1-(5-deoxy-5-iodo-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide | 594860-49-8

• 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-(5-deoxy-5-iodo-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide
• 英文别名: 1-(5-iodo-5-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide；1-(5-Deoxy-5-iodo-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide；1-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(iodomethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
• CAS: 594860-49-8
• 化学式: C₈H₁₁IN₄O₄
• 分子量: 354.104
• InChiKey: ZVRTTWVEECDAIA-AFCXAGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-deoxy-5-iodo-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1-(5-deoxy-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  三唑核苷衍生物的合成

  摘要：

  摘要 5'-O-Mesyl-2',3'-O-异亚丙基核糖核苷（4 和 12）通过与 NaN3 或 KI 反应以良好的产率转化为其 5'-取代的核苷。2',3'-O-异亚丙基核糖核苷（3 和 11）是从核糖核苷 1 和 2 用丙酮和原甲酸三乙酯的反应混合物而不是使用丙酮二乙缩醛以良好的产率制备的。化合物 1 或 2 用 2-乙酰氧基异丁酰卤（Cl 或 Br）处理，得到 1-[2-O-acetyl-3-halo-3-deoxy-5-O-(2,5,5-trimethyl-1, 3-dioxolan-4-on-2-yl)-β-D-xylofuranosyl]-1,2,4-triazole-3-carboxamide (19, 22, and 23) 高产率。22 和 23 的合成中不使用 2-乙酰氧基异丁酰溴，而是使用 2-乙酰氧基异丁酰氯和 NaBr 的混合物。用活化的 Zn/Cu 对处理 19

  DOI：

  10.1081/ncn-120022032
• 作为产物：
  描述：

  1-(5-iodo-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以83%的产率得到1-(5-deoxy-5-iodo-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  三唑核苷衍生物的合成

  摘要：

  摘要 5'-O-Mesyl-2',3'-O-异亚丙基核糖核苷（4 和 12）通过与 NaN3 或 KI 反应以良好的产率转化为其 5'-取代的核苷。2',3'-O-异亚丙基核糖核苷（3 和 11）是从核糖核苷 1 和 2 用丙酮和原甲酸三乙酯的反应混合物而不是使用丙酮二乙缩醛以良好的产率制备的。化合物 1 或 2 用 2-乙酰氧基异丁酰卤（Cl 或 Br）处理，得到 1-[2-O-acetyl-3-halo-3-deoxy-5-O-(2,5,5-trimethyl-1, 3-dioxolan-4-on-2-yl)-β-D-xylofuranosyl]-1,2,4-triazole-3-carboxamide (19, 22, and 23) 高产率。22 和 23 的合成中不使用 2-乙酰氧基异丁酰溴，而是使用 2-乙酰氧基异丁酰氯和 NaBr 的混合物。用活化的 Zn/Cu 对处理 19

  DOI：

  10.1081/ncn-120022032

文献信息

• Azido nucleosides and nucleotide analogs
  申请人：Alios BioPharma, Inc.

  公开号：US09346848B2

  公开（公告）日：2016-05-24

  Disclosed herein are 4′-azido-substituted nucleosides, nucleotides and analogs thereof, pharmaceutical compositions that include one or more of 4′-azido-substituted nucleosides, nucleotides and analogs thereof, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an infection from a paramyxovirus and/or an orthomyxovirus, with a 4′-azido-substituted nucleoside, a nucleotide and/or an analog thereof. Examples of viral infections include a respiratory syncytial viral (RSV) and influenza infection.

  本文披露了4'-偶氮基取代核苷、核苷酸及其类似物，包括其中一个或多个4'-偶氮基取代核苷、核苷酸及其类似物的药物组合物，以及它们的合成方法。本文还披露了使用4'-偶氮基取代核苷、核苷酸和/或其类似物来改善和/或治疗疾病和/或病况的方法，包括由副粘病毒和/或正粘病毒引起的感染。病毒感染的例子包括呼吸道合胞病毒（RSV）和流感感染。
• AZIDO NUCLEOSIDES AND NUCLEOTIDE ANALOGS
  申请人：Beigelman Leonid

  公开号：US20120070415A1

  公开（公告）日：2012-03-22

  Disclosed herein are nucleosides, nucleotides and analogs thereof, pharmaceutical compositions that include one or more of nucleosides, nucleotides and analogs thereof, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an infection from a paramyxovirus and/or an orthomyxovirus, with a nucleoside, a nucleotide and an analog thereof. Examples of viral infections include a respiratory syncytial viral (RSV) and influenza infection.

  本文披露了核苷、核苷酸及其类似物，包括一个或多个核苷、核苷酸及其类似物的药物组合物，以及合成它们的方法。本文还披露了利用核苷、核苷酸和其类似物来改善和/或治疗疾病和/或状况的方法，包括来自副黏病毒和/或正黏病毒的感染。病毒感染的例子包括呼吸道合胞病毒（RSV）和流感感染。
• 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。
• Synthesis of Azole Nucleoside 5′‐Monophosphate Mimics (P1Ms) and Their Inhibitory Properties of IMP Dehydrogenases
  作者：Guangyi Wang、Kandasamy Sakthivel、Vasanthakumar Rajappan、Thomas W. Bruice、Kathleen Tucker、Patrick Fagan、Jennifer L. Brooks、Tiffany Hurd、Janet M. Leeds、P. Dan Cook

  DOI：10.1081/ncn-120027838

  日期：2004.1.1

  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.
• NUCLEOSIDE 5'-MONOPHOSPHATE MIMICS AND THEIR PRODRUGS
  申请人：Biota, Inc.

  公开号：EP1485396A2

  公开（公告）日：2004-12-15