3'-deoxy-3'-nitrothymidine | 151753-97-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-deoxy-3'-nitrothymidine
• 英文别名: 1-[(2R,4S,5S)-5-(hydroxymethyl)-4-nitro-tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,4S,5S)-5-(hydroxymethyl)-4-nitrooxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 151753-97-8
• 化学式: C₁₀H₁₃N₃O₆
• 分子量: 271.23
• InChiKey: STLCSWMENRFYNO-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-nitrothymidine 在 sodium carbonate 作用下， 反应 1.0h， 以100%的产率得到1-(2,3-dideoxy-3-nitronate-β-D-glycero-pentofuranosyl)thymine sodium salt
  参考文献：
  名称：

  新型3'-C / N-取代的2'，3'-β-D-二脱氧核苷作为潜在的化学治疗剂。1.胸苷衍生物：合成，结构和广谱抗病毒特性。

  摘要：

  1-（2,3-二脱氧-β-D-甘油-戊呋喃糖基）胸腺嘧啶的3'-肟衍生物3E，5E，5Z，7E和7Z和1-（2,3-二脱氧-3）的合成方案从适当的5'-保护的3'-酮基吡啶开始开发了-硝基-β-D-赤型-五氟呋喃糖基）-胸腺嘧啶（10）。X射线分析表明3'-N-羟基亚氨基3E和3'-N-甲氧基亚氨基5Z衍生物具有紧密的分子构象：抗N1-C1'键，和gauche +抗C4'-C5'环外键。它们的糖构象分别为C1'-exo-O4'-endo和C1'-exo-C2'-endo。细胞培养物中的抗病毒测定表明3'-N-羟基亚氨基3E和3'-N-乙酰氧基亚氨基7E + 7Z衍生物具有抗人免疫缺陷病毒（HIV）的显着活性，EC50值在0.02和0之间。HIV-1和HIV-2均为40微克/ mL。其他化合物5E + 5Z和10的活性降低至少2个数量级。3'-N-羟基亚氨基衍生物3E还显示出抗乙肝病毒（HBV）（EC50

  DOI：

  10.1021/jm960500w
• 作为产物：
  描述：

  1-(2,3-dideoxy-3-nitro-5-O-trityl-β-D-erythro-pentofuranosyl)-2-methoxy-5-methyl-4(1H)-pyrimidinone 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以30%的产率得到3'-deoxy-3'-nitrothymidine
  参考文献：
  名称：

  3'-脱氧-3'- nitrothymidine的一种新颖的合成通过与亚硝酸根阴离子的亲核取代

  摘要：

  1-（2-脱氧-5- O-三苯甲基-β-D-季戊基-呋喃呋喃糖基）-2-甲氧基-5-甲基-4（1 H）-嘧啶酮（5）在C3'处的亲核取代为甲基碘/三苯基膦/偶氮二羧酸二乙酯给出了预期的倒碘化物6和次要差向异构体7。用亚硝酸锂/间苯三酚处理6得到所需的硝基衍生物8，然后进行酸性脱保护得到标题化合物1。这代表了将硝基引入核苷的呋喃糖基部分的新方法。使用核磁共振光谱技术（COSY，NOESY，nOe，HMQC和HMBC）确定核苷C3'的立体化学。在1的3'-位置进行HD交换的光谱分析未显示其差向异构体10的形成。

  DOI：

  10.1002/jhet.5570320253

文献信息

• Nucleoside analog inhibitors of reverse transcriptase
  申请人：——

  公开号：US20040235869A1

  公开（公告）日：2004-11-25

  Compounds of formula (XXIII), or pharmaceutically acceptable salts or esters thereof, are inhibitors of reverse transcriptase: 1 R 4 is a nucleoside with Q substituting a 3′ hydroxyl group, and Q is a moiety of formulas (XXIV)-(XXXII): 2

  公式（XXIII）的化合物，或其药学上可接受的盐或酯，是反转录酶的抑制剂：1R4是一种核苷，其中Q替代3'羟基，Q是公式（XXIV）-（XXXII）的一个部分。
• Electronic detection of interaction and detection of interaction based on the interruption of flow
  申请人：——

  公开号：US20020098526A1

  公开（公告）日：2002-07-25

  Porous members can be positioned so as to partially or fully span channels in microfluidic systems. The porous members can be assembled and/or disassembled in situ. The porous members can be made such that pores are separated by connections including but a single molecule at one location, allowing for a high level of open area in a very small pore size member. The porous member can be made up of colloid particles interconnected with molecular species. These can be used to detect analytes qualitatively and/or quantitatively, or to selectively bind and/or release agents on command for a variety of purposes including first blocking, then opening a channel, concentrating analyte over time followed by release of analyte and detection downstream, etc. Porous members can define valves in multiple-channel systems and, with controlled binding and release of agents at the porous members, these valves can be opened and closed and fluid flow controlled in a multi-channel system. Fluidic systems of the invention can include multiple sensing locations at which different analytes are determined. Systems of the invention provide flexibility for overall microchemical analysis, sequentially, of a variety of agents.

  多孔部件可以定位，以便部分或全部跨过微流体系统中的通道。多孔部件可在原位组装和/或拆卸。多孔构件可以通过连接来分隔孔隙，但在一个位置上只包括一个分子，这样就能在一个孔径很小的构件中实现较大的开放面积。多孔部件可以由与分子物种相互连接的胶体颗粒组成。这些颗粒可用于定性和/或定量检测分析物，或根据指令选择性地结合和/或释放药剂，以达到各种目的，包括首先阻塞，然后打开通道，随着时间的推移浓缩分析物，然后释放分析物并进行下游检测等。多孔部件可以在多通道系统中定义阀门，通过控制多孔部件上的药剂结合和释放，可以在多通道系统中打开和关闭这些阀门并控制流体流动。本发明的流体系统可包括多个传感位置，在这些位置可测定不同的分析物。本发明的系统可灵活地按顺序对各种药剂进行整体微化学分析。
• ELECTRONIC DETECTION OF INTERACTION AND DETECTION OF INTERACTION BASED ON THE INTERRUPTION OF FLOW
  申请人：Minerva Biotechnologies Corporation

  公开号：EP1381440A2

  公开（公告）日：2004-01-21
• MINIATURIZED PRESSURE DROP FILTER AND METHODS OF USING IT
  申请人：Minerva Biotechnologies Corporation

  公开号：EP1381440B1

  公开（公告）日：2013-01-30
• ELECTRONIC DETECTION OF INTERACTION AND DETECTION OF INTERACTION BASED ON THE INTERRUPTION FLOW
  申请人：BAMDAD Cynthia C.

  公开号：US20100124789A1

  公开（公告）日：2010-05-20

  Porous members can be positioned so as to partially or fully span channels in microfluidic systems. The porous members can be assembled and/or disassembled in situ. The porous members can be made such that pores are separated by connections including but a single molecule at one location, allowing for a high level of open area in a very small pore size member. The porous member can be made up of colloid particles interconnected with molecular species. These can be used to detect analytes qualitatively and/or quantitatively, or to selectively bind and/or release agents on command for a variety of purposes including first blocking, then opening a channel, concentrating analyte over time followed by release of analyte and detection downstream, etc. Porous members can define valves in multiple-channel systems and, with controlled binding and release of agents at the porous members, these valves can be opened and closed and fluid flow controlled in a multi-channel system. Fluidic systems of the invention can include multiple sensing locations at which different analytes are determined. Systems of the invention provide flexibility for overall microchemical analysis, sequentially, of a variety of agents.