3'-deoxy-3',4'-didehydrocytidine | 386264-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-deoxy-3',4'-didehydrocytidine
• 英文别名: ddhC；3',4'-Didehydro-3'-deoxycytidine；4-amino-1-[(2R,3R)-3-hydroxy-5-(hydroxymethyl)-2,3-dihydrofuran-2-yl]pyrimidin-2-one
• CAS: 386264-46-6
• 化学式: C₉H₁₁N₃O₄
• 分子量: 225.204
• InChiKey: VQMYKNBUURJYAP-HTRCEHHLSA-N

物化性质

• 沸点：
  516.3±60.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3',4'-didehydrocytidine 在 吡啶 作用下， 生成 1-<2-O-acetyl-5-O-(tert-butyldiphenylsilyl)-β-D-glycero-pent-3-enofuranosyl>-N⁴-acetylcytosine
  参考文献：
  名称：

  Allylic Substitution of 3‘,4‘-Unsaturated Nucleosides:  Organosilicon-Based Stereoselective Access to 4‘-C-Branched 2‘,3‘-Didehydro-2‘,3‘-dideoxyribonucleosides

  摘要：

  Reactions of organosilicon reagents (such as allyltrimethylsilane, silyl enol ethers, cyanotrimethylsilane) with 3',4'-unsaturated nucleosides (of uracil, N-4-acetylcytosine, and hypoxanthine) having an allyl ester structure were investigated in the presence of a Lewis acid in CH2Cl2. In the cases of uracil and N-4-acetylcytosine derivatives, SnCl4 appeared to be suitable, whereas the use of EtAlCl(2) was necessary for the hypoxanthine derivatives. The main pathway of these reactions was found to be a-face-selective S(N)2' allylic substitution, irrespective of the configuration of 2'-0-acyl leaving group. As a result, a new stereoselective operation for C-C bonds formation leading to 4'-carbon-substituted 2',3'-didehydro-2',3'-dideoxyribonucleosides has been disclosed for the first time. Stereochemistry of these 4'-C-branched products can be assigned on the basis of H-1 NMR spectroscopy in terms of the anisotropic shift of H-5 of the pyrimidine base (or H-8 of the hypoxanthine), which is caused by the 5'-0-(tert-butyldiphenylsilyl) protecting group.

  DOI：

  10.1021/jo9516190
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.66h， 生成 3'-deoxy-3',4'-didehydrocytidine
  参考文献：
  名称：

  由DMF二甲基乙缩醛介导的3'-脱氧-3'，4'-二氢核苷的费勒型烯丙基重排：直接进入4'-烷氧基-2'，3'-二氢氢化物2，，3'-二脱氧核苷

  摘要：

  描述了通过DMF二甲基乙缩醛介导的3'-脱氧-3'，4'-二氢核苷的烯丙基重排，直接合成差向异构4'-烷氧基取代的2'，3'-二氢-2'，3'-二氧核苷。

  DOI：

  10.1021/ol201519a

文献信息

• 3’-脱氧-3’,4’-二脱氢核苷类化合物及其应 用
  申请人：成果

  公开号：CN108640959B

  公开（公告）日：2021-01-19

  本发明涉及抗病毒领域，具体涉及核苷类化合物(I)的制备及其在抗HIV病毒、丙肝(HCV)病毒、乙肝(HBV)病毒、狂犬病病毒和寨卡病毒中的应用。本发明的3’-脱氧-3’,4’-二脱氢核苷类化合物在抗病毒中的应用，作为抗病毒的药物，属于首次公开。
• Chemical Synthesis of the Antiviral Nucleotide Analogue ddhCTP
  作者：James M. Wood、Gary B. Evans、Tyler L. Grove、Steven C. Almo、Scott A. Cameron、Richard H. Furneaux、Lawrence D. Harris

  DOI：10.1021/acs.joc.1c00761

  日期：2021.7.2

  (ddhCTP) is a novel antiviral molecule produced by the enzyme viperin as part of the innate immune response. ddhCTP has been shown to act as an obligate chain terminator of flavivirus and SARS-CoV-2 RNA-dependent RNA polymerases; however, further biophysical studies have been precluded by limited access to this promising antiviral. Herein, we report a robust and scalable synthesis of ddhCTP as well as

