2'-C-methyl-6-azauridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-C-methyl-6-azauridine
• 英文别名: 2-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-1,2,4-triazine-3,5-dione
• 化学式: C₉H₁₃N₃O₆
• 分子量: 259.219
• InChiKey: IWMHQAONXWQLOC-FJGDRVTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-C-methyl-6-azauridine 在 甲酸 、 叔丁基氯化镁 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 31.0h， 生成 isopropyl ((S)-(((2R,3R,4R,5R)-5-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-3,4-dihydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate
  参考文献：
  名称：

  [EN] MODIFIED NUCLEOSIDES AND NUCLEOTIDES ANALOGS AS ANTIVIRAL AGENTS FOR CORONA AND OTHER VIRUSES
  [FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES MODIFIÉS UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX CONTRE LE CORONAVIRUS ET D'AUTRES VIRUS

  摘要：

  Compounds, compositions and methods for preventing, treating or curing a coronavirus infection in human subjects or other animal hosts. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV-2. In another embodiment, the methods are used to treat a patient infected with a Flavivirus, Picornavus, Togavirus, or Bunyavirus.

  公开号：

  WO2022217154A2
• 作为产物：
  描述：

  1,3,5-三苯甲酰基-D-呋喃核糖 在 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 氨 、 四氯化钛 、 四氯化锡 、 magnesium sulfate 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2'-C-methyl-6-azauridine
  参考文献：
  名称：

  A concise synthesis of 2′-c-methylribonucleosides

  摘要：

  2'-C-Methylribonucleosides were synthesized in five steps from commercially available 1,3,5-tri-O-benzoyl-alpha-D-ribose with good overall yields.

  DOI：

  10.1016/0040-4039(95)01635-u

文献信息

• [EN] COMPOSITIONS AND METHODS FOR SYNTHESIS OF PHOSPHORYLATED MOLECULES<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE SYNTHÈSE DE MOLÉCULES PHOSPHORYLÉES
  申请人：UNIV CALIFORNIA

  公开号：WO2019195494A1

  公开（公告）日：2019-10-10

  The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

  这项发明提供了合成磷酸化有机化合物的组合物和方法，包括核苷三磷酸。
• Nucleotide mimics and their prodrugs
  申请人：——

  公开号：US20040059104A1

  公开（公告）日：2004-03-25

  The present invention relates to nucleoside diphosphate mimics and nucleoside triphosphate mimics, which contain diphosphate or triphosphate moiety mimics and optionally sugar-modifications and/or base-modifications. The nucleotide mimics of the present invention, in a form of a pharmaceutically acceptable salt, a pharmaceutically acceptable prodrug, or a pharmaceutical formulation, are useful as antiviral, antimicrobial, and anticancer agents. The present invention provides a method for the treatment of viral infections, microbial infections, and proliferative disorders. The present invention also relates to pharmaceutical compositions comprising the compounds of the present invention optionally in combination with other pharmaceutically active agents.

  本发明涉及核苷二磷酸模拟物和核苷三磷酸模拟物，其中包含二磷酸或三磷酸基团模拟物，以及可选的糖修饰和/或碱基修饰。本发明的核苷酸模拟物，以药学上可接受的盐、药学上可接受的前药或药物配方的形式，可用作抗病毒、抗微生物和抗癌剂。本发明提供了一种治疗病毒感染、微生物感染和增生性疾病的方法。本发明还涉及包含本发明化合物的药物组合物，可选地与其他药理活性剂结合。
• Compositions and methods for synthesis of phosphorylated molecules
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US11021497B2

  公开（公告）日：2021-06-01

  The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.

  本发明提供了合成磷酸化有机化合物（包括核苷三磷酸酯）的组合物和方法。
• [EN] NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION<br/>[FR] DERIVES NUCLEOSIDIQUES DESTINES AU TRAITEMENT DE L'INFECTION PAR LE VIRUS DE L'HEPATITE C
  申请人：——

  公开号：WO2003093290A3

  公开（公告）日：2004-03-18
• A Short, Flexible Route toward 2‘-<i>C</i>-Branched Ribonucleosides
  作者：Rogers E. Harry-O'kuru、Jennifer M. Smith、Michael S. Wolfe

  DOI：10.1021/jo961893+

  日期：1997.3.1

  A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-0-benzoyl-alpha-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC drop CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the beta-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.