2-[(4-氟苯基)氨基]-2-氧代-乙酸乙酯 | 69065-91-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-[(4-氟苯基)氨基]-2-氧代-乙酸乙酯
• 中文别名: 2-(4-氟苯胺基)-2-氧代乙酸乙酯
• 英文名称: ethyl 4'-fluorooxanilate
• 英文别名: ethyl 2-((4-fluorophenyl)amino)-2-oxoacetate；Ethyl 2-(4-fluoroanilino)-2-oxoacetate
• CAS: 69065-91-4
• 化学式: C₁₀H₁₀FNO₃
• mdl: MFCD00119045
• 分子量: 211.193
• InChiKey: OUBZLXSQKQMFAH-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122°C
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2924299090
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P260,P264,P273,P301+P312,P305+P351+P338,P314
• 危险品运输编号：
  3077
• 危险性描述：
  H302,H319,H372,H410
• 储存条件：
  室温、密封、干燥保存。

反应信息

• 作为反应物：
  描述：

  2-[(4-氟苯基)氨基]-2-氧代-乙酸乙酯 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 [(4-氟苯基)氨基](氧代)乙酸
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Activity of Entry Inhibitors That Target the CD4-Binding Site of HIV-1

  摘要：

  The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next-generation therapeutics and microbicides against HIV-1.

  DOI：

  10.1021/jm3002247
• 作为产物：
  描述：

  2-[(4-氟苯基)氨基]乙酸乙酯 在 chlorophyll 作用下， 以 乙腈 为溶剂， 以87 %的产率得到2-[(4-氟苯基)氨基]-2-氧代-乙酸乙酯
  参考文献：
  名称：

  Visible light promoted and chlorophyll catalyzed α-oxidation of amines to amides under aerobic conditions: Synthesis of 3,4-dihydroisoquinolin-1(2H)-ones and N-phenyl oxalamides

  摘要：

  DOI：

  10.1016/j.tetlet.2023.154579

文献信息

• <i>N</i>-Acylanilines, Herbicide−CHA Chimera, and Amino Acid Analogues as Novel Chemical Hybridizing Agents for Wheat (<i>Triticum aestivum</i> L.)
  作者：Kajal Chakraborty、C. Devakumar

  DOI：10.1021/jf051458t

  日期：2005.10.1

  development, chemical induction of male sterility mediated technology based on chemical hybridizing agents (CHAs) holds a great potential. N-Acylaniline derivatives, namely, ethyl 4'-fluoro oxanilate (1) and ethyl 4'-trifluoromethyl oxanilate (2) containing halogen atoms in the para position of the aryl ring and substituted amide linkage (-CO-NH-) in the acyl side chain induced >98% spikelet sterility on three

  在没有可行的杂交小麦开发替代技术的情况下，基于化学杂交剂（CHA）的雄性不育介导技术的化学诱导具有巨大的潜力。N-酰基苯胺衍生物，即在芳基环对位含有卤素原子并在其芳基中的取代酰胺键（-CO-NH-）的4'-氟代草酸乙酯（1）和4'-三氟代甲基草酸乙酯（2）。酰基侧链在1500 ppm时对三种基因型小麦，即PBW 343，HD 2046和HD 2733诱导的小穗不育性> 98％。以甘氨酸和丙氨酸为模板，将活性部分以除草剂-CHA嵌合体和氨基酸类似物的形式掺入。通过合成除草剂的嵌合结构，可以使目标活性更具选择性（2，4-二氯苯氧基乙酸和dalapon）和最活跃的CHA模板，即4-氟苯胺基和β-乙氧羰基部分。在除草剂-CHA嵌合体中，2'，4'-草酸二氯苯基乙酯（14）诱导了79.11％的雄性不育，而2-氧代-3-氮杂氮杂双苄基甲基酯（20）最佳，在HD 2733中诱导了73.87％的雄性不育。
• Design, synthesis and evaluation of antiproliferative and antitubulin activities of 5-methyl-4-aryl-3-(4-arylpiperazine-1-carbonyl)-4H-1,2,4-triazoles
  作者：Chao Wang、Yuelin Li、Tong Liu、Zeyu Wang、Yujing Zhang、Kai Bao、Yingliang Wu、Qi Guan、Daiying Zuo、Weige Zhang

  DOI：10.1016/j.bioorg.2020.103909

  日期：2020.11

  Moreover, the tubulin polymerization experiments indicated that compound 6e could inhibit the tubulin polymerization. Immunofluorescence study and cell cycle analysis clearly revealed compound 6e could disrupt intracellular microtubule organization, arrest cell cycle at the G2/M phase. In addition, molecular docking analysis demonstrated the interaction of compound 6e at the colchicine-binding site of tubulin