  3'-Deoxy-3',4'-didehydro-cytidine triphosphate (ddhCTP) 是一种新型抗病毒分子，由 viperin 酶产生，是先天免疫反应的一部分。ddhCTP 已被证明可作为黄病毒和 SARS-CoV-2 RNA 依赖性 RNA 聚合酶的专性链终止子；然而，由于获得这种有前途的抗病毒药物的机会有限，进一步的生物物理学研究被排除在外。在这里，我们分别报告了 ddhCTP 以及单磷酸盐和二磷酸盐 ddhCMP 和 ddhCDP 的稳健且可扩展的合成。2'-甲硅烷基醚保护策略的鉴定使 5'-三磷酸盐的选择性合成和简单纯化成为可能，最终以克级制备 ddhCTP。
• [EN] 2-HYDROXYIMINOPYRIMIDINE NUCLEOSIDES AND DERIVITIVES AND ANTIVIRAL USES THERETO<br/>[FR] NUCLÉOSIDES ET DÉRIVÉS DE 2-HYDROXYIMINOPYRIMIDINE ET UTILISATIONS ANTIVIRALES DE CEUX-CI
  申请人：SINCE & TECH DEVELOPMENT FUND AUTHORITY

  公开号：WO2022008025A1

  公开（公告）日：2022-01-13

  Disclosed herein are nucleosides and nucleotides analogs, methods for preparing the same, and methods for treating and/or ameliorating infection caused by a Coronaviridae virus, a Caliciviridae virus, an Orthomyxoviridae virus, a Herpesviridae virus, a Flaviviridae virus, a Filoviridae virus,and a Pneumoviridae virus with one or more nucleoside and nucleotide analogs of formula I. In certain embodiments, compounds and compositions of nucleoside or nucleotide derivatives are disclosed, which can be administered either alone or in combination with other anti-viral agents. In certain embodiments, the compounds are according to Formula (I): or a pharmaceutically acceptable salt, solvate, stereoisomeric form, a tautomeric form or polymorphic form thereof, wherein R1, R2, R3, R4, X, and sugar are as described herein.

  本文披露了核苷和核苷酸类似物，制备它们的方法，以及使用一种或多种公式I的核苷和核苷酸类似物治疗和/或改善由冠状病毒科病毒、钙病毒科病毒、流感病毒科病毒、疱疹病毒科病毒、黄病毒科病毒、丝状病毒科病毒和肺病毒科病毒引起的感染的方法。在某些实施例中，披露了核苷或核苷酸衍生物的化合物和组成物，可以单独或与其他抗病毒药物组合给予。在某些实施例中，化合物符合以下公式(I)：或其药用可接受的盐、溶剂化合物、立体异构体形式、互变异构体形式或多形形式，其中R1、R2、R3、R4、X和糖如本文所述。
• [EN] PROTECTED DEOXYDIDEHYDRO-NUCLEOSIDES<br/>[FR] DÉSOXYDIDÉHYDRO-NUCLÉOSIDES PROTÉGÉS
  申请人：VICTORIA LINK LTD

  公开号：WO2022123501A1

  公开（公告）日：2022-06-16

  The invention provides compounds of the Formula (I) or the Formula (Ia) which are useful intermediates in the synthesis of potential antiviral drugs such as 3'-deoxy-3',4'-didehydro-cytidine triphosphate (ddhCTP).

  本发明提供了式(I)或式(Ia)的化合物，这些化合物在合成潜在的抗病毒药物，如3'-去氧-3',4'-二脱氢胞嘧啶三磷酸（ddhCTP）中是有用的中间体。
• METHOD FOR DETECTING SLE
  申请人：Keio University

  公开号：EP3904872A1

  公开（公告）日：2021-11-03

  An object of the present invention is to provide a method capable of detecting whether a subject has systemic lupus erythematosus (preferably nephrotic syndrome) with high accuracy without performing a renal biopsy, a biomarker for carrying out such detection, and the like. The concentration of 3',4'-didehydro-3'-deoxycytidine in urine collected from a test subject is measured, and this concentration is compared with a reference concentration for control, which allows to detect whether the above-mentioned test subject has systemic lupus erythematosus (preferably lupus nephritis) with high accuracy.

  本发明的目的是提供一种无需进行肾活检即可高精度检测受试者是否患有系统性红斑狼疮（最好是肾病综合征）的方法、一种用于进行此类检测的生物标记物等。测量从试验对象处收集的尿液中 3',4'-双脱氢-3'-脱氧胞苷的浓度，并将该浓度与对照组的参考浓度进行比较，从而高精度地检测上述试验对象是否患有系统性红斑狼疮（最好是狼疮肾炎）。