sodium hydroxy(4-(trifluoromethyl)phenyl)methanesulfonate | 152782-75-7

• 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: sodium hydroxy(4-(trifluoromethyl)phenyl)methanesulfonate
• 英文别名: Sodium;hydroxy-[4-(trifluoromethyl)phenyl]methanesulfonate；sodium;hydroxy-[4-(trifluoromethyl)phenyl]methanesulfonate
• CAS: 152782-75-7
• 化学式: C₈H₆F₃O₄S*Na
• 分子量: 278.184
• InChiKey: SOENYTPNOFJOAJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.75
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium hydroxy(4-(trifluoromethyl)phenyl)methanesulfonate 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-(1-(2-(4-trifluoromethylphenyl)-1H-benzimidazol-5-yl)ethylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  5-Acetyl-2-arylbenzimidazoles as antiviral agents. Part 4

  摘要：

  Within a project aimed at discovering new Flaviviridae inhibitors, new variously substituted 2-phenylbenzimidazoles were synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against viruses representatives of the three genera of the Flaviviridae family, i.e.: Pestivirus (BVDV), Flavivirus (YFV) and Hepacivirus (HCV). Title compounds were also tested against RNA viruses representative of other single-stranded, positive-sense (ssRNA(+)) negative-sense (RNA(-)), or double-stranded (dsRNA) genomes, as well as against representatives of two DNA virus families.Nine compounds showed activity against BVDV (EC50 = 0.8-8.0 mu M), compound 31 being the most potent (EC50 = 0.80 mu M) and selective (SI = CC50/EC50 = >100). When tested in an HCV replicon assay, compound 31 resulted again the most potent, displaying an EC50 value of 1.11 mu M and an SI of 100. Besides inhibiting BVDV, two compounds (35 and 38) showed a moderate activity also against YFV (EC50 = 13 mu M). Interestingly, 35 was moderately active also against RSV (EC50 = 25 mu M). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.038
• 作为产物：
  描述：

  对三氟甲基苯甲醛 在 sodium hydrogensulfite 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 sodium hydroxy(4-(trifluoromethyl)phenyl)methanesulfonate
  参考文献：
  名称：

  在室温下用硼氢化镁试剂将Weinreb酰胺还原为醛

  摘要：

  二甲基氨基硼氢化氯镁（ClMg + [H 3 BNMe 2 ] -，MgAB）是通用的二烷基氨基硼氢化锂（LAB试剂）的类似物，它是通过二甲基胺-硼烷与甲基氯化镁的反应制得的。MgAB在环境条件下是Weinreb酰胺的部分还原剂，与常用的氢化铝锂（LiAlH 4）和二异丁基氢化铝（DIBAL）试剂，同时展现出更高的化学选择性。为了防止过度还原，通过形成亚硫酸氢钠加合物容易地以高收率分离醛产物。醛产物既可以储存，也可以随后用作亚硫酸氢盐加合物，或者可以通过用甲醛水溶液处理从亚硫酸氢盐加合物再生。

  DOI：

  10.1016/j.tetlet.2014.12.066

文献信息

• Novel Clarithromycin Analogs with C-4” 2-arylbenzimidazolyl Bishydrazide Side Chain: Synthesis and Antibacterial Evaluation
  作者：Yunkun Qi、Ruixin Ma、Xin Li、Yue Hu、Siti Ma、Chao Cong、Xiaodong Ma、Wenping Cui、Shutao Ma

  DOI：10.2174/157018011797655269

  日期：2011.12.1

  A series of novel 4” -O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4” -O-2-arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4” bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.

  一系列新型的克拉霉素4”-O-2-芳基苯并咪唑衍生物被合成并评估。这些4”-O-2-芳基苯并咪唑衍生物对红霉素敏感菌株显示出优异的活性，并且相较于参考药物，对红霉素耐药菌株的活性显著提高。特别是化合物7c，其在C-4”双酰肼侧链上带有末端的2-（2-甲氧基苯基）苯并咪唑基团，不仅对红霉素敏感的肺炎链球菌ATCC49619和金黄色葡萄球菌ATCC25923表现出最强的活性，效能分别是母体克拉霉素的4倍和4倍，而且对表达mef基因和erm基因的红霉素耐药肺炎链球菌的活性也是最高的，分别是克拉霉素或阿奇霉素的133倍和32倍。
• A combined in silico / in vitro approach unveils common molecular requirements for efficient BVDV RdRp binding of linear aromatic N-polycyclic systems
  作者：A. Carta、I. Briguglio、S. Piras、P. Corona、R. Ibba、E. Laurini、M. Fermeglia、S. Pricl、N. Desideri、E.M. Atzori、P. La Colla、G. Collu、I. Delogu、R. Loddo

  DOI：10.1016/j.ejmech.2016.03.080

  日期：2016.7

  according to which two hydrogen bond acceptors and one hydrophobic aromatic feature are shared by all molecular series in binding the viral polymerase. The pharmacophoric information was used to retrieve a putative binding site on the surface of the BVDV RdRp and to guide compound docking within the protein binding site. The affinity of all compounds towards the enzyme was scored via molecular dynamics-based