  设计了一系列以1,2,4-三唑为氢键受体的新型5-甲基-4-芳基-3-（4-芳基哌嗪-1-羰基）-4 H -1,2,4-三唑合成并评估了它们的抗增殖和微管蛋白聚合抑制活性。它们中的一些在体外对三种癌细胞系（包括SGC-7901，A549和HeLa）表现出中等活性。化合物6e对三种癌细胞表现出最高的效力。此外，微管蛋白聚合实验表明化合物6e可以抑制微管蛋白聚合。免疫荧光研究和细胞周期分析清楚地表明了化合物6e可能破坏细胞内微管组织，使细胞周期停滞在G2 / M期。另外，分子对接分析表明化合物6e在微管蛋白的秋水仙碱结合位点相互作用。这些初步结果表明，化合物6e是一种新型秋水仙碱结合位点抑制剂，值得进一步研究。
• Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase
  作者：Sarah E. Winterton、Emanuela Capota、Xiaoyu Wang、Hong Chen、Prema L. Mallipeddi、Noelle S. Williams、Bruce A. Posner、Deepak Nijhawan、Joseph M. Ready

  DOI：10.1021/acs.jmedchem.8b00052

  日期：2018.6.28

  Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development

  硬脂酰辅酶A去饱和酶（SCD）催化饱和脂肪酸向不饱和脂肪酸转化的第一步。膜完整性和细胞增殖需要不饱和脂肪酸。由于这些原因，SCD抑制剂代表了潜在的癌症治疗方法。但是，具有内在活性的SCD抑制剂会导致皮肤毒性，这对它们的发展构成了障碍。我们最近描述了一系列草酸二酰胺，它们通过CYP4F11介导的代谢转化为癌症子集内的活性SCD抑制剂。在本文中，我们描述了草酸二酰胺和相关N-酰基脲的优化，以及与代谢活化和SCD抑制有关的结构-活性关系的分析。
• Synthesis of Dicarboxylic Acid Amides and Diamides on the Basis of [4-(4-Methoxyphenyl)tetrahydro-2H-pyran-4-yl]methanamine
  作者：A. A. Aghekyan、G. G. Mkryan、R. E. Muradyan、A. E. Tumajyan

  DOI：10.1134/s1070428018060106

  日期：2018.6

  ethyl N-[4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methyl}oxamate prepared from [4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methanamine and diethyl oxalate afforded the corresponding N,N'-disubstituted oxamides. N-Aryloxamides were synthesized by the reaction of [4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-yl]methanamine with ethyl N-aryloxamates. The condensation of N-[4-(4-methoxyphenyl)tetrah

  各种非芳族胺的用乙酸乙酯缩合ñ - [4-（4-甲氧基苯基）四氢-2 ħ -吡喃-4-基]甲基}从制备草氨酸乙酯[4-（4-甲氧基苯基）四氢-2 ħ -pyran- 4-基]甲胺和草酸二乙酯得到相应的N，N′-二取代的草酰胺。Ñ -Aryloxamides由[4-（4-甲氧基苯基）四氢-2的反应合成ħ -2H-吡喃-4-基]甲胺用乙酸乙酯Ñ -aryloxamates。的缩合ñ - [4-（4-甲氧基苯基）四氢-2 ħ -吡喃-4-基]甲基}琥珀酰胺酸与伯胺，得到Ñ，Ñ'-二取代的神经酰胺。
• Visible light-mediated photocatalytic oxidative cleavage of activated alkynes <i>via</i> hydroamination: a direct approach to oxamates
  作者：Narenderreddy Katta、Mamata Ojha、Arumugavel Murugan、Sagar Arepally、Duddu S. Sharada

  DOI：10.1039/c9ra10555g

  日期：——

  The direct oxidative cleavage of activated alkynes via hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an in situ formed enamine followed by radical coupling with an oxidant finally delivers the oxamate. The key features of this photocatalytic reaction are the mild reaction conditions

  已经描述了在室温下在可见光照射下使用有机光催化剂通过加氢胺化直接氧化裂解活化的炔烃。在该反应中，原位形成的烯胺的单电子氧化，然后与氧化剂自由基偶联，最终得到草酸盐。该光催化反应的主要特点是反应条件温和，无金属有机染料作为光催化剂，TBHP作为“O”源和光催化剂再生的双重作用。