4-fluoro-N-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide | 1206850-07-8

• 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: 4-fluoro-N-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
• 英文别名: 4-fluoro-N-methyl-N-(prop-2-inyl)benzenesulfonamide；4-fluoro-N-methyl-N-(prop-2-ynyl)benzenesulfonamide；4-fluoro-N-methyl-N-prop-2-ynylbenzenesulfonamide
• CAS: 1206850-07-8
• 化学式: C₁₀H₁₀FNO₂S
• 分子量: 227.259
• InChiKey: MXGGJMKZVICAJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-fluoro-N-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 、 N-(5-azidopentanoyl)-L-methionyl-L-glutaminyl-L-seryl-O-phosphono-L-threonyl-L-prolyl-L-leucine 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 以36%的产率得到
  参考文献：
  名称：

  4- [18 F]氟-N-甲基-N-（丙基-2-yn-1-基）苯磺酰胺（[18 F] F-SA）：通用的构建基，用于用氟标记肽，蛋白质和寡核苷酸-18通过Cu（I）介导的点击化学

  摘要：

  叠氮化物与炔烃之间的Cu（I）介导的[3 + 2]环加成反应已发展成为放射性药物化学中一种有价值的生物共轭工具。我们开发了一种简单，方便，可靠的4- [ 18 F]氟-N-甲基-N-（丙基-2-yn-1-基）苯磺酰胺（[ 18 F] F-SA）放射合成方法基于磺酰胺的点击化学构件。[ 18 F] F-SA可以在遥控合成装置中以32±5％的衰变校正放射化学收率制备，总合成时间为80分钟。确定的[ 18 F] F-SA亲脂性（log P = 1.7）允许在水溶液中处理放射性示踪剂。通过标记模型肽（磷酸肽），蛋白质（HSA）和寡核苷酸（L-RNA），证明了[ 18 F] F-SA作为点击化学构件的多功能性。获得的放射化学产率分别为77％（磷酸肽），55-60％（HSA）和25％（L-RNA）。尽管最近出现了许多用于生物聚合物18 F标记的高度创新的新型生物缀合方法，但使用[ 18 F] F-SA

  DOI：

  10.1007/s00726-012-1450-4
• 作为产物：
  描述：

  N-甲基炔丙基胺 、 4-氟苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以99%的产率得到4-fluoro-N-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  4- [18 F]氟-N-甲基-N-（丙基-2-yn-1-基）苯磺酰胺（[18 F] F-SA）：通用的构建基，用于用氟标记肽，蛋白质和寡核苷酸-18通过Cu（I）介导的点击化学

  摘要：

  叠氮化物与炔烃之间的Cu（I）介导的[3 + 2]环加成反应已发展成为放射性药物化学中一种有价值的生物共轭工具。我们开发了一种简单，方便，可靠的4- [ 18 F]氟-N-甲基-N-（丙基-2-yn-1-基）苯磺酰胺（[ 18 F] F-SA）放射合成方法基于磺酰胺的点击化学构件。[ 18 F] F-SA可以在遥控合成装置中以32±5％的衰变校正放射化学收率制备，总合成时间为80分钟。确定的[ 18 F] F-SA亲脂性（log P = 1.7）允许在水溶液中处理放射性示踪剂。通过标记模型肽（磷酸肽），蛋白质（HSA）和寡核苷酸（L-RNA），证明了[ 18 F] F-SA作为点击化学构件的多功能性。获得的放射化学产率分别为77％（磷酸肽），55-60％（HSA）和25％（L-RNA）。尽管最近出现了许多用于生物聚合物18 F标记的高度创新的新型生物缀合方法，但使用[ 18 F] F-SA

  DOI：

  10.1007/s00726-012-1450-4

文献信息

• Radiolabelling of proteins with fluorine-18 via click chemistry
  作者：Theres Ramenda、Torsten Kniess、Ralf Bergmann、Jörg Steinbach、Frank Wuest

  DOI：10.1039/b916075b

  日期：——

  The study describes for the first time the application of Cu(I)-mediated 1,3-dipolar [3+2]cycloaddition for the labelling of proteins with the short-lived positron emitter fluorine-18 as exemplified with azide-functionalized human serum albumin (HSA).

