2'-allyl-2'-deoxyuridine | 151384-09-7

• 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: 2'-allyl-2'-deoxyuridine
• 英文别名: 2'-C-allyl-2'-deoxyuridine；2'-C-α-allyl-2'-deoxyuridine；(2'R)-2'-DEOXY-2'C-ALLYLURIDINE；(2'r)-2'-Deoxy-2'-c-allyluridine；1-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-prop-2-enyloxolan-2-yl]pyrimidine-2,4-dione
• CAS: 151384-09-7
• 化学式: C₁₂H₁₆N₂O₅
• 分子量: 268.269
• InChiKey: PWQSWGAOGJANRE-DEKFOEGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2'-allyl-2'-deoxyuridine 在 吡啶 、 咪唑 、 N-羟基丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 thiocarbonic acid O-[4-allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-phenyl ester
  参考文献：
  名称：

  Synthesis of 2′,3′-Cyclohexen Bicyclic Uridine Analogues Using Ring-Closure Metathesis

  摘要：

  本文介绍了两种新的 2′,3′-环己烯双环尿苷类似物的合成。由 5′保护尿苷在 2′-C和 3′-C位置连续进行两次锡自由基介导的烯丙基化反应，然后使用格拉布斯催化剂在二烯中间体上进行闭环烯烃偏聚反应，最终形成六元环。

  DOI：

  10.1055/s-2006-941568
• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)尿苷 在 吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 2'-allyl-2'-deoxyuridine
  参考文献：
  名称：

  使用闭环烯烃和烯炔复分解反应合成构象受限的核酸片段

  摘要：

  为了构建用于识别二级 RNA 结构的构象限制性核酸片段，我们合成了不同的含有额外环的单核苷酸和二核苷酸。这些环是通过从已引入双键或三键的核苷酸底物通过闭环烯烃或烯炔复分解反应制备的。

  DOI：

  10.1081/ncn-200060347

文献信息

• [EN] TARGETED DELIVERY TO BETA CELLS<br/>[FR] ADMINISTRATION CIBLÉE À DES CELLULES BÊTA
  申请人：CHOUDHARY AMIT

  公开号：WO2018195486A1

  公开（公告）日：2018-10-25

  The disclosure includes zinc prodrugs for targeted delivery of therapeutic, diagnostic or imaging agents to β-cells and methods of use therefor. The disclosure also includes targeted delivery of small molecules to β-cells that stabilize and activate CRISPR effector proteins comprising at least one destabilization domain, to enable CRISPR-based genome editing and transcriptional activation or repression in β-cells.

  本公开内容包括用于将治疗性、诊断性或成像剂靶向递送至β细胞的锌前药及其使用方法。本公开内容还涉及将小分子靶向递送至β细胞，这些小分子能够稳定并激活至少含有一个不稳定域的CRISPR效应蛋白，从而在β细胞中实现基于CRISPR的基因编辑和转录激活或抑制。
• Stabilisation of a nucleic acid three-way junction by an oligonucleotide containing a single 2′-C to 3′-O-phosphate butylene linkage prepared by a tandem RCM-hydrogenation method
  作者：Philip Børsting、Katrine E. Nielsen、Poul Nielsen

  DOI：10.1039/b502720a

  日期：——

  A cyclic dinucleotide with a butylene linker between the upper 2′-C position and the 3′-O-phosphate linkage was synthesised from simple nucleoside building blocks via a tandem ring-closing metathesis and hydrogenation procedure. The major of two phosphorus epimers was incorporated into an oligodeoxynucleotide, as well as into an LNA–DNA mixmer oligonucleotide. These were evaluated as parts in three different secondary structures, a duplex, a bulged duplex and a three-way junction, with both DNA and RNA complements. In the DNA : RNA hybrid molecule, the oligodeoxynucleotide containing this single 2′-C to 3′-O-phosphate butylene linkage was found to stabilise a three-way junction.

