5-(3-Amino-prop-1-ynyl)-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione | 289676-20-6

• 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-(3-Amino-prop-1-ynyl)-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• 英文别名: uridine, 5-(3-amino-1-propynyl)-2'-O-methyl-；5-(3-aminoprop-1-ynyl)-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 289676-20-6
• 化学式: C₁₃H₁₇N₃O₆
• 分子量: 311.294
• InChiKey: ONCUXKRQXRIRDI-DNRKLUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(3-Amino-prop-1-ynyl)-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 在 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.33h， 生成 [(2R,3R,4R,5R)-5-[5-[3-[[2-[1-(diphenylcarbamoyl)imidazol-4-yl]acetyl]amino]prop-1-ynyl]-2,4-dioxopyrimidin-1-yl]-2-[[hydroxy-[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl]oxymethyl]-4-methoxyoxolan-3-yl] acetate
  参考文献：
  名称：

  Functionalized nucleoside 5′-triphosphates for in vitro selection of new catalytic ribonucleic acids

  摘要：

  A series of novel 2'-modified nucleoside 5'-triphosphates was synthesized. The amino, imidazole, and carboxylate functionalities were attached to the 5-position of pyrimidine base of these molecules through alkynyl and alkyl spacers, respectively. Two different phosphorylation methods were used to optimize the yields of these highly modified triphosphates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00226-2
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-5-(5-iodo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-methoxy-tetrahydro-furan-3-yl ester 在 ammonium hydroxide 、 copper(l) iodide 、 (Ph₃P)4P 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 5-(3-Amino-prop-1-ynyl)-1-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Functionalized nucleoside 5′-triphosphates for in vitro selection of new catalytic ribonucleic acids

  摘要：

  A series of novel 2'-modified nucleoside 5'-triphosphates was synthesized. The amino, imidazole, and carboxylate functionalities were attached to the 5-position of pyrimidine base of these molecules through alkynyl and alkyl spacers, respectively. Two different phosphorylation methods were used to optimize the yields of these highly modified triphosphates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00226-2

文献信息

• Nucleotide triphosphates and their incorporation into oligonucleotides
  申请人：——

  公开号：US20030004122A1

  公开（公告）日：2003-01-02

  The present invention relates to 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 or DNAzymes). Also, provided are the use of novel enzymatic nucleic acid molecules to inhibit HER2/neu/ErbB2 gene expression and their applications in human therapy.

  本发明涉及新颖的核苷酸三磷酸盐，合成方法和将这些核苷酸三磷酸盐合成到寡核苷酸中的过程，以及新颖的核酸催化剂（例如核糖酶或DNA酶）的分离。此外，提供了使用新型酶促核酸分子抑制HER2 / neu / ErbB2基因表达的方法，并将其应用于人类治疗。
• NUCLEIC ACID BASED MODULATORS OF GENE EXPRESSION
  申请人：RIBOZYME PHARMACEUTICALS, INC.

  公开号：EP1212416A2

  公开（公告）日：2002-06-12
• JP2004512810A
  申请人：——

  公开号：JP2004512810A

  公开（公告）日：2004-04-30
• US6528640B1
  申请人：——

  公开号：US6528640B1

  公开（公告）日：2003-03-04
• US6617438B1
  申请人：——

  公开号：US6617438B1

  公开（公告）日：2003-09-09