1-prop-2-ynyloxy-4-trifluoromethoxy-benzene | 1268158-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-prop-2-ynyloxy-4-trifluoromethoxy-benzene
• 英文别名: 4-(trifluoromethoxy)propargyloxybenzene；1-(Propargyloxy)-4-(trifluoromethoxy)benzene；1-prop-2-ynoxy-4-(trifluoromethoxy)benzene
• CAS: 1268158-82-2
• 化学式: C₁₀H₇F₃O₂
• 分子量: 216.16
• InChiKey: JKUJWNOFLDYGKR-UHFFFAOYSA-N

物化性质

• 沸点：
  220.3±40.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-叠氮苯酚 、 1-prop-2-ynyloxy-4-trifluoromethoxy-benzene 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 12.0h， 生成 (R)-2-{2-[4-(4-trifluoromethoxyphenoxy)methyl-1H-1,2,3-triazol-1-yl]phenoxymethyl}-2,3-dihydro-2-methyl-6-nitroimidazo[2,1-b]oxazole
  参考文献：
  名称：

  Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: in vitro, structure–activity relationship, pharmacokinetics and in vivo evaluation

  摘要：

  有前途的硝基咪唑噁唑骨架提供了另一种新颖的三唑基含有的6-硝基-2,3-二氢咪唑噁唑作为抗结核病的先导化合物。

  DOI：

  10.1039/c5ob00054h
• 作为产物：
  描述：

  对三氟甲氧基苯酚 、 3-溴丙炔 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-prop-2-ynyloxy-4-trifluoromethoxy-benzene
  参考文献：
  名称：

  Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: in vitro, structure–activity relationship, pharmacokinetics and in vivo evaluation

  摘要：

  有前途的硝基咪唑噁唑骨架提供了另一种新颖的三唑基含有的6-硝基-2,3-二氢咪唑噁唑作为抗结核病的先导化合物。

  DOI：

  10.1039/c5ob00054h

文献信息

• [EN] 6-NITRO-2,3-DIHYDROIMIDAZO[2,1-b]OXAZOLES AND A PROCESS FOR THE PREPARATION THEREOF<br/>[FR] 6-NITRO-2,3-DIHYDROIMIDAZO[2,1-B]OXAZOLES ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2015049693A1

  公开（公告）日：2015-04-09

  The present invention relates to newer generation of triazoles, tetrazoles, isoxazoles, urea and sulphonamide functionalities containing 6-nitro-2, 3-dihydronitroimidazooxazoles agents of formula 1, their method of preparation, and their use as drugs for treating Mycobacterium tuberculosis,MDR-TB and XDR-TB either alone or in combination with other anti-tubercular agents. In the present invention, new generation 6-nitro-2, 3-dihydronitroimidazooxazoles agents also show acceptable pharmacokinetic properties and synergistic or additive effects with known anti-tubercular drugs.

  本发明涉及新一代三唑类、四唑类、异噁唑类、尿素和磺胺类功能团的含有6-硝基-2,3-二氢硝基咪唑噁唑类化合物的制备方法，以及它们作为治疗结核分枝杆菌、耐药结核分枝杆菌和极耐药结核分枝杆菌的药物的用途，可以单独使用，也可以与其他抗结核药物联合使用。在本发明中，新一代6-硝基-2,3-二氢硝基咪唑噁唑类化合物还表现出可接受的药代动力学性质，并与已知的抗结核药物呈现协同或加成效应。
• Sensor Array Composed of “Clicked” Individual Microcantilever Chips
  作者：François P. V. Paoloni、Sven Kelling、Juzheng Huang、Stephen R. Elliott

  DOI：10.1002/adfm.201000729

  日期：2011.1.21

  a small library of microcantilever (MC) chips presenting varied headgroups. A generic azide monolayer, bound to the MC surface, can be coupled with various alkynes using efficient "click" chemistry. This method is compatible with many functional groups, and novel headgroups are introduced on the MC surface by means of alkynes synthesized via a one‐step reaction. The surface "click" reaction reduces

