3-(2',3'-dideoxy-ribo-β-L-furanosyl)-6-(n-nonyl)furo[2,3-d]pyrimidin-2(3H)-one | 1417901-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 3-(2',3'-dideoxy-ribo-β-L-furanosyl)-6-(n-nonyl)furo[2,3-d]pyrimidin-2(3H)-one
• 英文别名: 3-(2',3'-dideoxy-ribo-β-L-furanosyl)-6-nonylfuro[2,3-d]pyrimidin-2(3H)-one；Cf 3175；Cf3175；3-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]-6-nonylfuro[2,3-d]pyrimidin-2-one
• CAS: 1417901-82-6
• 化学式: C₂₀H₃₀N₂O₄
• 分子量: 362.469
• InChiKey: IQKXBKDHCXQKLM-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5′,3′-diacetyl-2′-bromo-2′-deoxyuridine 在 copper(l) iodide 、 四(三苯基膦)钯 、 ammonium cerium (IV) nitrate 、 palladium 10% on activated carbon 、 氢气 、 碘 、 sodium methylate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 锌 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 55.0h， 生成 3-(2',3'-dideoxy-ribo-β-L-furanosyl)-6-(n-nonyl)furo[2,3-d]pyrimidin-2(3H)-one
  参考文献：
  名称：

  Novel Antiviral Activity of l-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro

  摘要：

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.

  DOI：

  10.1021/jm301778x

文献信息

• [EN] CONDENSED PYRIMIDINE NUCLEOSIDE ANALOGS AS ANTI -VIRAL AGENTS<br/>[FR] ANALOGUES DE NUCLÉOSIDES DE PYRIMIDINE CONDENSÉS EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UNIV CARDIFF

  公开号：WO2013007992A1

  公开（公告）日：2013-01-17

  3-(2',3'-dideoxy-ribo-β-L-furanosyl)[2,3-d]pyrimidin-2(3H)-one derivatives comprising 6-substitutents on the base moiety are shown to have anti-viral properties, particularly with respect to vaccinia and measles. The compounds have unnatural L ribose stereochemistry.

  已知在嘌呤碱基部分具有6-取代基的3-(2',3'-二去氧-β-L-呋喃核苷基)[2,3-d]嘧啶-2(3H)-酮衍生物具有抗病毒性能，特别是针对天花病毒和麻疹病毒。这些化合物具有非天然的L核糖立体化学结构。
• CHEMICAL COMPOUNDS
  申请人：McGuigan Christopher

  公开号：US20130012468A1

  公开（公告）日：2013-01-10

  3-(2′,3′-dideoxy-ribo-β-L-furanosyl)[2,3-d]pyrimidin-2(3H)-one derivatives comprising 6-substitutents on the base moiety are shown to have anti-viral properties, particularly with respect to vaccinia and measles. The compounds have unnatural L ribose stereochemistry.

  在碱基部分上含有6-取代基的3-(2′,3′-二脱氧-β-L-呋喃核糖基)[2,3-d]嘧啶-2(3H)-酮衍生物显示出抗病毒特性，特别是对天花病毒和麻疹病毒。这些化合物具有非自然的L-核糖立体化学结构。
• CONDENSED PYRIMIDINE NUCLEOSIDE ANALOGS AS ANTI-VIRAL AGENTS
  申请人：University College Cardiff Consultants, Ltd.

  公开号：EP2729153B1

  公开（公告）日：2015-09-16
• US8551966B2
  申请人：——

  公开号：US8551966B2

  公开（公告）日：2013-10-08
• Novel Antiviral Activity of <scp>l</scp>-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro
  作者：Christopher McGuigan、Karen Hinsinger、Laura Farleigh、Ranjith N. Pathirana、Joachim J. Bugert

  DOI：10.1021/jm301778x

  日期：2013.2.14

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.