β-5-(2-thienyl)-2'-deoxy-3',5'-di-O-acetyluridine | 133787-21-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: β-5-(2-thienyl)-2'-deoxy-3',5'-di-O-acetyluridine
• 英文别名: 3',5'-di-O-acetyl-5-thien-2-yl-2'-deoxyuridine；[(2R,3S,5R)-3-acetyloxy-5-(2,4-dioxo-5-thiophen-2-ylpyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 133787-21-0
• 化学式: C₁₇H₁₈N₂O₇S
• 分子量: 394.405
• InChiKey: JEFRCYADVNYCPT-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  β-5-(2-thienyl)-2'-deoxy-3',5'-di-O-acetyluridine 在 ammonium cerium(IV) nitrate 、 氢碘酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 5-(5-iodothien-2-yl)-3',5'-di-O-acetyl-2'-deoxyuridine
  参考文献：
  名称：

  5-thien-2-yl-2'-deoxyuridine类似物的合成和抗病毒活性。

  摘要：

  使用四有机锡试剂和钯配合物作为催化剂，由5-碘-2'-脱氧尿苷合成了许多5-杂芳族取代的2'-脱氧尿苷。优化了5-碘-2'-脱氧尿苷与锡烷基化杂芳族化合物之间的钯催化的交叉偶联反应，以合成5-噻吩-3-基-2'-脱氧尿苷和5-呋喃-3-基-2' -脱氧尿苷。5-（5-碘噻吩-2-基）-2'-脱氧尿苷用作合成5-（5-甲基噻吩-2-基）-2'-脱氧尿苷，5-（5-乙烯基噻吩-2）的起始原料-基）-2'-脱氧尿苷和5-（5-乙炔基噻吩-2-基）-2'-脱氧尿苷。以硝酸铈铵为试剂合成了5-（5-硝基噻吩-2-基）-2'-脱氧尿苷。由5-（3-氧代丙炔-1-基）-2′-脱氧尿苷合成5-（异恶唑-5-基）-2′-脱氧尿苷。最后，通过将5-噻吩-2-基-β-卤化得到5-（5-氯噻吩-2-基）-β-D-阿拉伯呋喃糖基尿嘧啶和5-（5-溴噻吩-2-基）-β-D-阿拉伯呋喃糖基尿嘧啶。 D-阿拉伯呋喃糖基尿

  DOI：

  10.1021/jm00057a003
• 作为产物：
  描述：

  5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 β-5-(2-thienyl)-2'-deoxy-3',5'-di-O-acetyluridine
  参考文献：
  名称：

  5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication

  摘要：

  2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.

  DOI：

  10.1021/jm00112a011

文献信息

• NMR studies on 4-thio-5-furan-modified and 4-thio-5-thiophene-modified nucleosides
  作者：Xiao-Hui Zhang、Yao-Zhong Xu

  DOI：10.1002/mrc.4501

  日期：2016.11

  Systematic NMR characterization of 4‐thio‐5‐furan‐pyrimidine nucleosides or 4‐thio‐5‐thiophene‐pyrimidine nucleosides (ribonucleosides and 2′‐deoxynucleosides) was performed. All proton and carbon signals of 4‐thio‐5‐thiophene‐ribouridine and related analogues were unambiguously assigned. The orientations of the base (4‐thiouridine or its deoxy analogue) relative to the ring (furan or thiophene) are

  对4-硫代-5-呋喃-嘧啶核苷或4-硫代-5-噻吩-嘧啶核苷（核糖核苷和2'-脱氧核苷）进行了系统NMR表征。4-thio-5-thiophene-ribouridine 和相关类似物的所有质子和碳信号都被明确分配。通过核磁共振方法探索了碱基（4-硫尿苷或其脱氧类似物）相对于环（呋喃或噻吩）的取向，并得到了 X 射线晶体学研究的进一步支持。此处介绍的程序适用于其他修饰的核苷和核苷酸。版权所有 © 2016 John Wiley & Sons, Ltd.
• Synthesis of various 5-substituted 2′-deoxy-3′-5′-di-<i>O</i>-acetyluridines
  作者：Dan Peters、Anna-Britta Hörnfeldt、Salo Gronowitz、Nils Gunnar Johansson

  DOI：10.1002/jhet.5570280262

  日期：1991.2

  The Pd(0)-catalyzed coupling reaction of β-5-iodo-2′-deoxy-3′,5′-di-O-acetyluridine with various heteroaryltrimethylstannyl compounds gave the corresponding β-5-heteroaryl-2′-deoxy-3′,5′-di-O-acetyluridines in moderate yields. This direct coupling approach for nucleosides represented an interesting alternative to the 5-heteroaryl functionalization of pyrimidines followed by the Hilbert-Johnson glycosylation

  Pd（0）催化的β-5-碘-2'-脱氧-3'，5'-二-O-乙酰尿苷与各种杂芳基三甲基锡烷基化合物的偶联反应得到相应的β-5-杂芳基-2'-脱氧- 3'，5'-二-O-乙酰尿苷，产率中等。这种直接连接核苷的方法代表了一个有趣的替代方法，可替代嘧啶的5-杂芳基官能化，然后进行希尔伯特-约翰逊糖基化反应，该反应通常会产生α和β端基异构体的混合物。
• Design, Synthesis, and Spectroscopic Properties of Extended and Fused Pyrrolo-dC and Pyrrolo-C Analogs
  作者：Mary S. Noé、Andro C. Ríos、Yitzhak Tor

  DOI：10.1021/ol3012327

  日期：2012.6.15

  The syntheses of four fluorescent nucleoside analogs, related to pyrrolo-C (PyC) and pyrrolo-dC (PydC) through the conjugation or fusion of a thiophene moiety, are described. A thorough photophysical analysis of the nucleosides, in comparison to PyC, is reported.
• Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives
  作者：Corinne Peyron、Rachid Benhida、Christian Bories、Philippe M. Loiseau

  DOI：10.1016/j.bioorg.2005.07.001

  日期：2005.12

  We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 = 3 mu M. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used as nucleoside reference compound. Considering the cytotoxicity of synthetic compounds on peritoneal murine macrophages., the most toxic compound was MeThio-dU (3d) with a MTC at 10 mu M. Only Methia-dU (3b) was active against intramacrophagic amastigotes with an IC50 = 6.5 mu M. This latter can now be evaluated in vivo, for further investigations through structure-based drug design. (c) 2005 Elsevier Inc. All rights reserved.
• PETERS, DAN;HORNFELDT, ANNA-BRITTA;GRONOWITZ, SALO;JOHANSSON, NILS GUNNAR, J. HETEROCYCL. CHEM., 28,(1991) N, C. 529-531
  作者：PETERS, DAN、HORNFELDT, ANNA-BRITTA、GRONOWITZ, SALO、JOHANSSON, NILS GUNNAR

  DOI：——

  日期：——