2-fluoroethyl-4-nitrobenzene sulfonate | 141516-54-3

• 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: 2-fluoroethyl-4-nitrobenzene sulfonate
• 英文别名: 2-fluoroethyl 4-nitrobenzenesulfonate；Benzenesulfonic acid, 4-nitro-, 2-fluoroethyl ester
• CAS: 141516-54-3
• 化学式: C₈H₈FNO₅S
• 分子量: 249.22
• InChiKey: NZRPWDQOJQBQCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-fluoroethyl-4-nitrobenzene sulfonate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Amide and Sulfonate Groups Based on the Sulfonylurea Receptor Protein Binding Site for Diflubenzuron and Glibenclamide

  摘要：

  On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by H-1 nuclear magnetic resonance (NMR) and elemental analysis [or high-resolution mass spectrometry (HRMS)]. The larvicidal activities of the new compounds against oriental armyworm and diamondback moth were evaluated. Compound II-3 showed nearly the same level of insecticidal activity against oriental armyworm as commercial insecticide flucycloxuron and, thus, emerged as a new lead compound for the development of new benzoylurea insecticides.

  DOI：

  10.1021/jf304468b
• 作为产物：
  描述：

  2-氟乙醇 、 对硝基苯磺酰氯 在 potassium trimethylsilonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以59%的产率得到2-fluoroethyl-4-nitrobenzene sulfonate
  参考文献：
  名称：

  氟-18拉贝的氮杂肽腈的合成和放射药理学表征，可作为半胱氨酸组织蛋白酶在体内成像的潜在PET示踪剂

  摘要：

  由于其对肿瘤相关的组织蛋白酶L，S，K和B具有高度亲和力，因此制备了一种基于氮杂肽腈化学型的氟化组织蛋白酶抑制剂，并选择用于正电子发射断层显像（PET）示踪剂开发。通过使用2- [ 18 F]氟代乙基羟乙基磺酸盐作为修复剂，可进行高效，可靠的两步，一锅式放射合成。通过放射性代谢物分析和小动物正电子发射断层显像，在正常大鼠体内，离体和体内研究了所得放射性示踪化合物的药代动力学特性。这些研究表明示踪剂与血液中的谷胱甘肽快速共轭形成，这与血液清除缓慢有关。发达18的潜力通过动态小动物PET成像在带有人NCI-H292肺癌细胞系肿瘤的裸鼠中研究了与肿瘤相关的组织蛋白酶活性相关的F标记探针。对获得的图像数据的计算分析表明放射性示踪剂在肿瘤中的时间依赖性积累。通过用特异性抗体的免疫组织化学证实了靶标酶在肿瘤中的表达。这表明，尽管氮杂双肽腈具有不利的药代动力学，但它们仍可能在体内靶向硫醇依赖性组织蛋白酶。

  DOI：

  10.1002/cmdc.201300135

文献信息

• Radiosyntheses and reactivities of novel [18F]2-fluoroethyl arylsulfonates
  作者：John L. Musachio、Jay Shah、Victor W. Pike

  DOI：10.1002/jlcr.991

  日期：2005.9

  [18F]2-Fluoroethyl tosylate ([18F]FEOX, X=Ts) is widely used for labeling radiotracers for positron emission tomography (PET). Little work has been reported on syntheses of other [18F]2-fluoroethyl arylsulfonates ([18F]FEOX) that bear a less electron-rich aryl group, even though these might offer enhanced reactivities. Thus, a series of novel [18F]FEOX (X=benzenesulfonyl, brosyl, nosyl, 3,4-dibromobenzenesulfonyl) were synthesized and reactivities compared to [18F]FEOTs. Precursors for radiolabeling (bis-ethylene glycol arylsulfonates) and reference FEOX were synthesized (alcohol+arylsulfonyl chloride+KOSiMe3 in THF). Regardless of substitution pattern, [18F]FEOX (110°C, 5 min, acetonitrile) were obtained in similar decay-corrected isolated radiochemical yields (RCY; 47–53%). All [18F]FEOX gave excellent RCYs (64–87%) of the dopamine uptake radioligand, [18F]FECNT (130°C, 10 min, acetonitrile). The 3,4-dibromobenzensulfonate gave the highest RCY of [18F]FECNT (87%) and this HPLC-purified labeling agent was used directly for efficient [18F]FECNT production. When the secondary aniline of an amyloid probe (HM-IMPY) or p-nitrophenol was reacted with [18F]FEOX, RCYs were appreciably higher for brosylate and nosylate than for tosylate, while 3,4-dibromobenzenesulfonate again gave the highest RCY. Owing to the high reactivity of the new [18F]FEOX and their ease of syntheses via stable precursors, such agents (particularly 3,4-dibromobenzenesulfonate) should be considered as alternatives to [18F]FEOTs. Copyright © 2005 John Wiley & Sons, Ltd.

