1-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide | 139621-03-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 1-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide
• 英文别名: 2',3'-di-O-benzoylribavirin；1-(2,3-Di-O-benzoyl-β-D-ribofuranosyl)-1H-1,2,4,-triazole-3-carboxamide；1-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide；[(2R,3R,4R,5R)-4-benzoyloxy-5-(3-carbamoyl-1,2,4-triazol-1-yl)-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 139621-03-7
• 化学式: C₂₂H₂₀N₄O₇
• 分子量: 452.423
• InChiKey: YDFVLIROMVIVAI-WOCWXWTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 在 吡啶 、 三甲基乙酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.41h， 生成
  参考文献：
  名称：

  Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases

  摘要：

  IMPDH inhibitors have potential antimicrobial, anticancer and immunomodulatory effects. Nucleoside inhibitors of IMPDH exert their inhibitory effects via nucleoside 5'-MPs. Conversion of nucleoside analogs to NMPs by cellular nucleoside kinases is not assured, and usually is inefficient. In order to bypass cellular phosphorylation, a series of azole nucleoside 5'-MP mimics (P1Ms) based on ribavirin, EICAR and bredinin were synthesized and screened against human and C. albicans IMP dehydrogenises. P1Ms 8, 16, 25, 28 and 29 demonstrated substantial IMPDH inhibition with K-i values in low micromolar range.

  DOI：

  10.1081/ncn-120027838
• 作为产物：
  描述：

  利巴韦林 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 66.25h， 生成 1-(2,3-di-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  核苷酸。第LII部分。新型碱基修饰的（2'-5'）寡腺苷酸三聚体的合成和生物活性†

  摘要：

  一些新的（2'-5'）寡腺苷酸三聚物，即，22 - 28，含有该抗病毒核苷利巴韦林（= 1-（β-d-D-呋喃核糖基）-1 ħ -1,2,4-三唑-3-甲酰胺; 7）和合成的细胞因子的6-（苄基氨基）嘌呤核苷（= N 6 -benzyladenosine; 1在三聚体的不同位置），已经通过磷酸三酯法合成。所述选择性阻断核苷2 - 6和8 - 11和2'-磷酸二酯13和14，用于寡核苷酸合成中，由相应的未保护的核糖核苷合成1和7，并通过硅胶柱色谱法分离。完全脱保护的三聚体22 - 28通过在离子交换色谱法纯化，DEAE - Senacell 23 - SS。通过物理手段对新合成的化合物进行了表征。研究了合成的三聚体抑制HIV-1复制和改善RNase L活化的能力。一些合成的三聚体还显示出对HIV-1逆转录酶和HIV-1诱导的合胞体形成的生物抑制作用。结果表明，含Ado Bn的三聚体可抑制HIV-1诱导的合胞体形成>

  DOI：

  10.1002/hlca.19970800404

文献信息

• Base-modified derivatives of 2′,5′-oligoadenylate and antiviral uses thereof
  申请人：Temple University- of the Commonwealth System of Higher Education

  公开号：US06281201B1

  公开（公告）日：2001-08-28

  Antiviral compounds have the formula wherein m is zero, 1, 2 or 3; n is from 1 to 8, preferably 1, 2 or 3; most preferably 1 or 2; R is independently selected from the group consisting of  provided that all R may not be R1 is independently selected from the group consisting of hydroxyl and hydrogen; R2 is independently selected from the group consisting of oxygen and sulfur; or water soluble salts thereof.

  抗病毒化合物的化学式为其中m为零、1、2或3；n为1至8，优选1、2或3；最优选1或2；R从以下组成的群体中独立选择，假设所有的R不全为R1：R1从羟基和氢中独立选择；R2从氧和硫中独立选择；或其水溶性盐。
• Nucleoside 5'-monophosphate mimics and their prodrugs
  申请人：——

  公开号：US20040023901A1

  公开（公告）日：2004-02-05

  The present invention relates to novel nucleoside 5′-monophosphate mimics, which contain novel nucleoside bases and phosphate moiety mimics optionally having sugar-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, anticancer, and immunomodulatory 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.

  本发明涉及一种新型的核苷酸5'-单磷酸类似物，其中包含新型的核苷酸碱基和磷酸基类似物，可选择具有糖基修饰。本发明的核苷酸类似物以药学可接受的盐、药学可接受的前药或制剂的形式，作为抗病毒、抗微生物、抗癌和免疫调节剂。本发明提供了一种治疗病毒感染、微生物感染和增殖性疾病的方法。本发明还涉及包含本发明化合物的药物组合物，可选择与其他药学活性剂组合使用。
• ANTI-CANCER PHOSPHONATE ANALOGS
  申请人：Boojamra Constantine G.

  公开号：US20100022467A1

  公开（公告）日：2010-01-28

  The invention is related to phosphorus substituted anti-cancer compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  本发明涉及磷取代的抗癌化合物、含有这些化合物的组合物以及包括给予这些化合物的治疗方法，还涉及用于制备这些化合物的过程和中间体。
• ANTIVIRAL PHOSPHONATE ANALOGS
  申请人：Boojamra Constantine G.

  公开号：US20090275535A1

  公开（公告）日：2009-11-05

  The invention is related to phosphorus substituted compounds with antiviral activity, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  这项发明涉及具有抗病毒活性的磷取代化合物，包含这种化合物的组合物以及包括给予这种化合物的治疗方法，还包括用于制备这种化合物的过程和中间体。
• Synthesis and Biological Activity of New 2′ 5′-Oligonucleotides
  作者：Evgeny I. Kvasyuk、Tamara I. Kulak、Igor A. Mikhailopulo、Robert J. Suhadolnik、Earl E. Henderson、Susan E. Horvath、Ming-Xu Guan、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006186

  日期：1997.7

  Some new 2',5'-oligonucleotide trimers containing the antiviral nucleoside ribavirin and the cytokine 6-benzylaminopurine riboside in different position of the oligos have been synthesized. Some of the trimers showed biological inhibitions of HIV-1 reverse transcriptase, HIV-1 induced syncytia formation and activation of RNase L.