N-(3-amino-4-fluorophenyl)benzamide | 866023-58-7

• 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: N-(3-amino-4-fluorophenyl)benzamide
• CAS: 866023-58-7
• 化学式: C₁₃H₁₁FN₂O
• 分子量: 230.242
• InChiKey: PXDSPSVHSIFKEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-(3-amino-4-fluorophenyl)benzamide 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  [EN] CATIONIC IMIDAZOLAZO DYES CONTAINING A 2, 5-DIAMINOPHENYL MOIETY
  [FR] COLORANTS AZOIQUES A SUBSTITUTION 2,5-DIAMINO

  摘要：

  公开号：

  WO2005095522A3
• 作为产物：
  描述：

  苯甲酸 在 光气 、 aluminum (III) chloride 、 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 N-(3-amino-4-fluorophenyl)benzamide
  参考文献：
  名称：

  Metabolically Stable Dibenzo[b,e]oxepin-11(6H)-ones as Highly Selective p38 MAP Kinase Inhibitors: Optimizing Anti-Cytokine Activity in Human Whole Blood

  摘要：

  Five series of metabolically stable disubstituted dibenzo[b,e]oxepin-11(6H)-ones were synthesized and tested in a p38 alpha enzyme assay for their inhibition of tumor necrosis factor-alpha (TNF-alpha) release in human whole blood. Compared to the monosubstituted dibenzo[b,e]oxepin-11(6H)-one derivatives, it has been shown that the additional introduction of hydrophilic residues at position 9 leads to a substantial improvement of the inhibitory potency and metabolic stability. Using protein Xray crystallography, the binding mode of the disubstituted dibenzoxepinones and the induction of a glyince flip in the hinge region were confirmed. The most potent compound of this series, 32e, shows an outstanding biological activity on isolated p38 alpha, with an IC50 value of 1.6 nM, extraordinary selectivity (by a factor >1000, Kinase WholePanelProfiler), and low ATP competitiveness. The ability to inhibit the release of TNF-alpha from human whole blood was optimized down to an IC50 value of 125 nM. With the promising dibenzoxepinone inhibitor 3i, a pharmacokinetic study in mice was conducted.

  DOI：

  10.1021/jm401276h

文献信息

• Discovery of Potent and Noncovalent Reversible EGFR Kinase Inhibitors of EGFR^{L858R/T790M/C797S}
  作者：Qiannan Li、Tao Zhang、Shiliang Li、Linjiang Tong、Junyu Li、Zhicheng Su、Fang Feng、Deheng Sun、Yi Tong、Xia Wang、Zhenjiang Zhao、Lili Zhu、Jian Ding、Honglin Li、Hua Xie、Yufang Xu

  DOI：10.1021/acsmedchemlett.8b00564

  日期：2019.6.13

  reversible epidermal growth factor receptor inhibitors of EGFRL858R/T790M/C797S. One of the most promising compounds, 25g, inhibited the enzymatic activity of EGFRL858R/T790M/C797S with an IC50 value of 2.2 nM. Cell proliferation assays showed that 25g effectively and selectively inhibited the growth of EGFRL858R/T790M/C797S-dependent cells. This series of compounds, which occupy both the ATP binding site

  在本文中，我们描述了一系列EGFR L858R / T790M / C797S的非共价可逆表皮生长因子受体抑制剂的发现和优化。最有前途的化合物之一25g抑制EGFR L858R / T790M / C797S的酶活性，IC 50值为2.2 nM。细胞增殖测定表明25g有效和选择性地抑制EGFR L858R / T790M / C797S依赖性细胞的生长。该系列化合物同时占据EGFR激酶的ATP结合位点和变构位点，可以作为开发针对L858R / T790M / C797S突变体的第四代EGFR抑制剂的基础。
• Targeting the Hinge Glycine Flip and the Activation Loop: Novel Approach to Potent p38α Inhibitors
  作者：Kathrin E. Martz、Angelika Dorn、Benjamin Baur、Verena Schattel、Márcia I. Goettert、Svenja C. Mayer-Wrangowski、Daniel Rauh、Stefan A. Laufer

  DOI：10.1021/jm300951u

  日期：2012.9.13

  The p38 MAP kinase is a key player in signaling pathways regulating the biosynthesis of inflammatory cytokines. Small molecule p38 inhibitors suppress the production of these cytokines. Therefore p38 is a promising drug target for novel anti-inflammatory drugs. In this study, we report novel dibenzepinones, dibenzoxepines, and benzosuberones as p38 alpha MAP kinase inhibitors. Previously reported dibenzepinones and dibenzoxepines were chemically modified by introduction of functional groups or removal of a phenyl ring. This should result in targeting of the hydrophobic region I, the "deep pocket", and the hinge glycine flip of the kinase. Potent inhibitors with IC50 values in the single digit nanomolar range (up to 3 nM) were identified. Instead of targeting the "deep pocket" in the DFG-out conformation, interactions with the DFG-motif in the in-conformation could be observed by protein X-ray crystallography.
• Copper-Catalyzed Synthesis of Benzoxazoles via a Regioselective C−H Functionalization/C−O Bond Formation under an Air Atmosphere
  作者：Satoshi Ueda、Hideko Nagasawa

  DOI：10.1021/jo900513z

  日期：2009.6.5

  An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160 degrees C allows the use of air as the tern-final oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.
• Acylthiourea, Acylurea, and Acylguanidine Derivatives with Potent Hedgehog Inhibiting Activity
  作者：Antonio Solinas、Hélène Faure、Hermine Roudaut、Elisabeth Traiffort、Angèle Schoenfelder、André Mann、Fabrizio Manetti、Maurizio Taddei、Martial Ruat

  DOI：10.1021/jm2013369

  日期：2012.2.23

  The Smoothened (Smo) receptor is the major transducer of the Hedgehog (Hh) signaling pathway. On the basis of the structure of the acylthiourea Smo antagonist (MRT-10), a number of different series of analogous compounds were prepared by ligand-based structural optimization. The acylthioureas, originally identified as actives, were converted into the corresponding acylureas or acylguanidines. In each series, similar structural trends delivered potent compounds with IC50 values in the nanomolar range with respect to the inhibition of the Hh signaling pathway in various cell-based assays and of BODIPY-cyclopamine binding to human Smo. The similarity of their biological activities, in spite of discrete structural differences, may reveal the existence of hydrogen-bonding interactions between the ligands and the receptor pocket. Biological potency of compounds 61, 72, and 86 (MRT-83) were comparable to those of the clinical candidate GDC-0449. These findings suggest that these original molecules will help delineate Smo and Hh functions and can be developed as potential anticancer agents.
• [EN] DISULFIDE DYES, COMPOSITION COMPRISING THEM AND METHOD OF DYEING HAIR<br/>[FR] COLORANTS A BASE DE SULFIDE
  申请人：CIBA SC HOLDING AG

  公开号：WO2005097051A3

  公开（公告）日：2005-12-15