  该研究首次介绍了以叠氮功能化人血清白蛋白（HSA）为例，应用 Cu(I)-mediated 1,3-dipolar [3+2]cycloaddition 技术用短寿命正电子发射体氟-18 标记蛋白质。
• Development and Evaluation of Endothelin-A Receptor (Radio)Ligands for Positron Emission Tomography
  作者：Kristin Michel、Katrin Büther、Marilyn P. Law、Stefan Wagner、Otmar Schober、Sven Hermann、Michael Schäfers、Burkhard Riemann、Carsten Höltke、Klaus Kopka

  DOI：10.1021/jm101110w

  日期：2011.2.24

  tumor metastasis. A previously reported promising radioligand for positron emission tomography (PET) based on the non-peptide ETA receptor antagonist PD 156707 showed specific binding to target receptors in the myocardium but high accumulation in bile and intestine, probably because of its high lipophilicity. In this study we describe the synthesis of a series of fluorinated derivatives with hydrophilic

  内皮素（ET）受体的表达和功能在心血管疾病，肿瘤进展和肿瘤转移中异常。先前报道的基于非肽ET A受体拮抗剂PD 156707的用于正电子发射断层扫描（PET）的有前途的放射性配体显示出与心肌中靶标受体的特异性结合，但在胆汁和肠中高积累，这可能是由于其高亲脂性。在这项研究中，我们描述了一系列具有亲水结构单元的氟化衍生物的合成。所有化合物被评估为高亲和力ET甲受体配体（16，17，23 - 26，ķ我= 1.4−7.9 nM），并且具有比ET B受体更高的亚型选择性。[ 18 F] 3-苯并[1,3]二氧杂环戊烯-5-基-4- 3- [1-（2- 2- [2-（2-氟乙氧基）乙氧基]乙氧基}乙基）-1- ħ -合成了[1,2,3]三唑-4-基甲氧基] -4,5-二甲氧基苄基} -5-羟基-5-（4-甲氧基苯基）-5 H-呋喃-2-酮（[ 18 F] 17）作为该系列的放射性配体之一，在人血
• 18F—tagged inhibitors of prostate specific membrane antigen (PSMA) and their use as imaging agents for prostate cancer
  申请人：DEUTSCHES KREBSFORSCHUNGSZENTRUM

  公开号：US10815200B2

  公开（公告）日：2020-10-27

  The present invention generally relates to the field of radiopharmaceuticals and their use in nuclear medicine as tracers and imaging agents for various disease states of prostate cancer.

  本发明一般涉及放射性药物领域及其在核医学中作为前列腺癌各种疾病状态的示踪剂和成像剂的用途。
• Inverse 1,2,3-Triazole-1-yl-ethyl Substituted Hydroxamates as Highly Potent Matrix Metalloproteinase Inhibitors: (Radio)synthesis, in Vitro and First in Vivo Evaluation
  作者：Verena Hugenberg、Burkhard Riemann、Sven Hermann、Otmar Schober、Michael Schäfers、Katrin Szardenings、Artem Lebedev、Umesh Gangadharmath、Hartmuth Kolb、Joseph Walsh、Wei Zhang、Klaus Kopka、Stefan Wagner

  DOI：10.1021/jm4006753

  日期：2013.9.12

  Noninvasive imaging and quantification of matrix metalloproteinase (MMP) activity in vivo are of great (pre)clinical interest. This can potentially be realized by using radiolabeled MMP inhibitors (MMPIs) as positron emission tomography (PET) imaging agents. Triazole-substituted MMPIs, discovered by our group, are highly potent inhibitors of MMP-2, -8, -9, and -13. The triazole ring and its position contribute significantly to the potency of the MMP inhibitor. To evaluate structure activity relationships (SARs) of the initially discovered triazole-substituted MMPIs, an additional CH2-group between the backbone of the molecule and the triazole core was inserted, and the triazole ring was "inversed" by switching the alkyne and azide groups. Similar to the original triazole-substituted hydroxamates, the inverse triazole MMPIs are excellent inhibitors with promising in vivo properties. Pharmacokinetic properties and metabolic stability of an F-18-labeled candidate in mice were investigated.
• A New Generation of Radiofluorinated Pyrimidine-2,4,6-triones as MMP-Targeted Radiotracers for Positron Emission Tomography
  作者：Daniela Schrigten、Hans-Jörg Breyholz、Stefan Wagner、Sven Hermann、Otmar Schober、Michael Schäfers、Günter Haufe、Klaus Kopka

  DOI：10.1021/jm201142w

  日期：2012.1.12

  Radiolabeled C-5-disubstituted pyrimidine-2,4,6-triones have recently been suggested by our group as a class of potent matrix metalloproteinase (MMP) targeted radiotracers that can noninvasively visualize activated MMPs by means of positron emission tomography (PET). MMPs belong to the zinc- and calcium-dependent endopeptidases which are involved in the proteolytic degradation of components of the extracellular matrix (ECM) but also are capable of processing and releasing bioactive molecules such as growth factors, proteinase inhibitors, and cytokines. Locally increased levels of activated MMPs modulate and contribute to the progression of various diseases, such as cancer, atherosclerosis, stroke, arthritis, and others. Therefore, activated MMPs are suitable biological targets for the specific and noninvasive visualization of aforementioned pathologies in vivo. On the basis of our recent results, we here describe a series of new fluorinated pyrimidine-2,4,6-triones of the second generation with maintained MAP inhibition potencies (IC50 = 4-605 nM), which are fine-tuned toward more hydrophilic versions, and show the improved biodistribution behavior of one selected radiofluorinated pyrimidine-2,4,6-trione by means of small-animal PET.