4-nitrophenyl cyanoformate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-nitrophenyl cyanoformate
• 英文别名: p-Nitrophenyl cyanoformate；(4-nitrophenyl) cyanoformate
• 化学式: C₈H₄N₂O₄
• 分子量: 192.131
• InChiKey: ZHUJIPMQASOJDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(叠氮甲基)噻吩 、 4-nitrophenyl cyanoformate 反应 16.0h， 生成 (4-Nitrophenyl) 1-(thiophen-2-ylmethyl)tetrazole-5-carboxylate
  参考文献：
  名称：

  Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

  摘要：

  Alpha-dystroglycan (alpha-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of alpha-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of alpha-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of alpha-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of alpha-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of alpha-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of alpha-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.011
• 作为产物：
  描述：

  三甲基氰硅烷 、 对硝基苯基氯甲酸酯 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以47%的产率得到4-nitrophenyl cyanoformate
  参考文献：
  名称：

  Small-compound enhancers for functional O-mannosylation of alpha-dystroglycan, and uses thereof

  摘要：

  本发明提供了一种可以增强蛋白质的O-甘露糖基化功能，包括α-骨骼肌糖蛋白的化合物。还提供了一种按照式I定义的化合物的制备方法。同时提供了使用这些化合物或其药用可接受的盐或前药来治疗和预防患有包括肌肉萎缩症和癌症在内的疾病的方法。

  公开号：

  US10221168B1

文献信息

• Method for producing pyridine derivatives
  申请人：KURARAY CO., LTD.

  公开号：US20010031871A1

  公开（公告）日：2001-10-18

  A pyridine alcohol derivative represented by General Formula III 1 (where A represents a divalent organic group which may contain one to three oxygen atoms, nitrogen atoms and/or sulfur atoms, wherein A may form a 5-, 6-, 7-, or 8-membered ring together with two bonded carbon atoms, where said ring may form a condensed ring with one or more additional rings; R 5 represents a hydrogen atom, —CHR 1 R 2 , or an alkenyl group, an aryl group or an aralkyl group which may be substituted; R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group which may be substituted; and R 6 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or an aralkyl group which may be substituted), is produced by: reacting a pyridine ester derivative represented by General Formula I-1 2 (where Z 1 represents —COX; X represents an alkoxyl group, an alkenyloxy group, an aryloxy group or an aralkyloxy group which may be substituted; and A is the same as above) with-a reducing agent, an alkylating agent, an alkenylating agent, an arylating agent or an aralkylating agent to obtain a pyridine carbonyl derivative represented by General Formula II 3 (where A and R are the same as above); and reacting the resulting pyridine carbonyl derivative with a reducing agent, an alkylating agent, an alkenylating agent, an arylating agent or an aralkylating agent to obtain the pyridine alcohol derivative of the General Formula III.

  一种由通式III1表示的吡啶醇衍生物（其中A表示一个双价有机基团，该基团可以含有一个到三个氧原子、氮原子和/或硫原子，其中A可以与两个键合的碳原子一起形成一个5、6、7或8元环，其中该环可以与一个或多个附加环形成紧缩环；R5表示氢原子、—CHR1R2或可以被取代的烯基基团、芳基基团或芳基烷基基团；R1和R2分别独立地表示氢原子或可以被取代的碳氢基团；R6表示氢原子、烷基基团、烯基基团、芳基基团或芳基烷基基团，可以被取代），通过以下步骤制备：将由通式I-12表示的吡啶酯衍生物（其中Z1表示—COX；X表示可以被取代的烷氧基团、烯基氧基团、芳基氧基团或芳基烷氧基团；A与上述相同）与还原剂、烷基化试剂、烯基化试剂、芳基化试剂或芳基烷基化试剂反应，得到由通式II3表示的吡啶羰基衍生物（其中A和R与上述相同）；并将所得的吡啶羰基衍生物与还原剂、烷基化试剂、烯基化试剂、芳基化试剂或芳基烷基化试剂反应，得到通式III的吡啶醇衍生物。
• A Click Chemistry Approach to Tetrazoles by Huisgen 1,3-Dipolar Cycloaddition: Synthesis of 5-Acyltetrazoles from Azides and Acyl Cyanides We thank the National Institute of General Medical Sciences, National Institutes of Health (GM-28384), the National Science Foundation (CHE-9985553), the Skaggs Institute for Chemical Biology for a Predoctoral Fellowship (Z.D.), and the W. M. Keck Foundation for financial support.
  作者：Zachary P. Demko、K. Barry Sharpless

  DOI：10.1002/1521-3773(20020617)41:12<2113::aid-anie2113>3.0.co;2-q

  日期：2002.6.17
• Method for producing furopyridine derivatives and intermediate compounds
  申请人：Kuraray Co., Ltd.

  公开号：EP0911335B1

  公开（公告）日：2002-04-17
• US6111111A
  申请人：——

  公开号：US6111111A

  公开（公告）日：2000-08-29
• US6265580B1
  申请人：——

  公开号：US6265580B1

  公开（公告）日：2001-07-24