1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione | 181711-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione
• 英文别名: (4aR,7R,8S,8aS) 1-(8-hydroxy-2-phenyl-hexahydropyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione；1-[(4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]pyrimidine-2,4-dione
• CAS: 181711-37-5
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: IDFUKFNBRGKODO-YJTWFRKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 吡啶 、 乙醇 、 水 为溶剂， 反应 83.0h， 生成 Acetic acid (4aR,7R,8R,8aS)-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  Synthesis and antiviral activity of 2-deoxy-1,5-anhydro-D-mannitol nucleosides containing a pyrimidine base moiety

  摘要：

  Nucleoside analogues containing a 2-deoxy-1,5-anhydro-D-mannitol and a pyrimidine base moiety were synthesized starting from D-glucose via a nucleophilic opening of an epoxide with the heterocyclic base and an inversion of configuration at the 3'-position. Study of the conformation of these molecules, that show some activity against herpesviruses (HSV, VZV, CMV) should increase our understanding of the structural requirements of hexitol nucleosides for antiviral activity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00244-2
• 作为产物：
  描述：

  尿嘧啶 、 1,5:2,3-二脱水-4,6-O-亚苄基-D-蒜糖醇 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 25.0h， 以29%的产率得到1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  [EN] METHOD OF PREPARATION OF NOVEL NUCLEOSIDE ANALOGS AND USES
  [FR] PROCEDE POUR PREPARER DE NOUVEAUX ANALOGUES DE NUCLEOSIDE, ET LEURS UTILISATIONS

  摘要：

  描述了制备式(A)的外消旋和光学活性核苷类似物的过程。这些化合物可用作抗感染剂、反义治疗剂和杂交分析探针。

  公开号：

  WO2005049582A1

文献信息

• Alkylated hexitol nucleoside analogues and oligomers thereof
  申请人：——

  公开号：US20040033967A1

  公开（公告）日：2004-02-19

  The present invention is directed to nucleoside analogues with as substitute for the sugar part a 1,5-anhydrohexitol moiety, doexygenated and substituted with a nucleobase at the 2-position, of which the hexitorl ring is further substituted with at least one alkoxy substituent at the 3-position or at the 1-position, and to oligonucleotides wherein at least some of the nucleotides are part of the afore mentioned hexitol nucleoside analogues and exhibit sequence-specific hydridization to complementary sequences of nucleic acids, and maintaining or improving the hybridisation strength. The invention further relates to nucleoside analogues with a 1,5-anhydrohexitol moiety as the sugar part, deoxygenated and substituted with a nucleobase at the 2-position, of which the hexitol ring is substituted with a methoxy substituent at the 1-position, having at the same time either a hydroxy or an alkoxy group at the 3-position, or having a 3-deoxygenated position. The inclusion of one or more of the afore mentioned hexitol nucleoside analogues in oligonucleotides provides, inter alia, either for improved binding or for maintained binding of these oligonucleotides to a complementary strand. This invention further relates to the chemical synthesis of these oligomers which are useful diagnostics, therapeutics and as research agents.

  本发明涉及以1,5-脱水己糖基取代糖部分的核苷类似物，其在2位上以核碱基进行脱氧和取代，其中己糖环在3位或1位进一步取代至少一个烷氧基取代基，以及寡核苷酸，其中至少一些核苷酸是前述己糖核苷类似物的一部分，并对核酸的互补序列表现出序列特异性杂交，并维持或提高杂交强度。本发明还涉及以1,5-脱水己糖基为糖部分、在2位上脱氧和取代核碱基、在己糖环上以甲氧基取代基在1位取代、同时在3位具有羟基或烷氧基，或者在3位脱氧的核苷类似物。在寡核苷酸中包含前述己糖核苷类似物中的一个或多个，可提供改进的结合或维持这些寡核苷酸与互补链的结合。本发明还涉及这些寡聚体的化学合成，它们是有用的诊断、治疗和研究试剂。
• Method of preparation of novel nucleoside analogs and uses
  申请人：Tse Bruno

  公开号：US20110070192A1

  公开（公告）日：2011-03-24

  Processes for the preparation of racemic and optically active nucleoside analogs of formula (A) are described. These compounds are useful as anti-infective agents, antisense therapeutic agents and hybridization assay probes.

  本文描述了制备式（A）的外消旋和光学活性核苷类似物的过程。这些化合物可用作抗感染剂，反义治疗剂和杂交检测探针。
• 1,5-Anhydro-2-Deoxy-D-Altritol Oligonucleotides as Conformationally Restricted Analogues of Rna
  作者：Brigitte Allart、Arthur Van Aerschot、Piet Herdewijn

  DOI：10.1080/07328319808004682

  日期：1998.9

  As part of a project concerning the investigation of new hexitol nucleic acids (HNA), the 1,5-anhydro-2-deoxy-D-altritol nucleoside building blacks with a uracil, cytosine, adenine and guanine base moiety were synthesized. The uracil analogue was used for the automated synthesis of corresponding oligonucleotides. Hybridization capabilities of these altritol nucleic acids (ANA) are illustrated by the Tm values obtained for the (a(h)U)(13)/(dA)(13) duplex.
• [EN] METHOD OF PREPARATION OF NOVEL NUCLEOSIDE ANALOGS AND USES<br/>[FR] PROCEDE POUR PREPARER DE NOUVEAUX ANALOGUES DE NUCLEOSIDE, ET LEURS UTILISATIONS
  申请人：AUSPEX PHARMACEUTICALS INC

  公开号：WO2005049582A1

  公开（公告）日：2005-06-02

  Processes for the preparation of racemic and optically active nucleoside analogs of formula (A) are described. These compounds are useful as anti-infective agents, antisense therapeutic agents and hybridization assay probes.

  描述了制备式(A)的外消旋和光学活性核苷类似物的过程。这些化合物可用作抗感染剂、反义治疗剂和杂交分析探针。
• Synthesis and antiviral activity of 2-deoxy-1,5-anhydro-D-mannitol nucleosides containing a pyrimidine base moiety
  作者：María-Jesús Pérez-Pérez、Erik De Clercq、Piet Herdewijn

  DOI：10.1016/s0960-894x(96)00244-2

  日期：1996.7

  Nucleoside analogues containing a 2-deoxy-1,5-anhydro-D-mannitol and a pyrimidine base moiety were synthesized starting from D-glucose via a nucleophilic opening of an epoxide with the heterocyclic base and an inversion of configuration at the 3'-position. Study of the conformation of these molecules, that show some activity against herpesviruses (HSV, VZV, CMV) should increase our understanding of the structural requirements of hexitol nucleosides for antiviral activity. Copyright (C) 1996 Elsevier Science Ltd