4-(4-Fluoro-phenyl)-[1,2,4]triazole-3,5-dione | 886496-59-9

• 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-(4-Fluoro-phenyl)-[1,2,4]triazole-3,5-dione
• 英文别名: 4-(4-fluorophenyl)-1,2,4-triazole-3,5-dione
• CAS: 886496-59-9
• 化学式: C₈H₄FN₃O₂
• mdl: MFCD04117471
• 分子量: 193.137
• InChiKey: MDTAFFPODYINGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Fluoro-phenyl)-[1,2,4]triazole-3,5-dione 、 3,28-diacetoxy-18,19-epoxylupane 在 乙酸酐 、 对甲苯磺酸 作用下， 以 甲苯 、 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 [(1S,3R,4R,7S,9R,12R,13S,16R,19S)-7-acetyloxy-22-(4-fluorophenyl)-4,8,8,12,13-pentamethyl-21,23-dioxo-19-propan-2-yl-20,22,24-triazaheptacyclo[14.8.2.03,12.04,9.013,25.019,26.020,24]hexacos-25-en-16-yl]methyl acetate
  参考文献：
  名称：

  杂环甜菜碱衍生物的合成及抗利什曼活性

  摘要：

  桦木素，一种天然存在的丰富的三萜，可通过四个步骤转化为3,28-二-O-乙酰基acetyl- 12,18-二烯。在3,28-二-O-乙酰基lu- 12,18-二烯的存在下，用碘代苯二乙酸酯将各种4-取代的脲唑氧化为相应的脲嗪时，会生成新的杂环桦木衍生物。在微孔板分析中以50μM的浓度检测了这些betulin衍生物对抑制致死性内脏利什曼病的物种Leishmania donovani axenic amastigotes的生长的能力。胃肠道50测定最有效化合物的浓度（50％生长抑制的浓度），并评估其对人巨噬细胞THP-1的细胞毒性。还检查了对在巨噬细胞中生长的杜氏乳酸杆菌的抗利什曼活性。3,28-二-O-乙酰基lupa- 12,18-二烯和4-甲基尿嘧啶之间的杂环加合物是最有效的衍生物，其 对杜氏乳酸链球菌的GI 50 = 8.9μM。

  DOI：

  10.1016/j.bmc.2010.01.003
• 作为产物：
  描述：

  ethyl 2-(p-fluorophenylcarbamoyl)hydrazine-1-carboxylate 在 calcium hypochlorite 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 4-(4-Fluoro-phenyl)-[1,2,4]triazole-3,5-dione
  参考文献：
  名称：

  乌拉唑的望远镜氧化和环加成获得二氮杂环丁烯

  摘要：

  我们以前访问二氮杂环丁烯支架的方法不允许修改源自 1,2,4-三唑啉-3,5-二酮成分的取代基。我们已经规避了这一挑战，并扩大了对脚手架额外结构多样性的访问。伸缩的乌拉唑氧化和路易斯酸催化的环化提供了 R 3取代的二氮杂环丁烯。次氯酸钙介导的乌拉唑氧化，随后 MgCl 2催化所得三唑啉二酮与硫代炔烃的环化促进了二氮杂环丁烯的形成，该二氮杂环丁烯在源自三唑啉二酮组分的R 3位置带有取代。

  DOI：

  10.1021/acs.joc.2c00280

文献信息

• Chiral Phosphoric Acid-Catalyzed Remote Control of Axial Chirality at Boron–Carbon Bond
  作者：Junxian Yang、Ji-Wei Zhang、Wen Bao、Sheng-Qi Qiu、Shaoyu Li、Shao-Hua Xiang、Jun Song、Junmin Zhang、Bin Tan

  DOI：10.1021/jacs.1c05079

  日期：2021.8.25

  desymmetrization strategy reported herein. The electrophilic aromatic substitution reaction of 3,5-disubsituted phenols with diazodicarboxamides could afford these axially chiral structures in good efficiency with excellent enantiocontrol. The efficient long-range stereochemical control is achieved by multiple well-defined H-bonding interactions between chiral phosphoric acid and both substrates. Meanwhile, the

  通过本文报道的手性磷酸催化去对称化策略，实现了先前难以捉摸的具有 C-B 立体轴的轴向手性 B-芳基-1,2-氮杂硼烷的催化对映选择性构建。3,5-二取代苯酚与重氮二甲酰胺的亲电芳香取代反应可以有效地提供这些轴向手性结构，并具有优异的对映控制。有效的远程立体化学控制是通过手性磷酸和两种底物之间的多个明确定义的 H 键相互作用实现的。同时，1,2-氮杂硼碱中弱酸性的N-H作为H键供体可以显着缩短反应时间。反应的可扩展性和产物中 N-N 键的易裂解进一步证明了该方法的实用性。
• Novel Strategy for Non-Aqueous Bioconjugation of Substituted Phenyl-1,2,4-triazole-3,5-dione Analogues
  作者：Hugh G. Hiscocks、Alison T. Ung、Giancarlo Pascali

