Secrist J A, Shortnacy A T, Montgomery J A
Kettering-Meyer Laboratory, Southern Research Institute, Birmingham, Alabama 35255-5305.
J Med Chem. 1988 Feb;31(2):405-10. doi: 10.1021/jm00397a024.
The synthesis of a series of 2-chloro- or 2-fluoro-9-(2-substituted-2-deoxy-beta-D-arabinofuranosyl)adenines (4g-n) is described. New compounds were prepared from either 2-chloroadenosine or 2-fluoroadenosine by first blocking the 3'- and 5'-hydroxyls as the tetraisopropyldisiloxane derivatives. Activation of O-2' by formation of a triflate followed by nucleophilic displacement allowed introduction of various groups in the proper configuration at C-2'. Fluoride ion treatment then produced the deblocked nucleosides. All of the new compounds were evaluated as cytotoxic agents against L1210 and H.Ep.-2 cells and as antiviral agents against herpes simplex viruses 1 and 2 and vaccinia virus in culture.
本文描述了一系列2-氯-或2-氟-9-(2-取代-2-脱氧-β-D-阿拉伯呋喃糖基)腺嘌呤(4g-n)的合成。新化合物由2-氯腺苷或2-氟腺苷制备，首先将3'-和5'-羟基封闭为四异丙基二硅氧烷衍生物。通过形成三氟甲磺酸酯活化O-2'，随后进行亲核取代，从而在C-2'处以适当构型引入各种基团。然后用氟离子处理得到脱保护的核苷。所有新化合物均作为细胞毒性剂针对L1210和H.Ep.-2细胞进行了评估，并作为抗病毒剂针对培养中的单纯疱疹病毒1型和2型以及痘苗病毒进行了评估。
