制备了一些新型的N-单氨基甲酰基对称二胺。以2,6-二氨基吡啶（1）、（1R,2R）-1,2-二氨基环己烷[（1R,2R）-2]、内消旋-1,2-二氨基环己烷（内消旋-2）或（1R,2R）-1,2-二苯基乙二胺（3）作为起始的对称二胺骨架。所有新合成的化合物均针对单纯疱疹病毒（HSV）-1进行了抗病毒活性评估。N-单氨基甲酰基2,6-二氨基吡啶（5a、b）表现出显著的抗病毒活性（EC50 = 17.0、6.2微克/毫升），与N-单十二烷酰基2,6-二氨基吡啶（A2）相当。结果，化合物5a的选择性指数（CC50/EC50约为10.0）优于A2。
