5-丙炔-2-脱氧尿苷 | 84558-94-1

• 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-丙炔-2-脱氧尿苷
• 英文名称: 5-(1-propynyl)-2'-deoxyuridine
• 英文别名: 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(prop-1-yn-1-yl)pyrimidine-2,4(1H,3H)-dione；1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(prop-1-ynyl)pyrimidine-2,4(1H,3H)-dione；1-(β-D-2-deoxyribofuranosyl)-5-(prop-1-ynyl)uracil；5-propynyl-2'-deoxyuridine；2'-deoxy-5-propynyluridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-1-ynylpyrimidine-2,4-dione
• CAS: 84558-94-1
• 化学式: C₁₂H₁₄N₂O₅
• 分子量: 266.254
• InChiKey: HFJMJLXCBVKXNY-IVZWLZJFSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  5-丙炔-2-脱氧尿苷 在 吡啶 、 四氮唑 、 copper(l) iodide 、 氨 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.5h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-methyl-2-oxo-2,7-dihydro-pyrrolo[2,3-d]pyrimidin-3-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Pyrrolo-dC and pyrrolo-C: fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides

  摘要：

  Pyrrolo-dC (1a, 6-methyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) and its cyanoethyl phosphoramidite 2a were synthesized. The latter was incorporated into oligodeoxyribonucleotides by standard automated synthesis techniques, where pyrrolo-dC was found to serve as a fluorescent analog of deoxycytidine. The cyanoethylphosphoramidite (2b) of pyrrolo-C (2a, 6-methyl-3-(P-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) was also synthesized and may find use for the site-specific incorporation of a fluorescent cytidine analog into oligoribonucleotides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.108
• 作为产物：
  描述：

  5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5-丙炔-2-脱氧尿苷
  参考文献：
  名称：

  核酸相关化合物。40. 5-炔基尿嘧啶核苷的合成和生物学活性。

  摘要：

  末端炔与5-碘-1-（2,3,5-三-Op-甲苯基-β-D-阿拉伯呋喃糖基）尿嘧啶和5-碘-3'，5'-二-Op-甲苯基-2'的偶联-脱氧尿苷在三乙胺中易于催化量的双（三苯基膦）-钯（II）氯化物和碘化铜（I）进行。使所得产物脱保护，得到5-炔基-1-β-D-阿拉伯呋喃糖基尿嘧啶和5-炔基-2'-脱氧尿苷核苷。5-乙炔基，其次是5-丙炔基，产品具有最高的抗病毒效力，其中2'-脱氧衍生物比阿拉伯糖基化合物更有效。活性在己炔基处弱，而在庚炔基处消失。包含ω-羟基功能减弱了抗病毒作用。测试的5-炔基尿嘧啶核苷均没有足够的选择性足以胜任候选抗病毒药。

  DOI：

  10.1021/jm00359a008

文献信息

• Novel heterocyclic compounds, method for preparing same and use thereof as medicines, in particular as antibacterial agents
  申请人：Aszodi Joseph

  公开号：US20050245505A1

  公开（公告）日：2005-11-03

  The invention relates to new heterocyclic compounds of general formula (I), and their salts with a base or an acid: The invention also relates to a process for the preparation of these compounds, as well as their use as medicaments, in particular as anti-bacterial agents.

  这项发明涉及一般式(I)的新杂环化合物及其与碱或酸形成的盐： 该发明还涉及制备这些化合物的方法，以及它们作为药物的用途，特别是作为抗菌剂。
• [EN] siRNAs WITH AT LEAST TWO LIGANDS AT DIFFERENT ENDS<br/>[FR] ARNSI POSSÉDANT AU MOINS DEUX LIGANDS À DEUX EXTRÉMITÉS DISTINCTES
  申请人：SILENCE THERAPEUTICS GMBH

  公开号：WO2019193189A1

  公开（公告）日：2019-10-10

  There is provided inter alia a conjugate for inhibiting expression of a target gene in a cell, said conjugate comprising a nucleic acid portion and ligand portions, said nucleic acid portion comprising at least one duplex region that comprises at least a portion of a first RNA strand and at least a portion of a second RNA strand that is at least partially complementary to the first strand, wherein said first strand is at least partially complementary to at least a portion of RNA transcribed from said target gene, said ligand portions comprising a linker moiety and a targeting ligand for in vivo targeting of cells and being conjugated exclusively to the 3' and/or 5' ends of one or both RNA strands, wherein the 5' end of the first RNA strand is not conjugated, wherein: (i) the second RNA strand is conjugated at the 5' end to the targeting ligand, and wherein (a) the second RNA strand is also conjugated at the 3' end to the targeting ligand and the 3' end of the first RNA strand is not conjugated; or (b) the first RNA strand is conjugated at the 3' end to the targeting ligand and the 3' end of the second RNA strand is not conjugated; or (c) both the second RNA strand and the first RNA strand are also conjugated at the 3' ends to the targeting ligand; or (ii) both the second RNA strand and the first RNA strand are conjugated at the 3' ends to the targeting ligand and the 5' end of the second RNA strand is not conjugated.

