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Review Article

4-硫代呋喃酸烯糖：选择性合成4-硫代核苷β-异构体的多功能糖基供体及其生物活性

卷 29, 期 21, 2022

发表于: 20 January, 2022

页: [3684 - 3731] 页: 48

弟呕挨: 10.2174/0929867328666211115121434

价格: $65

摘要

利用3,5-O-（二叔丁基硅基）（DTBS）-4-硫代呋喃酸糖醛作为糖基供体，通过亲电糖苷化，首次高度非对映选择性地合成了4-硫代核苷的β-异构体。所得到的糖苷通过2-取代基的化学转化转化为核糖、2-脱氧和阿拉伯呋喃酰基核苷。糖醛氧化物的加性Pummer反应生成1,2-二-O-乙酰基-3,5-O-DTBS-4-硫代呋喃核糖。通过基于Vorbruggen糖苷化制备嘧啶和嘌呤-4-硫代核糖核苷的4-硫代类似物，证明了DTB保护的4-硫代呋喃核糖的效用。还进行了C-核苷抗生素噻唑呋喃的4-硫对应物的合成。通过1-三丁基烷基糖醛的交叉偶联获得的1-C-芳基或1-C-杂芳基糖醛的α-面选择性硼氢化反应提供了4-硫代-C-核糖核苷的相应β-异构体，包括核苷抗生素假尿苷和9-脱氮腺苷的4-硫代类似物。在锂化化学的基础上，合成了1-C-和2-C-碳取代的3,5-O-（1,1,3,3-四异丙基二硅氧烷-1,3-二基）（TIPDS）-4-硫代呋喃酸糖醛。这些糖醛使我们能够制备1_C-和2_β-C-碳取代的2_脱氧-4_硫核苷，包括抗肿瘤核苷抗生狭霉素C的硫对应物。此外，1_C-甲基-4_硫胸苷是一种有效的血管生成抑制剂。此外，1¬_C-甲基-4_-硫代胸苷对疱疹病毒胸苷激酶缺陷突变体的抑制活性比更昔洛韦更强。在4-取代的4-硫代胸腺嘧啶中，4-氰基和4-乙炔基衍生物抑制抗3TC（HIVM184V）的HIV变体复制的能力与HIV-1IIB一样强。就选择性指数（SI）而言，4_C-氰基-4_ -硫代胸苷的选择性指数（SI）是相应胸苷衍生物的3倍。此外，4'-C-乙炔基-2'-脱氧-4'-硫鸟嘌呤核苷酸的值是2'-脱氧鸟苷对应物（933）的20倍（>18200）。此外，4-叠氮-4-硫代胸苷是一种选择性和有效的抗EBV药物。在抗肿瘤活性方面，4-叠氮基和4-氟甲基-2-脱氧-4-硫胞苷抑制人B细胞（CCRF-SB）和T细胞白血病（Molt-4）细胞系的增殖，尽管母体化合物2-脱氧-4-硫胞苷在100μM以下没有表现出任何细胞毒性。这些有关生物活性的事实表明，用硫原子取代呋喃糖氧是开发低毒抗病毒和抗肿瘤核苷抗代谢药物的一种有希望的方法。4-硫核苷还作为寡核苷酸（ONs）治疗剂的单体，具有优异的生物学特性。因此，本综述为反义ON和siRNA提供了广泛的潜在单体。

关键词: 核苷、硫代糖、糖醛、糖苷化、抗肿瘤活性、抗病毒活性。

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