5-乙基尿苷 | 25110-76-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5-乙基尿苷
• 英文名称: 5-ethyluridine
• 英文别名: 5-Ethyluridin；1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethylpyrimidine-2,4-dione
• CAS: 25110-76-3
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: LNVBVDVUTCPLIZ-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C，惰性气体

制备方法与用途

5-乙基尿苷是一种嘌呤核苷类似物，具有广泛的抗肿瘤活性，尤其针对惰性淋巴系统恶性肿瘤。其抗癌机制主要通过抑制DNA合成和诱导细胞凋亡来实现。

反应信息

• 作为反应物：
  描述：

  5-乙基尿苷 在 palladium on activated charcoal 碳酸二苯酯 、 氨 、 氢气 、 sodium acetate 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 乙去氧尿啶
  参考文献：
  名称：

  5-乙基嘧啶核苷类似物的合成

  摘要：

  本文描述了5-乙基嘧啶的无环，环状和脱氧糖核苷的合成，即，i）5-乙基尿嘧啶的1-（2-羟基乙氧基甲基），1-（2-甲氧基乙氧基甲基）和1-乙氧基乙基衍生物和5-乙基胞嘧啶，ii）5-乙基-1-（四氢-2 H-吡喃-2-基）-和-1-（四氢呋喃-2-基）尿嘧啶，和iii）5-乙基-2'-脱氧尿苷。

  DOI：

  10.1002/jhet.5570340254
• 作为产物：
  描述：

  5-乙基尿嘧啶 在 三甲基氯硅烷 、 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 5-乙基尿苷
  参考文献：
  名称：

  5-Substituted UTP derivatives as P2Y2 receptor agonists

  摘要：

  A series of 5-alkyl-substituted UTP derivatives, which had been synthesized previously with a moderate degree of purity, was resynthesized, purified, and characterized. Synthetic and purification procedures were optimized. New spectroscopic data, including C-13- and P-31 NMR data, are presented. Phosphorylation reactions yielded a number of side products, such as the 2'-, 3'-, and 5'-monophosphates, the 2',3'-cyclic monophosphates, and the 2',3'-cyclic phosphates of the 5'-triphosphates. Furthermore, raw products were contaminated with inorganic phosphates, including cyclometatriphosphate, phosphate, and pyrophosphate. The uracil nucleotides were investigated for their potency to increase intracellular calcium concentrations by stimulation of P2Y(2) receptors (P2Y(2)R) on NG108-15 cells, a mouse neuroblastoma x glioma cell line, and in human basal epithelial airway cells, including a cystic fibrosis (CF/T43) cell line. UTP exhibited EC50 values of ca. 1 mu M (in NG108-15 cells) and of 0.1 mu M (in CF/T43 cells), respectively. 5-Substituted UTP derivatives were agonists at the P2Y(2)R, but were less potent than UTP. 5-Ethyl-UTP, for example, exhibited an EC50 value of 99 mu M at P2Y(2)R of NG108-15 cells and proved to be a full agonist. With increasing volume of the 5-substituent of UTP derivatives, P2Y(2) activity decreased. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00211-1

文献信息

• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• Facile Synthesis of Thymidine Derivatives by Cross-Coupling of 5-Halogenouridine Derivatives with Trimethylaluminum
  作者：Kosaku Hirota、Yukio Kitade、Yoshitake Kanbe、Yoshiaki Isobe、Yoshifumi Maki

  DOI：10.1055/s-1993-25833

  日期：——

  An efficient method for the introduction of a methyl group in the 5-position of uridine derivatives is described. This method involves three steps: protection of 5-halogenouridines 4 and 5 with hexamethyldisilazane, a palladium-catalyzed cross-coupling of the pertrimethylsilylated nucleosides with trimethylaluminum, and subsequent deprotection to afford the corresponding thymidine derivatives 6 in high overall yields.

  描述了一种在尿苷衍生物的5-位引入甲基的有效方法。该方法包括三个步骤：用六甲基二硅氮烷保护5-卤代尿苷4和5，接着通过钯催化的交叉偶联反应与全三甲基硅基化的核苷酸与三甲基铝反应，最后进行去保护，以高总收率得到相应的胸苷衍生物6。
• Use of nucleoside phosphorylases for the preparation of 5-modified pyrimidine ribonucleosides
  作者：Cyril S. Alexeev、Mikhail S. Drenichev、Evgeniya O. Dorinova、Roman S. Esipov、Irina V. Kulikova、Sergey N. Mikhailov

  DOI：10.1016/j.bbapap.2019.140292

  日期：2020.1

  from one heterocyclic base to another, is catalyzed by nucleoside phosphorylases (NPs) and is being actively developed and applied for the synthesis of biologically important nucleosides. Here, we report an efficient one-step synthesis of 5-substitited pyrimidine ribonucleosides starting from 7-methylguanosine hydroiodide in the presence of nucleoside phosphorylases (NPs).

  酶促糖基化反应，即碳水化合物部分从一个杂环碱基到另一个杂环碱基的转移，被核苷磷酸化酶（NPs）催化，正在被积极开发并用于生物学上重要的核苷的合成。在这里，我们报告有效的一步合成5取代的嘧啶核糖核苷从7-甲基鸟苷氢碘化物开始存在核苷磷酸化酶（NPs）。
• Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation
  作者：Hiromichi Tanaka、Hiroyuki Hayakawa、Kikoh Obi、Miyasaka Tadashi

  DOI：10.1016/s0040-4020(01)87642-0

  日期：1986.1

  resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described

  在尿苷的C-6位的苯硫基在2,2,6,6-四甲基哌啶锂的C-5位的锂化过程中用作保护基。所得的C-5锂化物质与各种类型的亲电试剂的反应提供了5-取代的6-苯基硫尿苷衍生物。这些产品中的苯硫基可通过新型氢化三丁基锡脱硫磺化甲锡烷基化反应，然后进行质子分解来去除。整个序列构成了5-取代的尿苷的新途径。还描述了该方法在2'-脱氧尿苷中的应用。
• Synthesis and Antiviral Activity of Acyclic Derivatives of 5-Ethyl-2′-Deoxyuridine
  作者：Klaus Keppeler、Gebhard Kiefer、Erik de Clercq

  DOI：10.1002/ardp.19863190412

  日期：——

  Four acyclic pyrimidine derivatives of 5‐ethyl‐2′‐deoxyuridine (1) (EDU) have been synthesized and tested for their activities against vesicular stomatitis virus, vaccinia virus and various strains of herpes simplex virus type 1 (HSV‐1) and herpes simplex virus type 2 (HSV‐2) in primary rabbit kidney (PRK) cell cultures. The acyclic nucleoside analogues of EDU exhibited no activity against any of the

  已经合成了 5-乙基-2'-脱氧尿苷 (1) (EDU) 的四种无环嘧啶衍生物，并测试了它们对水泡性口炎病毒、痘苗病毒和各种单纯疱疹病毒 1 型 (HSV-1) 和疱疹病毒株的活性原代兔肾 (PRK) 细胞培养物中的 2 型单纯病毒 (HSV-2)。EDU 的无环核苷类似物对任何测试的病毒都没有表现出活性。