Mian A M, Long R A, Allen L B, Sidwell R W, Robins R K, Khwaja T A
J Med Chem. 1979 May;22(5):514-8. doi: 10.1021/jm00191a011.
1-beta-D-Arabinofuranosyl-2-amino-1,4(2H)-imino-5-fluoropyrimidine (10), 1-beta-D-arabinofuranosyl-2-amino-1,4(2H)-imino-5-fluoropyrimidine 3'-phosphate (9), and 1-beta-D-arabinofuranosyl-2-amino-1,4(2H)-imino-5-chloropyrimidine (11) have been synthesized from 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine (5), 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-fluorocytosine 3'-phosphate (4), and 2,2'-anhydro-1-beta-D-arabinofuranosyl-5-chlorocytosine (6), respectively. 2,2'-Anhydro-1-beta-D-arabinofuranosylcytosine 3'-phosphate (7), 1-beta-D-arabinofuranosyl-2-amino-1,4-(2H)-iminopyrimidine (13), 1-beta-D-arabinofuranosyl-2-amino-1,3(2H)-iminopyrimidine 3'-phosphate (12), and compounds 4, 5, and 9 showed significant in vitro activity against a number of DNA viruses. Compounds 7 and 12 were also effective in vivo against type 1 herpes simplex virus. Compounds 7, 12, and 13 were extremely effective in the treatment of mice bearing leukemia L1210.
1-β-D-阿拉伯呋喃糖基-2-氨基-1,4(2H)-亚氨基-5-氟嘧啶（10）、1-β-D-阿拉伯呋喃糖基-2-氨基-1,4(2H)-亚氨基-5-氟嘧啶3'-磷酸酯（9）和1-β-D-阿拉伯呋喃糖基-2-氨基-1,4(2H)-亚氨基-5-氯嘧啶（11）分别由2,2'-脱水-1-β-D-阿拉伯呋喃糖基-5-氟胞嘧啶（5）、2,2'-脱水-1-β-D-阿拉伯呋喃糖基-5-氟胞嘧啶3'-磷酸酯（4）和2,2'-脱水-1-β-D-阿拉伯呋喃糖基-5-氯胞嘧啶（6）合成。2,2'-脱水-1-β-D-阿拉伯呋喃糖基胞嘧啶3'-磷酸酯（7）、1-β-D-阿拉伯呋喃糖基-2-氨基-1,4-(2H)-亚氨基嘧啶（13）、1-β-D-阿拉伯呋喃糖基-2-氨基-1,3(2H)-亚氨基嘧啶3'-磷酸酯（12）以及化合物4、5和9对多种DNA病毒显示出显著的体外活性。化合物7和12对1型单纯疱疹病毒在体内也有效。化合物7、12和13在治疗携带白血病L1210的小鼠方面极其有效。
