5-(2-carbethoxyethyl)-2'-deoxyuridine | 128870-20-2

• 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: 5-(2-carbethoxyethyl)-2'-deoxyuridine
• 英文别名: 5-(2-Carboxyethyl)-2'-deoxyuridine；3-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]propanoic acid
• CAS: 128870-20-2
• 化学式: C₁₂H₁₆N₂O₇
• 分子量: 300.268
• InChiKey: JVPCNZGWRVIZFZ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(2-carbethoxyethyl)-2'-deoxyuridine 在 吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 5'-O--5-<3-<<2-<<<1--1H-imidazol-4-yl>acetyl>amino>ethyl>amino>-3-oxopropyl>-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and characterization of nucleoside peptides: toward chemical ribonucleases. 1

  摘要：

  DOI：

  10.1021/jo00304a026
• 作为产物：
  描述：

  碘苷 在 palladium on activated charcoal palladium diacetate 、 sodium hydroxide 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 丙酮 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 36.0h， 生成 5-(2-carbethoxyethyl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of 5-Tethered Carborane-Containing Pyrimidine Nucleosides as Potential Agents for DNA Incorporation

  摘要：

  Several 5-substituted-2'-deoxyuridines have been prepared in which the carborane moiety is attached at the terminus of a flexible hydrocarbon chain containing an ester linkage. These boron moieties as the B-10 enriched compounds have potentiality for use in the treatment of cancer by means of boron neutron capture therapy. A convenient synthetic route, in high yield, has been developed for the preparation of these 5-tethered carborane-containing pyrimidine nucleosides.

  DOI：

  10.1080/15257779408010680

文献信息

• Water-proton relaxivities of DNA oligomers carrying TEMPO radicals
  作者：Yuichiro Sato、Hiroyuki Hayashi、Manami Okazaki、Mariko Aso、Satoru Karasawa、Shoji Ueki、Hiroshi Suemune、Noboru Koga

  DOI：10.1002/mrc.2310

  日期：2008.11

  5‐Uridine derivative carrying a TEMPO radical (UST) was prepared and its single strand (ssUST) and a double strand (dsUST) with its complementary strand were obtained. Similarly, single strands carrying two and five radicals (ssUST2 and ssUST5, respectively) and the corresponding double strands (dsUST2 and dsUST5) were prepared. Their electron paramagnetic resonance (EPR) spectra showed typical anisotropic

  制备了带有 TEMPO 自由基 (UST) 的 5-尿苷衍生物，并获得了其单链 (ssUST) 和带有互补链的双链 (dsUST)。类似地，制备带有两个和五个基团（分别为 ssUST2 和 ssUST5）的单链和相应的双链（dsUST2 和 dsUST5）。他们的电子顺磁共振 (EPR) 光谱在高场线中显示出典型的各向异性展宽。对于 UST、ssUSTm 和 dsUSTm，通过分析 EPR 谱估计的旋转相关时间 τR 分别为 1.1 × 10−10、5.9 × 10−10 和 14 × 10−10 s。25 MHz、0.59 T 和 25 °C 下的水质子弛豫率 r1 和 r2 也以相同的顺序增加，UST、ssUSTm 的 r1 值为 0.26、0.41 和 0.56 mM-1 s-1。和 dsUSTm，分别。r1 值为 1.00 和 2。分别获得了 dsUST2 和 dsUST5 的 06
• Compounds and methods for trans-membrane delivery of molecules
  申请人：Aposense LTD.

  公开号：US10195286B2

  公开（公告）日：2019-02-05

  A conjugate for delivery of drugs, such as genetic drugs, [e.g., siRNA, dsiRNA, or antisense oligonucleotides (ASO)] across biological membranes is provided. The conjugates of the Invention are capable of delivering drugs in both presence and absence of plasma proteins.

  本发明提供了一种用于跨生物膜递送药物（如基因药物）[如 siRNA、dsiRNA 或反义寡核苷酸 (ASO)]的共轭物。本发明的共轭物能够在存在或不存在血浆蛋白的情况下递送药物。
• Building Blocks for Ribozyme Mimics:  Conjugates of Terpyridine and Bipyridine with Nucleosides
  作者：James K. Bashkin、Jin Xie、Andrew T. Daniher、UmaShanker Sampath、Jeffrey L.-F. Kao

  DOI：10.1021/jo9518213

  日期：1996.1.1

  The incorporation of the 2,2':6',2 ''-terpyridyl (terpy) complex of Cu(II) into a deoxyoligonucleotide has led to a functional mimic of ribozymes. The resulting mimic can cleave target RNA in a sequence-directed manner by a hydrolytic mechanism. Here we describe the synthesis and characterization of four modified nucleoside phosphoramidite reagents (7, 10, 14, and 18) that contain pendant 2,2'-bipyridine or terpy ligands. The ligands are attached either to the nucleobase (7, 10) or to the sugar (14, 18). Nucleobase modification was carried out at the C-5 position of 2'-deoxyuridine (dU). One route to sugar modification was performed by synthesis of 18, a 1'-functionalized analog of dU based on 1-[3-deoxy-beta-D-psicofuranosyl]uracil. Another route to sugar functionaliztion resulted in 14, a 2'-O-alkyl derivative of adenosine. These modified nucleosides are building blocks for ribozyme mimics. They are designed to deliver hydrolytically active metal complexes across either the major groove (7, 10) or the minor groove (14, 18) of an RNA/DNA duplex.
• Bashkin; Frolova; Sampath, Journal of the American Chemical Society, 1994, vol. 116, # 13, p. 5981 - 5982
  作者：Bashkin、Frolova、Sampath

  DOI：——

  日期：——
• BASHKIN, JAMES K.;GARD, JANICE K.;MODAK, ANIL S., J. ORG. CHEM., 55,(1990) N7, C. 5125-5132
  作者：BASHKIN, JAMES K.、GARD, JANICE K.、MODAK, ANIL S.

  DOI：——

  日期：——