5-formyl-1,3-phenylene bis(trifluoromethanesulfonate) | 871345-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-formyl-1,3-phenylene bis(trifluoromethanesulfonate)
• 英文别名: [3-formyl-5-(trifluoromethylsulfonyloxy)phenyl] trifluoromethanesulfonate
• CAS: 871345-33-4
• 化学式: C₉H₄F₆O₇S₂
• 分子量: 402.249
• InChiKey: RQUGTSZNPACDFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5-formyl-1,3-phenylene bis(trifluoromethanesulfonate) 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 3-ethynyl-5-hydroxybenzaldehyde
  参考文献：
  名称：

  [EN] TRIORTHOGONAL REAGENTS FOR DUAL PROTEIN CONJUGATION
  [FR] RÉACTIFS TRIORTHOGONAUX POUR LA CONJUGAISON DE PROTÉINES MIXTES

  摘要：

  本发明涉及三正交试剂，用于在蛋白质上特异性地修饰具有两个正交基团的蛋白质，这些基团随后可以在单一的一锅程序中进行官能化。这种方法依赖于含有附加的法尼醇转移酶或戈氏醇转移酶I底物序列的蛋白质的选择性标记。将双功能乙炔基-羟基苯甲醛并入法尼醇或戈氏醇基团有助于轻松地用两种不同的基团标记蛋白质。

  公开号：

  WO2015057863A1
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 5-formyl-1,3-phenylene bis(trifluoromethanesulfonate)
  参考文献：
  名称：

  1α,25-二羟基维生素 D3 的新型去 C 环和芳香族 D 环类似物的设计、合成、生物活性和结构分析

  摘要：

  天然激素 1α,25-二羟基维生素 D 3 (1,25D 3 , 1,25-二羟基胆钙化醇) 在治疗过度增殖性疾病中的毒性钙化作用需要开发高活性和非钙化维生素 D 类似物。我们报告了 1,25D 3的两种高活性和非钙化类似物的开发，它们缺乏 C 环并具有取代天然 D 环的间苯环。新的类似物 ( 3a , 3b ) 的特征在于附加的六碳羟基化侧链连接到芳环或三烯系统。两种化合物均通过 Pd 催化的串联环化/交叉偶联方法从炔烃开始合成6和联苯酚8。关键步骤包括立体选择性 Cu 辅助将格氏试剂添加到芳族炔烃和芳族醛的 Takai 烯化。新化合物不含钙，并显示出与 1,25D 3相似的转录和抗增殖活性。结构分析表明，它们诱导螺旋 6 周围的维生素 D 受体发生大的构象重排。

  DOI：

  10.1021/acs.jmedchem.2c00900

文献信息

• VITAMIN D ANALOGUES OF PHARMACEUTICAL INTEREST
  申请人：UNIVERSITY DE SANTIAGO DE COMPOSTELA

  公开号：US20160297731A1

  公开（公告）日：2016-10-13

  The present invention relates to compounds of pharmaceutical interest. More particularly, it relates to compounds of formula (I), to processes for obtaining thereof, to the intermediates of their synthesis and processes for obtaining the latter. The compounds of formula (I) have a certain affinity with the vitamin D receptor, they are active in a similar order to 1,25α-dihydroxyvitamin D 3 (1,25D), with the advantage of producing less or no hypercalcemia.

  本发明涉及具有药用兴趣的化合物。更具体地说，它涉及具有式(I)的化合物，其获得方法，其合成的中间体以及获得后者的方法。式(I)的化合物与维生素D受体具有一定的亲和力，它们的活性与1,25α-二羟基维生素D3(1,25D)相似，具有产生较少或无高钙血症的优点。
• TRIORTHOGONAL REAGENTS FOR DUAL PROTEIN CONJUGATION
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US20160271261A1

  公开（公告）日：2016-09-22

  The present invention relates to triorthogonal reagents useful for site-specifically modifying a protein with two orthogonal groups that can be subsequently functionalized in a single one-pot procedure. This approach relies on the selective tagging of proteins containing an appended farnesyltransferase or geranylgeranyltransferase I substrate sequence. The incorporation of a bifunctional ethynyl-hydroxybenzaldehyde into the farnesyl or geranylgeranyl group facilitates the facile labeling of proteins with two different moieties.

  本发明涉及三正交试剂，用于在蛋白质中特异性地修饰两个正交基团，随后可以在单一一锅法中进行功能化。这种方法依赖于选择性地标记含有附加法尼酰转移酶或戊二烯基转移酶I底物序列的蛋白质。将双功能乙炔基-羟基苯甲醛并入法尼酰或戊二烯基基团中，有助于轻松地用两种不同的基团标记蛋白质。
• Selective and orally bioavailable phenylglycine tissue factor/factor VIIa inhibitors
  作者：Katrin Groebke Zbinden、Ulrike Obst-Sander、Kurt Hilpert、Holger Kühne、David W. Banner、Hans-Joachim Böhm、Martin Stahl、Jean Ackermann、Leo Alig、Lutz Weber、Hans Peter Wessel、Markus A. Riederer、Thomas B. Tschopp、Thierry Lavé

  DOI：10.1016/j.bmcl.2005.04.079

  日期：2005.12

  We describe the structure-based design and synthesis of highly potent, orally bioavailable tissue factor/factor Vila inhibitors which interfere with the coagulation cascade by selective inhibition of the extrinsic pathway. (c) 2005 Elsevier Ltd. All rights reserved.
• Simultaneous Dual Protein Labeling Using a Triorthogonal Reagent
  作者：Mohammad Rashidian、Sidath C. Kumarapperuma、Kari Gabrielse、Adrian Fegan、Carston R. Wagner、Mark D. Distefano

  DOI：10.1021/ja403813b

  日期：2013.11.6

  Construction of heterofunctional proteins is a rapidly emerging area of biotherapeutics. Combining a protein with other moieties, such as a targeting element, a toxic protein or small molecule, and a fluorophore or polyethylene glycol (PEG) group, can improve the specificity, functionality, potency, and pharmacokinetic profile of a protein. Protein farnesyl transferase (PFTase) is able to site-specifically and quantitatively prenylate proteins containing a C-terminal CaaX-box amino acid sequence with various modified isoprenoids. Here, we describe the design, synthesis, and application of a triorthogonal reagent, 1, that can be used to site-specifically incorporate an alkyne and aldehyde group simultaneously into a protein. To illustrate the capabilities of this approach, a protein was enzymatically modified with compound 1 followed by oxime ligation and click reaction to simultaneously incorporate an azido-tetramethylrhodamine (TAMRA) fluorophore and an aminooxy-PEG moiety. This was performed with both a model protein [green fluorescent protein (GFP)] as well as a therapeutically useful protein [ciliary neurotrophic factor (CNTF)]. Next, a protein was enzymatically modified with compound 1 followed by coupling to an azido-bis-methotrexate dimerizer and aminooxy-TAMRA. Incubation of that construct with a dihydrofolate reductase (DHFR)-DHFR-anti-CD3 fusion protein resulted in the self-assembly of nanoring structures that were endocytosed into T-leukemia cells and visualized therein. These results highlight how complex multifunctional protein assemblies can be prepared using this facile triorthogonal approach.
• US9663429B2
  申请人：——

  公开号：US9663429B2

  公开（公告）日：2017-05-30