ethyl 3'-chloro-4'-fluorooxanilate | 69066-02-0

• 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
• 英文名称: ethyl 3'-chloro-4'-fluorooxanilate
• 英文别名: Ethyl [(3-chloro-4-fluorophenyl)amino](oxo)acetate；ethyl 2-(3-chloro-4-fluoroanilino)-2-oxoacetate
• CAS: 69066-02-0
• 化学式: C₁₀H₉ClFNO₃
• mdl: MFCD02859942
• 分子量: 245.638
• InChiKey: GBWFFCTYEWVGBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3'-chloro-4'-fluorooxanilate 在 水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 N¹-(3-chloro-4-fluorophenyl)-N²-((5-(2-hydroxyethyl)-4-methylthiazol-2-yl)(piperidin-2-yl)methyl)oxalamide dihydrochloride
  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：

  3-氯-4-氟苯胺 、 草酸二乙酯 以 甲苯 为溶剂， 反应 2.0h， 以89%的产率得到ethyl 3'-chloro-4'-fluorooxanilate
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of Oxanilates as Chemical Hybridizing Agents for Wheat (Triticum aestivum L.)

  摘要：

  Chemical hybridizing agents (CHAs) can facilitate two-line breeding in heterosis programs of crops. Twenty-seven oxanilates having different aromatic substitutions were synthesized and screened as CHAs on two genotypes of wheat, PBW 343 and HID 2733, during two Rabi (winter) seasons, 200001 and 2001-02. The oxanilates prepared by thermal condensation of anilines with diethyl oxalate or by acylation with ethoxycarbonyl methanoyl chloride were sprayed at 1000 and 1500 ppm at the premeiotic stage of wheat, when the length of the emerging spike of the first node was 7-8 mm. Pollen sterility and spikelet sterility were measured in each treatment. Ethyl oxanilates 5, 6, and 25, containing 4-F, 4-Br, and 4-CF3 aromatic substituents, respectively, induced greater than 98% spikelet sterility, the desired level, at 1500 ppm. Quantitative structure -activity relationship analysis revealed a direct relationship between F-p and molecular mass but an inverse relationship between MR, E-S, and R in influencing the bioactivity. Several F-1 hybrids were developed using 5, and at least one showed heterosis.

  DOI：

  10.1021/jf025870+

文献信息

• 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 and Antibacterial Activities of 2-<i>Oxo</i>-<i>N</i>-phenylacetamide Derivatives Containing a Dissulfone Moiety Target on Clp
  作者：Awei Zhang、Runjiang Song、Ronghua Wang、Hongde Li、Deyu Hu、Baoan Song

  DOI：10.1021/acs.jafc.2c02605

  日期：2022.8.3

  to the production of rice all over the world. To develop an efficient antibacterial agent with a novel target, a series of novel 2-oxo-N-phenylacetamide derivatives containing a dissulfone moiety were synthesized, and their antibacterial activities were evaluated. Among them, compound D14 exhibited the best antibacterial activities, especially against Xoo and Xoc with EC50 values of 0.63 and 0.79 mg/L

  水稻白叶枯病和水稻白条病是两种严重的水稻病害，对世界范围内的水稻生产造成了极大的危害。为了开发具有新靶点的高效抗菌剂，合成了一系列含有二砜部分的新型2-氧代-N-苯乙酰胺衍生物，并对其抗菌活性进行了评价。其中，化合物D 14表现出最好的抗菌活性，尤其是对Xoo和Xoc的抑菌活性， EC 50值分别为0.63和0.79 mg/L，明显优于商业对照的双甲基噻唑（BT ）。)（分别为 76.59 和 83.35 mg/L）和噻二唑铜 ( TC )（分别为 91.72 和 114.00 mg/L）。同时，化合物D 14可以与 Pxo99 A的 CRP 样蛋白 (Clp) 相互作用，并与Xoo -Clp表现出强结合活性， K d值为 0.52 μM，远优于BT的相应K d值。 183.94 μM ) 和TC (222.58 μM)。D 14的处理和clp基因的缺失可以显着降低clp的表达基因并减弱病原菌的毒力。这些结果表明化合物D
• Synthesis, Bioactivities, and Antibacterial Mechanism of 5-(Thioether)-<i>N</i>-phenyl/benzyl-1,3,4-oxadiazole-2-carboxamide/amine Derivatives
  作者：Awei Zhang、Hongfu He、Ronghua Wang、Zhongjie Shen、Zengxue Wu、Runjiang Song、Baoan Song

  DOI：10.1021/acs.jafc.3c05816

  日期：2024.1.24
• US4483707A
  申请人：——

  公开号：US4483707A

  公开（公告）日：1984-11-20
• Synthesis and Quantitative Structure−Activity Relationships of Oxanilates as Chemical Hybridizing Agents for Wheat (<i>Triticum aestivum </i>L.)
  作者：Kajal Chakraborty、Chakravarthi Devakumar、Shiv M. S. Tomar、Rajendra Kumar

  DOI：10.1021/jf025870+

  日期：2003.2.1

  Chemical hybridizing agents (CHAs) can facilitate two-line breeding in heterosis programs of crops. Twenty-seven oxanilates having different aromatic substitutions were synthesized and screened as CHAs on two genotypes of wheat, PBW 343 and HID 2733, during two Rabi (winter) seasons, 200001 and 2001-02. The oxanilates prepared by thermal condensation of anilines with diethyl oxalate or by acylation with ethoxycarbonyl methanoyl chloride were sprayed at 1000 and 1500 ppm at the premeiotic stage of wheat, when the length of the emerging spike of the first node was 7-8 mm. Pollen sterility and spikelet sterility were measured in each treatment. Ethyl oxanilates 5, 6, and 25, containing 4-F, 4-Br, and 4-CF3 aromatic substituents, respectively, induced greater than 98% spikelet sterility, the desired level, at 1500 ppm. Quantitative structure -activity relationship analysis revealed a direct relationship between F-p and molecular mass but an inverse relationship between MR, E-S, and R in influencing the bioactivity. Several F-1 hybrids were developed using 5, and at least one showed heterosis.