  提供了一种用于抑制细胞中靶基因表达的共轭物，该共轭物包括核酸部分和配体部分，所述核酸部分包括至少一个双链区域，该区域包括至少部分第一RNA链和至少部分第二RNA链，该第二RNA链至少部分与第一链互补，其中所述第一链至少部分与从所述靶基因转录的RNA的至少部分互补，所述配体部分包括连接子基团和用于体内细胞靶向的靶向配体，并且仅连接到一个或两个RNA链的3'和/或5'末端，其中第一RNA链的5'末端未连接，其中：(i) 第二RNA链在5'末端连接到靶向配体，其中(a) 第二RNA链还在3'末端连接到靶向配体，且第一RNA链的3'末端未连接；或(b) 第一RNA链在3'末端连接到靶向配体，且第二RNA链的3'末端未连接；或(c) 第二RNA链和第一RNA链的3'末端均连接到靶向配体；或(ii) 第二RNA链和第一RNA链的3'末端均连接到靶向配体，且第二RNA链的5'末端未连接。
• Rapid methylation of terminal acetylenes by the Stille coupling of methyl iodide with alkynyltributylstannanes: a general protocol potentially useful for the synthesis of short-lived 11CH3-labeled PET tracers with a 1-propynyl groupElectronic supplementary information (ESI) available: general experimental remarks and synthetic methods and characterization of tributylalkynylstannanes and the corresponding methylacetylenes. See http://www.rsc.org/suppdata/ob/b3/b311532a/
  作者：Takamitsu Hosoya、Masahiro Wakao、Yurie Kondo、Hisashi Doi、Masaaki Suzuki

  DOI：10.1039/b311532a

  日期：——

  The Pd(0)-mediated rapid coupling (trapping) reaction of methyl iodide with an excess amount of alkynyltributylstannane has been developed with the aim to incorporate a short-lived (11)C-labeled methyl group into biologically active organic compounds with a 1-propynyl structural unit.

  已开发出Pd（0）介导的甲基碘与过量的炔基三丁基锡烷的快速偶联（捕获）反应，旨在将短寿命的（11）C标记的甲基掺入具有1的生物活性有机化合物中-丙炔基结构单元。
• Antiviral compounds
  申请人：Burroughs Wellcome Co.

  公开号：US05079235A1

  公开（公告）日：1992-01-07

  The present invention relates to certain novel 5-substituted pyrimidine nucleosides and pharmaceutically acceptable derivatives thereof and their use in the treatment of varicella zoster virus, cytomegalovirus and Epstein Barr virus infections. Also provided are pharmaceutical formulations and processes for the preparation of the compounds according to the invention.

  本发明涉及某些新型的5-取代嘧啶核苷及其药用可接受的衍生物，以及它们在治疗水痘-带状疱疹病毒、巨细胞病毒和EB病毒感染中的用途。同时提供了根据本发明制备该类化合物的药物配方和工艺。
• STABILIZED NUCLEIC ACID DARK QUENCHER-FLUOROPHORE PROBES
  申请人：Cook Ronald M.

  公开号：US20090259030A1

  公开（公告）日：2009-10-15

  The present invention provides a new class of solids supports for synthesis of modified oligomers of nucleic acids, and nucleic acid probes that have a format expediently synthesized on the new supports. Exemplary solid supports include at least one quencher bound through a linker to the solid support. Various exemplary embodiments include a moiety that stabilizes a duplex, triplex or higher order aggregation (e.g., hybridization) of nucleic acids of which the oligomer of the invention is a component. Other components of the solid support include moieties that stabilize aggregations of nucleic acids, e.g., intercalators, minor groove binding moieties, bases modified with a stabilizing moiety (e.g., alkynyl moieties, and fluoroalkyl moieties), and conformational stabilizing moieties, such as those described in commonly owned U.S. Patent Application Publication No. 2007/0059752.

  本发明提供了一种新型固体支持体，用于合成修饰寡核苷酸的新类固体支持体以及具有在新支持体上方便合成的核酸探针。示例固体支持体包括至少通过连接剂与固体支持体结合的一个猝灭剂。各种示例实施例包括稳定双链、三链或更高级别聚集（例如，杂交）的基团，其中该发明的寡聚物是其中的一个组分的基团。固体支持体的其他组分包括稳定核酸聚集的基团，例如，插入剂、小沟结合基团、经过稳定基团修饰的碱基（例如，炔基基团和氟烷基团）和构象稳定基团，例如，如同在共同拥有的美国专利申请公开号2007/0059752中描述的那样。