Alkylation and aralkylation of cytosine at the 1-position
Alkylation and aralkylation of cytosine at the 1-position
复制标题
1 位胞嘧啶的烷基化和芳烷基化
DOI：
10.1021/jo00336a042
复制
发表时间：
1981
影响因子：
2.4
通讯作者：
D. Helfer
中科院分区：
文献类型：
--
作者：
D. Helfer
我们对1-取代胞嘧啶的兴趣源于这些化合物的一系列有趣的性质，例如它们作为脱氧胞苷激酶抑制剂的能力，与9-取代鸟嘌呤的1，2互补碱基配对，3，4嘧啶碱基间堆积和不对称碱基间氢键，5肽基转移酶活性，6和光谱检测的限制性旋转的双核氨基功能，更重要的是，用作许多高度可溶的、短效的、有效的抗菌剂的前体，例如磺胞苷（即，1-乙基/4-磺胺基胞嘧啶）。我们对胞嘧啶的1-烷基化的经验加上除了定制订单之外缺乏1-烷基胞嘧啶的可用性，导致我们寻求在胞嘧啶的1-位烷基化和芳烷基化的更好和更方便的方法。已发表的1-取代胞嘧啶的合成方法存在许多问题-产率低、多产物、多步骤序列和/或异构体分离：（a）胞嘧啶的直接烷基化，
Our interest in 1-substituted cytosinesstems from a spectrum of intriguing properties of these compounds such as their ability to serve as inhibitors of deoxycytidine kinase, 1, 2 complementary base pairing with a 9-substituted guanine, 3, 4 interpyrimidine base stacking and asymmetric interbase hydrogen bonding, 5 peptidyl transferase activity, 6 and spectroscopic detection of restricted rotation of the extranuclear amino function, 7 and, more importantly, to serve as precursors to many highly soluble, short-acting, potent antibacterials such as sulfacytine (ie, 1-ethyllV4-sulfanilylcytosine), 8Our experience with 1-alkylation of cytosine9™ 1 11 coupled with the lack of availability of 1-alkylcytosines except by custom order led us to seek a better and more convenient approach to alkylation and aralkylation at the 1-position of cytosine. The published procedures for the synthesis of 1-sub-stituted cytosines sufferfrom a variety of problems—poor yields, multiple products, multi-step sequences, and/or isomer separation:(a) direct alkylation of cytosine em-