dapoxylsulfonyl chloride | 138219-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dapoxylsulfonyl chloride
• 英文别名: dapoxyl chloride；Benzenesulfonyl chloride, 4-[5-[4-(dimethylamino)phenyl]-2-oxazolyl]-；4-[5-[4-(dimethylamino)phenyl]-1,3-oxazol-2-yl]benzenesulfonyl chloride
• CAS: 138219-55-3
• 化学式: C₁₇H₁₅ClN₂O₃S
• 分子量: 362.837
• InChiKey: CEFCZUDGNCOQCM-UHFFFAOYSA-N

物化性质

• 沸点：
  533.6±60.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dapoxylsulfonyl chloride 在 氨 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以65%的产率得到4-(5-dimethylaminophenyl-2-oxazolyl)benzenesulfonamide
  参考文献：
  名称：

  4-(5-aryl-2-oxazolyl)benzenesulfonic acid derivatives containing a dimethylamino group

  摘要：

  DOI：

  10.1007/bf00531666
• 作为产物：
  描述：

  4-(氯磺酰基)苯甲酰氯 在 碳酸氢钠 、 三氯氧磷 作用下， 以 水 、 苯 为溶剂， 反应 3.0h， 生成 dapoxylsulfonyl chloride
  参考文献：
  名称：

  4-(5-aryl-2-oxazolyl)benzenesulfonic acid derivatives containing a dimethylamino group

  摘要：

  DOI：

  10.1007/bf00531666

文献信息

• Substituted diphenyloxazoles, the synthesis thereof, and the use thereof as fluorescence probes
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US20030105111A1

  公开（公告）日：2003-06-05

  The present invention is directed to a compound of Formula I: 1 wherein A, R 1 , and R 2 are defined herein. The present invention is also directed to compositions comprising compounds of Formula I, methods of using compounds of Formula I, and methods of making compounds of Formula I.

  本发明涉及一种具有以下结构的化合物：其中A、R1和R2在此处被定义。本发明还涉及包含Formula I化合物的组合物、使用Formula I化合物的方法以及制备Formula I化合物的方法。
• Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols
  作者：Peter Greimel、Herwig Häusler、Inge Lundt、Karen Rupitz、Arnold E. Stütz、Chris A. Tarling、Stephen G. Withers、Tanja M. Wrodnigg

  DOI：10.1016/j.bmcl.2006.01.095

  日期：2006.4

  1,5-Dideoxy-1,5-iminoalditols of various configurations as well as isofagomine were N-alkylated with non-polar straight chain spacer-arms by a set of simple standard procedures. The spacer-arms' terminal functional groups, primary amines, were employed to introduce fluorescent tags such as dansyl and dapoxyl moieties. Resulting derivatives in the D-xylo, D-gluco, D-galacto as well as GlcNAc series showed distinctly improved glycosidase inhibitory activities compared to parent compounds and are designed to be useful analytical tools. (C) 2006 Elsevier Ltd. All rights reserved.
• Development of Molecular Probes for the Human 5-HT₆ Receptor
  作者：Henar Vázquez-Villa、Juan A. González-Vera、Bellinda Benhamú、Alma Viso、Roberto Fernández de la Pradilla、Elena Junquera、Emilio Aicart、María L. López-Rodríguez、Silvia Ortega-Gutiérrez

  DOI：10.1021/jm1007177

  日期：2010.10.14

  In this work we report the synthesis of a set of labeled ligands targeting the human 5-HT6, receptor (h5-HT6R). Among the synthesized compounds, fluorescent probe 10 (K-i = 175 nM and Phi(f) = 0.21 and biotinylated derivative 15 (K-i = 90 nM) deserve special attention because they enable direct observation of the h5-HT6R in cells. Thus, they represent the first molecular probes for 5-HT6R visualization. These results are the starting point for introducing a variety of tags in these or other 5-HT6R ligand scaffolds aimed at the development of optimized probes with tailored profiles in terms of fluorescence, affinity, or selectivity.
• Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity
  作者：Matilde Aguilar-Moncayo、M. Isabel García-Moreno、Arnold E. Stütz、José M. García Fernández、Tanja M. Wrodnigg、Carmen Ortiz Mellet

  DOI：10.1016/j.bmc.2010.09.003

  日期：2010.11

  New fluorescently-labelled sp(2)-iminosugars based on the 5N,6S-[N'-(4-aminobutyl)iminomethylidene]-6-thionojirimycin skeleton have been synthesized as photoprobes to monitor glycosidase binding. Dansyl, dapoxyl and coumarin fluorophores were appended to the terminal amino group at the N'-substituent by either sulfonamide or amide bridging reaction. All the conjugates behaved as strong (low micromolar to nanomolar) and selective inhibitors of beta-glucosidases (almonds and bovine liver) and naringinase, in agreement with the inhibition pattern previously encountered for related iso(thio)urea-type bicyclic sp(2)-iminosugars. The presence of the fluorescent probe allows real-time and continuous monitoring of beta-glucosidase inhibition by fluorescence resonance energy transfer (FRET), taking advantage of the intrinsic tryptophan-associated fluorescence of the protein. (C) 2010 Elsevier Ltd. All rights reserved.
• Fluorescent Molecular Probes II. The Synthesis, Spectral Properties and Use of Fluorescent Solvatochromic Dapoxyl Dyes
  作者：Zhenjun Diwu、Yixin Lu、Cailan Zhang、Dieter H. Klaubert、Richard P. Haugland

  DOI：10.1111/j.1751-1097.1997.tb03168.x

  日期：1997.10

  Abstract— 2,5‐Diphenyloxazoles that embody a dimethylamino group at position 4 of the 5‐phenyl ring and a sulfonyl group at position 4 of the 2‐phenyl ring were prepared as new fluorescent solvatochromic dyes. In these molecules, there is a “push‐pull” electron transfer system from the 5‐phenyl moiety to the 2‐phenyl ring. These compounds show strong solvent‐dependent fluorescence that is well correlated with the empirical solvent polarity parameter ET (30). The solvent polarity dependence suggests that the fluorescence arises from an intramolecular charge transfer. The fluorescence‐environment dependence, long emission wavelength, large extinction coefficients, high fluorescence quantum yields and large Stokes shift of the fluorophores can be used to develop ultrasensitive fluorescent molecular probes to study a variety of biological events and processes.