  描述了一种简单的技术，可对呈现不同头基的微悬臂（MC）芯片小库进行功能化。可以使用有效的“喀哒”化学方法将键合到MC表面的通用叠氮化物单层与各种炔烃偶联。此方法与许多官能团兼容，并且通过一步反应合成的炔烃在MC表面引入了新的头基。表面“滴答”反应大大减少了合成和纯化相应的功能性硫醇所需的工作。该技术代表了我们小组开发的用于相移干涉显微镜（PSIM）读数的便捷补充工具。这些表面涂层对不同溶剂的亲和力可以通过测量悬臂梁的挠度来估计。由四个具有不同头基的单个MC芯片组成的概念验证传感器可以明确地区分神经气体模拟物的指纹响应与其他溶剂蒸气。
• Modular preparation of biphenyl triazoles via click chemistry as non-competitive hyaluronidase inhibitors
  作者：Yiman Qin、Guanyi Li、Ling Wang、Guangyuan Yin、Xiang Zhang、Hongxiang Wang、Pengfei Zheng、Wentao Hua、Yan Cheng、Yaxue Zhao、Jiong Zhang

  DOI：10.1016/j.bioorg.2024.107291

  日期：2024.5

  aging, sagging, and wrinkling, as well as inflammation and bacterial infections. In this study, to identify novel hyaluronidase inhibitors, we applied click chemistry for the modular synthesis of 370 triazoles in 96-well plates, starting with biphenyl azide. Utilizing an optimized turbidimetric screening assay in microplates, we identified Fmoc-containing triazoles and , as well as quinoline-containing

  透明质酸酶是药物发现中一个有前途的靶点，因为它在一系列生理和病理过程中过度表达，包括肿瘤迁移、皮肤老化、下垂和皱纹，以及炎症和细菌感染。在本研究中，为了鉴定新型透明质酸酶抑制剂，我们应用点击化学在 96 孔板中模块化合成 370 个三唑，从联苯叠氮化物开始。利用微孔板中优化的比浊筛选试验，我们鉴定出含 Fmoc 的三唑类和 ，以及含喹啉的三唑类和 ，作为高效的透明质酸酶抑制剂。随后的研究表明这些三唑可能与透明质酸酶的新结合位点相互作用。值得注意的是，这些抑制剂表现出最小的细胞毒性，并在 LPS 刺激的巨噬细胞中显示出有希望的抗炎作用。值得注意的是，浓度为 20 μM 的化合物可显着减少 74% 的 NO 释放。
• Design, synthesis and biological evaluation of LBM-A5 derivatives as potent P-glycoprotein-mediated multidrug resistance inhibitors
  作者：Yuxiang Wu、Miaobo Pan、Yuxuan Dai、Baomin Liu、Jian Cui、Wei Shi、Qianqian Qiu、Wenlong Huang、Hai Qian

  DOI：10.1016/j.bmc.2016.03.065

  日期：2016.5

  A novel series of P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) inhibitors with triazol-N-phenethyl-tetrahydroisoquinoline or triazol-N-ethyl-tetrahydroisoquinoline scaffold were designed and synthesized via click chemistry. Most of the synthesized compounds showed higher reversal activity than verapamil (VRP). Among them, the most potent compound 4 showed a comparable activity with the known potent P-gp inhibitor WK-X-34 with lower cytotoxicity toward K562 cells (IC50 > 100 mu M). Compared with VRP, compound 4 exhibited more potency in increasing drug accumulation in K562/A02 MDR cells. Moreover, compound 4 could significantly reverse MDR in a dose-dependent manner and also persist longer chemo-sensitizing effect than VRP with reversibility. Further mechanism studies revealed that compound 4 could remarkably increase the intracellular accumulation of Adriamycin (ADM) in K562/A02 cells as well as inhibit rhodamine-123 (Rh123) efflux from the cells. These results suggested that compound 4 may represent a promising candidate for developing P-gp-mediated MDR inhibitors. (C) 2016 Elsevier Ltd. All rights reserved.
• [EN] PROCESS FOR THE PREPARATION OF DERIVATIVES OF 1,1-DIALKYLETHANE-1,2-DIOLS AS USEFUL INTERMEDIATES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE 1,1-DIALKYLÉTHANE-1,2-DIOLS EN TANT QU'INTERMÉDIAIRES UTILES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2020202205A1

  公开（公告）日：2020-10-08

  The invention provides a novel and practical route of synthesis the substituted diol intermediates, 1,1-dialkylethane-1,2-diols, useful for the preparation of various 6-nitro-2,3-dihydroimidazo[2,1-b]oxazole containing drugs. Specifically, the invention provides a novel and practical route of an intermediate which is used for the synthesis of Delamanid.