  [18F]2-氟乙基对甲苯磺酸酯([18F]FEOX, X=Ts)广泛用于正电子发射断层扫描(PET)示踪剂的标记。尽管可能具有增强的反应性,但关于合成其他[18F]2-氟乙基芳磺酸酯([18F]FEOX)的研究报道很少,特别是含有较少电富集芳基的化合物。因此,合成了一系列新型[18F]FEOX(X=苯磺酰基、对溴苯磺酰基、对硝基苯磺酰基、3,4-二溴苯磺酰基)并比较了其与[18F]FEOTs的反应活性。放射性标记前体(双乙二醇芳磺酸酯)和参考FEOX通过以下方法合成:乙醇+芳磺酰氯+KOSiMe3(在四氢呋喃中)。无论取代模式如何,[18F]FEOX(110°C, 5 min, 乙腈)均以相似的衰减校正的放射化学产率(RCY; 47–53%)获得。所有[18F]FEOX均提供了优异的多巴胺摄取放射配体[18F]FECNT的RCY(64–87%)(130°C, 10 min, 乙腈)。3,4-二溴苯磺酸酯提供了最高的[18F]FECNT的RCY(87%),该高效液相色谱纯化的标记试剂直接用于高效生产[18F]FECNT。当与淀粉样蛋白探针(HM-IMPY)的二级苯胺或对硝基苯酚反应时,[18F]FEOX的RCY明显高于对溴苯磺酸酯和对硝基苯磺酸酯,而3,4-二溴苯磺酸酯再次提供了最高的RCY。由于新型[18F]FEOX的高反应性和通过稳定前体合成的简便性,这些试剂(特别是3,4-二溴苯磺酸酯)应被视为[18F]FEOTs的替代品。版权所有 © 2005 John Wiley & Sons, Ltd.
• A New Precursor for the Radiosynthesis of 6-O-(2-[¹⁸F]Fluoroethyl)-6-Odesmethyl- diprenorphine ([¹⁸F]FE-DPN) by Nucleophilic Radiofluorination
  作者：János Marton、Paul Cumming、Beate Bauer、Gjermund Henriksen

  DOI：10.2174/1570178617999200719153812

  日期：2021.5

  We present the preparation of the new precursor 6-O-(2-tosyloxyethoxy)-6-O-desmethyl-3- O-trityl-diprenorphine (TE-TDDPN) for a one-pot, two-step nucleophilic radiosynthesis of 6-O-(2- [18F]fluoroethyl-6-O-desmethyl-diprenorphine ([18F]FE-DPN). The route to the precursor consists of a five-step synthesis starting from diprenorphine. We also provide alternative synthesis routes for the cold reference standard and the complete 1H- and 13C-NMR assignment of the prepared derivatives.

  我们提出了新前体6-O-(2-对甲苯磺酰氧乙氧基)-6-O-去甲基-3-O-三苯甲基-二氢可待因（TE-TDDPN）的制备方法，用于一锅法、两步核磁合成制备6-O-(2-[18F]氟乙基-6-O-去甲基-二氢可待因 ([18F]FE-DPN)。前体的合成路线包括从二氢可待因开始的五步合成。我们还提供了用于冷参考标准的替代合成路线，并对制备的衍生物进行了完整的1H和13C-NMR分配。
• [EN] RADIOLABELED ERLOTINIB ANALOGS AND USES THEREOF<br/>[FR] ANALOGUES RADIOMARQUÉS DE L'ERLOTINIB ET LEURS UTILISATIONS
  申请人：HADASIT MED RES SERVICE

  公开号：WO2017122205A1

  公开（公告）日：2017-07-20

  Radiolabeled compounds which are erlotinib analogs that feature a radioactive halogen and processes of preparing same are disclosed. Uses of these radiolabeled compounds in radioimaging, for identifying and monitoring a level, distribution and/or mutational status of deregulated EGFR, and/or in radiotherapy, are also disclosed.

  本发明公开了具有放射性卤素的厄洛替尼类似物的放射性标记化合物及其制备方法。本发明还公开了这些放射性标记化合物在放射性成像中的用途，用于识别和监测EGFR失调的水平、分布和/或突变状态，以及在放射治疗中的用途。
• Radiolabeled erlotinib analogs and uses thereof
  申请人：Hadasit Medical Research Services and Development Ltd.

  公开号：US10710968B2

  公开（公告）日：2020-07-14

  Radiolabeled compounds which are erlotinib analogs that feature a radioactive halogen and processes of preparing same are disclosed. Uses of these radiolabeled compounds in radioimaging, for identifying and monitoring a level, distribution and/or mutational status of deregulated EGFR, and/or in radiotherapy, are also disclosed.

  公开了具有放射性卤素的厄洛替尼类似物放射性标记化合物及其制备方法。还公开了这些放射性标记化合物在放射成像中的用途，用于识别和监测失调表皮生长因子受体的水平、分布和/或突变状态，和/或用于放射治疗。
• Diaryl-Substituted (Dihydro)pyrrolo[3,2,1-<i>hi</i>]indoles, a Class of Potent COX-2 Inhibitors with Tricyclic Core Structure
  作者：Markus Laube、Cemena Gassner、Sai Kiran Sharma、Robert Günther、Arne Pigorsch、Jonas König、Martin Köckerling、Frank Wuest、Jens Pietzsch、Torsten Kniess

  DOI：10.1021/acs.joc.5b00537

  日期：2015.6.5

  A new compound class of diaryl-substituted heterocycles with tricyclic dihydropyrrolo[3,2,1-hi]indole and pyrrolo[3,2,1-hi]indole core structures has been designed and was synthesized by a modular sequence of Friedel-Crafts acylation, amide formation, and McMurry cyclization. This synthesis route represents a novel and versatile access toward dihydropyrrolo[3,2,1-hi]indoles and is characterized by good chemical yields and high modularity. From a set of 19 derivatives, 11 candidates were selected for determination of their COX inhibition potency and were found to be selective inhibitors with high affinity to COX-2 (IC50 ranging from 20-2500 nM and negligible inhibition of COX-1). The binding mode of the novel inhibitors in the active side of COX-2 was calculated in silico using the protein ligand docking program GOLD by application of the molecular structures of two compounds derived from X-ray crystallography. Two novel compounds with high affinity to COX-2 (6k = 70 nM, 8e = 60 nM) have a fluoro substituent, making them promising candidates for the development of F-18-radiolabeled COX-2 inhibitors for imaging purposes with positron emission tomography (PET).