  DOI：10.3390/molecules27196667

  日期：——

  A novel 4-[4-(pentafluoro-λ⁶-sulfanyl)phenyl]-1,2,4-triazole-3,5-dione (5a) was synthesised as a potential [18F]radio-prosthetic group for radiolabelling peptides and proteins via selective bioconjugation with the phenolic side chains of tyrosine residues. Preliminary conjugation tests revealed the rapid hydrolysis of 5a under semi-aqueous conditions; these results led to further investigation into the electronic substituent effects of PTAD derivatives and corresponding hydrolytic stabilities. Five derivatives of 5a with para substituents of varying electron donating and withdrawing effects were synthesised for the investigation. The bioconjugation of these derivatives with model tyrosine was monitored in both aqueous and organic media in the presence of a variety of catalysts. From these investigations, we have found HFIP to be an effective catalyst when used in tandem with DCM as a solvent to give PTAD-tyrosine conjugate products (6a–f) in satisfactory to good yields (54–79%), whereas analogous reactions performed in acetonitrile were unsuccessful. The discovery of this system has allowed for the successful conjugation of electron-deficient PTAD derivatives to tyrosine, which would otherwise be unachievable under aqueous reaction conditions. The inclusion of these electron-deficient, fluorinated PTAD derivatives for use in the PTAD-tyrosine conjugation will hopefully broaden their applicability within fields such as 19F-MRI and PET imaging.

  一种新型的4-[4-(全氟-λ⁶-硫醇基)苯基]-1,2,4-三唑-3,5-二酮（5a）被合成为一种潜在的[18F]放射性假体基团，通过与酪氨酸残基的酚侧链选择性生物共轭，用于标记肽和蛋白质。初步的共轭试验揭示了在半水条件下5a的快速水解，这些结果导致进一步研究PTAD衍生物的电子取代效应和相应的水解稳定性。合成了五种带有不同电子给予和提取效应的对位取代基的5a衍生物进行研究。这些衍生物与模型酪氨酸在水和有机介质中在各种催化剂的存在下进行生物共轭反应的监测。从这些研究中，我们发现在DCM作为溶剂的情况下，HFIP作为有效的催化剂可以使PTAD-酪氨酸共轭产物（6a-f）以令人满意到良好的收率（54-79％）得到形成，而在乙腈中进行的类似反应则失败了。这个体系的发现使得电子不足的PTAD衍生物成功地与酪氨酸共轭，否则在水反应条件下将无法实现。这些电子不足的、氟化的PTAD衍生物的加入，将有望扩大它们在19F-MRI和PET成像等领域的应用。
• Discovery of Novel Benzopyranyl Tetracycles that Act as Inhibitors of Osteoclastogenesis Induced by Receptor Activator of NF-κB Ligand
  作者：Mingyan Zhu、Myung Hee Kim、Sanghee Lee、Su Jung Bae、Seong Hwan Kim、Seung Bum Park

  DOI：10.1021/jm1011269

  日期：2010.12.23

  A novel benzopyran-fused molecular framework 7ai was discovered as a specific inhibitor of RANKL-induced osteoclastogenesis using a cell-based TRAP activity assay from drug-like small-molecule libraries constructed by diversity-oriented synthesis. Its inhibitory activity was confirmed by in vitro evaluations including specific inhibition of RANKL-induced ERK phosphorylation and NF-kappa B transcriptional activation. 7ai can serve as a specific small-molecule modulator for mechanistic studies of RANKL-induced osteoclast differentiation as well as a potential lead for the development of antiresorptive drugs.
• Development of Biocompatible Ene-Ligation Enabled by Prenyl-Based β-Caryophyllene with Triazoline/Selectfluor under Physiological Conditions
  作者：Sheng Wang、Yuanyuan Li、Hongling Zhou、Li Wang、Rui Wang

  DOI：10.1021/acs.joc.2c00841

  日期：2022.7.1
• Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives
  作者：Sami Alakurtti、Tuomo Heiska、Alexandros Kiriazis、Nina Sacerdoti-Sierra、Charles L. Jaffe、Jari Yli-Kauhaluoma

  DOI：10.1016/j.bmc.2010.01.003

  日期：2010.2

  Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives were examined in a microplate assay at 50 μM for

  桦木素，一种天然存在的丰富的三萜，可通过四个步骤转化为3,28-二-O-乙酰基acetyl- 12,18-二烯。在3,28-二-O-乙酰基lu- 12,18-二烯的存在下，用碘代苯二乙酸酯将各种4-取代的脲唑氧化为相应的脲嗪时，会生成新的杂环桦木衍生物。在微孔板分析中以50μM的浓度检测了这些betulin衍生物对抑制致死性内脏利什曼病的物种Leishmania donovani axenic amastigotes的生长的能力。胃肠道50测定最有效化合物的浓度（50％生长抑制的浓度），并评估其对人巨噬细胞THP-1的细胞毒性。还检查了对在巨噬细胞中生长的杜氏乳酸杆菌的抗利什曼活性。3,28-二-O-乙酰基lupa- 12,18-二烯和4-甲基尿嘧啶之间的杂环加合物是最有效的衍生物，其 对杜氏乳酸链球菌的GI 50 = 8.9μM。