  在这项工作中，我们介绍和讨论一整套新的和以前合成的化合物，它们分别属于5个不同的线性芳族N-多环系统分子类别，可有效抑制牛病毒性腹泻病毒（BVDV）感染。耦合的计算机/体外研究人员使用分子生物学原理来解释所有分子对BVDV RNA依赖性RNA聚合酶（RdRp）NS5B的显着亲和力。我们最初开发了三维共有特征的药效团模型，根据该模型，两个分子结合病毒聚合酶时，两个氢键受体和一个疏水性芳香族特征将共享。药效学信息用于检索BVDV RdRp表面上的推定结合位点，并指导化合物对接在蛋白质结合位点内。通过基于分子动力学的模拟对所有化合物对酶的亲和力进行了评分，显示出与体外EC 50的高度相关性数据。确定参与抑制剂结合的蛋白质残基的相互作用谱，突出显示了氨基酸R295和Y674是两个基本的H键供体，而两个疏水腔HC1（残基A221，I261，I287和Y289）和HC2（残基V216） ，Y303，V
• Synthesis and antiviral activity of new phenylimidazopyridines and N-benzylidenequinolinamines derived by molecular simplification of phenylimidazo[4,5-g]quinolines
  作者：Roberta Loddo、Irene Briguglio、Paola Corona、Sandra Piras、Mario Loriga、Giuseppe Paglietti、Antonio Carta、Giuseppina Sanna、Gabriele Giliberti、Cristina Ibba、Pamela Farci、Paolo La Colla

  DOI：10.1016/j.ejmech.2014.07.011

  日期：2014.9

  assays for cytotoxicity and antiviral activity against representatives of two DNA virus families as wells as against representatives of RNA virus families containing single-stranded, either positive-sense (ssRNA+) or negative-sense (ssRNA−), and double-stranded genomes (dsRNA). Some imidazo[4,5-b]pyridines emerged as new derivatives endowed with antiviral activity against Vaccinia Virus (VV) at concentrations

  继续进行有关一系列新的角和线性偶氮双环和三环衍生物的抗病毒活性的研究计划，现在我们简化并修饰了4-氯-2-（4-硝基苯基）-3 H-咪唑[4，通过消除中心环或咪唑环的打开，先前产生活性最高的衍生物的5- g ]喹啉1分别获得各种咪唑并吡啶和N-亚苄基喹啉胺。 标题化合物中的细胞毒性和抗病毒活性对两个DNA病毒科的代表，孔中作为对含有单链，无论是正链（单链RNA的RNA病毒科的代表基于细胞的测定中测试+）或负义单链RNA（-）和双链基因组（dsRNA）。一些咪唑并[4,5- b ]吡啶以新衍生物的形式出现，在2至16μM的浓度范围内具有抗痘苗病毒（VV）的抗病毒活性。特别是，化合物2b的功效比用作参考药物的西多福韦强约10倍。同样，咪唑并[4,5- c ]吡啶和N-亚苄基喹啉胺衍生物在1.2至28μM的浓度范围内具有抗牛病毒性腹泻病毒（BVDV）的活性。所有上述化合物1，图3a和3f中显示出EC
• 一种利用醛亚硫酸氢钠加合物制备4-芳基- NH-1,2,3-三唑的方法
  申请人：海南师范大学

  公开号：CN106146417B

  公开（公告）日：2018-12-04

  本发明涉及一种利用醛亚硫酸氢钠加合物制备4‑芳基‑NH‑1,2,3‑三唑的方法，其特征在于包括如下步骤：醛亚硫酸氢钠加合物、硝基化合物、叠氮化钠、溶剂、添加剂通过“一锅法”于60‑150℃条件下反应1‑10小时，反应结束后，经后处理，可制得4‑芳基‑NH‑1,2,3‑三唑。本发明采用廉价易得的醛亚硫酸氢钠加合物，硝基化合物，叠氮化钠为原料，可以将三组分便捷地制备4‑芳基‑NH‑1,2,3‑三唑类化合物。与已有方法相比，本方法原料价格低廉且简单易得，操作简便，反应效率高。
• Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors
  作者：Yeong Keng Yoon、Mohamed Ashraf Ali、Ang Chee Wei、Tan Soo Choon、Kooi-Yeong Khaw、Vikneswaran Murugaiyah、Hasnah Osman、Vijay H. Masand

  DOI：10.1016/j.bioorg.2013.06.008

  日期：2013.8

  Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by the elemental and mass spectral analyses as well as H-1 NMR spectroscopic data. Of the 34 novel synthesized compounds, three benzimidazoles revealed AChE inhibition with IC50 < 10 mu M. The highest inhibitory activity (IC50 = 5.12 mu M for AChE and IC50 = 8.63 mu M for BChE) corresponds to the compound 5IIc (ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate). The relationship between lipophilicity and the chemical structures as well as their limited structure-activity relationship was discussed. (C) 2013 Elsevier Inc. All rights reserved.