  通过串联闭环偏析和氢化过程，从简单的核苷结构单元合成了一种环状二核苷酸，其上部 2â²-C 位置和 3â²-O- 磷酸连接之间带有丁烯连接体。两个磷表聚物的主要部分被整合到一个寡聚脱氧核苷酸和一个 LNAâDNA 混合寡聚核苷酸中。评估结果显示，这些寡核苷酸具有三种不同的二级结构，即双链、凸起双链和三向结，同时具有 DNA 和 RNA 互补。在 DNA 与 RNA 的杂交分子中，发现含有这种单一 2²-C 至 3²-O 磷酸丁烯连接的寡脱氧核苷酸能稳定三向连接。
• Nucleoside triphosphates and their incorporation into ribozymes
  申请人：RIBOZYME PHARMACEUTICALS, INC.

  公开号：EP1493818A2

  公开（公告）日：2005-01-05

  Novel nucleotide triphosphates, methods of synthesis and process of incorporating these nucleotide triphosphates into oligonucleotides, and isolation of novel nucleic acid catalysts (e.g. ribozymes) are disclosed.

  公开了新型核苷酸三磷酸酯、将这些核苷酸三磷酸酯加入寡核苷酸的合成方法和工艺，以及新型核酸催化剂（如核糖酶）的分离。
• A method for local administration of synthetic double-stranded oligonucleotides targeting a VEGF receptor
  申请人：SIRNA THERAPEUTICS, INC.

  公开号：EP1767632A2

  公开（公告）日：2007-03-28

  The present invention relates to nucleic acid molecules, including dsRNA, siRNA, antisense, 2,5-A chimeras, aptamers, and enzymatic nucleic acid molecules, such as hammerhead ribozymes, DNAzymes, and allozymes, which modulate the expression of vascular endothelial growth factor receptor (VEGF) and/or vascular endothelial growth factor receptor (VEGFr) genes for the treatment and/or diagnosis of diseases and conditions associated with angiogenesis, such as cancer, tumor angiogenesis, or ocular indications such as diabetic retinopathy, or age related macular degeneration, proliferative diabetic retinopathy, hypoxia-induced angiogenesis, rheumatoid arthritis, psoriasis, wound healing, and female reproductive disorders and conditions, including but not limited to endometriosis, endometrial carcinoma, gynecologic bleeding disorders, irregular menstrual cycles, ovulation, premenstrual syndrome (PMS), and menopausal dysfunction.

  本发明涉及调节血管内皮生长因子受体（VEGF）和/或血管内皮生长因子受体（VEGFr）基因表达的核酸分子，包括dsRNA、siRNA、反义、2,5-A嵌合体、aptamers和酶核酸分子，如锤头核酶、DNA酶和同工酶，用于治疗和/或诊断与血管生成有关的疾病和病症，如癌症、肿瘤血管生成，或眼部适应症，如糖尿病视网膜病变或老年性黄斑变性、增殖性糖尿病视网膜病变、缺氧诱导的血管生成、类风湿性关节炎、牛皮癣、伤口愈合、以及女性生殖系统疾病和病症，包括但不限于子宫内膜异位症、子宫内膜癌、妇科出血性疾病、月经周期不规律、排卵、经前综合征 (PMS) 和更年期功能障碍。
• Methods of treating vestibular schwannoma and reducing hearing or neurite loss caused by vestibular schwannoma
  申请人：Massachusetts Eye and Ear Infirmary

  公开号：US10010585B2

  公开（公告）日：2018-07-03

  Methods to reduce the proliferation of vestibular schwannoma (VS) cells and/or provide neuroprotection to reduce the risk of sensorineural hearing loss (SNHL), vestibular dysfunction and facial nerve paralysis in subjects with VS. The methods can include one or more of decreasing TNF-α activity or expression; decreasing NF-κB expression or activity; decreasing COX-2 expression or activity; administering FGF2; decreasing HGF expression or activity; or decreasing c-Met expression or activity.

  减少前庭分裂瘤（VS）细胞增殖和/或提供神经保护以降低 VS 患者感音神经性听力损失（SNHL）、前庭功能障碍和面神经麻痹风险的方法。这些方法可包括降低 TNF-α 活性或表达；降低 NF-κB 表达或活性；降低 COX-2 表达或活性；施用 FGF2；降低 HGF 表达或活性；或降低 c-Met 表达或活性中的一种或多种。