(E)-3-(2-Fluoro-phenylcarbamoyl)-acrylic acid | 198879-80-0

• 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: (E)-3-(2-Fluoro-phenylcarbamoyl)-acrylic acid
• 英文别名: 4-[(2-Fluorophenyl)amino]-4-oxo-2-butenoic acid；4-(2-fluoroanilino)-4-oxobut-2-enoic acid
• CAS: 198879-80-0
• 化学式: C₁₀H₈FNO₃
• mdl: MFCD00029799
• 分子量: 209.177
• InChiKey: NVKBZXHSDUVZDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-Fluoro-phenylcarbamoyl)-acrylic acid 在 硫酸 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 4.0h， 生成 1-(2-氟苯基)-1H-吡咯-2,5-二酮
  参考文献：
  名称：

  N-芳族马来酰亚胺作为自由基光引发剂的评价：光物理和光聚合表征

  摘要：

  使用丙烯酸酯单体与各种 N-芳族马来酰亚胺组合制备可光聚合组合物。N-芳族马来酰亚胺分为两组：可以采用平面构象的组和不能采用平面构象的组。使用单晶 X 射线衍射光谱、激光闪光光解光谱、紫外-可见吸收光谱和光差扫描量热法对马来酰亚胺进行了表征。发现平面 N-芳族马来酰亚胺具有较低的相对激发态三重态产率，显示初级马来酰亚胺 UV 吸收带随溶剂极性的变化而显着偏移，并且在直接 UV 激发时不会引发自由基聚合。Twisted N-aromatic maleimides 具有较高的相对三重态产率，显示初级马来酰亚胺紫外吸收带的可忽略的偏移，具有溶剂极性，并在直接激发时引发自由基聚合。发现添加二苯甲酮会显着...

  DOI：

  10.1021/jp002811v
• 作为产物：
  描述：

  马来酸酐 、 2-氟苯胺 以 乙醚 为溶剂， 生成 (E)-3-(2-Fluoro-phenylcarbamoyl)-acrylic acid
  参考文献：
  名称：

  N-芳族马来酰亚胺作为自由基光引发剂的评价：光物理和光聚合表征

  摘要：

  使用丙烯酸酯单体与各种 N-芳族马来酰亚胺组合制备可光聚合组合物。N-芳族马来酰亚胺分为两组：可以采用平面构象的组和不能采用平面构象的组。使用单晶 X 射线衍射光谱、激光闪光光解光谱、紫外-可见吸收光谱和光差扫描量热法对马来酰亚胺进行了表征。发现平面 N-芳族马来酰亚胺具有较低的相对激发态三重态产率，显示初级马来酰亚胺 UV 吸收带随溶剂极性的变化而显着偏移，并且在直接 UV 激发时不会引发自由基聚合。Twisted N-aromatic maleimides 具有较高的相对三重态产率，显示初级马来酰亚胺紫外吸收带的可忽略的偏移，具有溶剂极性，并在直接激发时引发自由基聚合。发现添加二苯甲酮会显着...

  DOI：

  10.1021/jp002811v

文献信息

• The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation
  作者：Guowei Xu、Yaqing Yang、Yanming Yang、Gao Song、Shanshan Li、Jiajun Zhang、Weimin Yang、Liang-Liang Wang、Zhiying Weng、Zhili Zuo

  DOI：10.1016/j.ejmech.2020.112115

  日期：2020.4

  target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells

  腺苷酸环化酶（AC）在三磷酸腺苷（ATP）转化为第二信使环单磷酸腺苷（cAMP）的过程中起关键作用。研究表明2型腺苷酸环化酶（AC2）是许多疾病的潜在药物靶标，但是，到目前为止，尚无AC2选择性激动剂的报道。在这项研究中，已经进行了基于对接的虚拟筛选与基于细胞的生物学检测相结合，以发现新型有效的和选择性的AC2激动剂。虚拟筛选揭示了一种新型的命中化合物8，作为AC2激动剂，在重组人hAC2 + HEK293细胞上的EC50值为8.10μM。在重组AC2细胞上进一步研究了基于化合物8衍生物的SAR（结构活性关系），发现化合物73是最具活性的激动剂，EC50为90 nM，它比报道的激动剂福斯高林强160倍，并且可以选择性激活AC2以抑制白介素6的表达。新型AC2选择性激动剂的发现将为研究AC2的生理功能提供一种新颖的化学探针。
• Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents
  作者：Baihui Li、Yangli Shen、Hu Wu、Xiaobo Wu、Lvjiang Yuan、Qinggang Ji

  DOI：10.1016/j.ejmech.2020.112278

  日期：2020.6

  A series of 3,4-dihydro-2(1H)-quinolinone derivatives contained butenediamide fragment were designed and synthesized. Their inhibition potency against chitin synthase and antimicrobial activities were screened in vitro. The enzymatic assays showed that all the synthesized compounds had inhibition potency against chitin synthase at concentration of 300 μg/mL. Compound 2d displayed excellent potency

  设计合成了一系列含有丁烯二酰胺片段的3,4-二氢-2（1H）-喹啉酮衍生物。在体外筛选了它们对几丁质合酶的抑制能力和抗菌活性。酶促测定表明，所有合成的化合物在300μg/ mL的浓度下均具有针对甲壳质合酶的抑制能力。化合物2d表现出优异的效能，抑制百分数（IP）值为82.3％，而对照多恶菌素B的IP值为87.5％。IP值高于70％的化合物2b，2e和2s显示出对几丁质合酶的良好抑制能力。此外，2b的IC50值可与多恶英B（0.09 mM）相媲美。化合物2b的Ki为0.12 mM，Lineweaver-Burk图的结果表明2b是与甲壳质合酶结合的非竞争性抑制剂。抗真菌实验表明，这些化合物对真菌菌株，特别是白色念珠菌具有优异的抗真菌活性。化合物2b，2d，2e和2l对白念珠菌的抗真菌活性与氟康唑相当，并且优于多恶灵B。同时，其他化合物对白念珠菌的抗真菌活性也更好（MIC 2μg/ mL ）比化合物2n（MIC
• Unusual regio- and stereo-selectivity in Diels–Alder reactions between bulky N-phenylmaleimides and anthracene derivatives
  作者：Hao Chen、Erdong Yao、Chi Xu、Xiao Meng、Yuguo Ma

  DOI：10.1039/c4ob01052c

  日期：——

  Unusual regio- and stereo-selectivity in Diels–Alder (D–A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures

  Diels–Alder（D–A）反应中异常的区域选择性和立体选择性在庞大的N-苯基马来酰亚胺和蒽衍生物之间实现。使用在二烯和亲二烯体上都具有位阻的多个取代基，成功地获得了明显的向1，4-加成的转变。该反应中的底物范围广，抗-1,4-加合物的最高收率超过90％。通过单晶X射线衍射分析证实了抗-1,4-加合物的新颖结构。这项研究不仅提供了第一个报道的合成抗-1,4-加合物并获得了其他方式无法实现的区域和立体选择性，但同时也阐明了将两种反应物的空间效应相结合以使产物向1,4-加合物转化的重要性。此外，所得的1，4-加合物可以通过碳-碳偶合反应通过其卤素基团进一步官能化。
• Access to 8-Azabicyclo[3,2,1]octanes via the [3 + 2] Cycloaddition of Oxidopyridinium Ions to Maleimides
  作者：Cheng Yuan、Sheng Sun、Gangqiang Wang、Shaofa Sun、Jian Wang

  DOI：10.1021/acs.joc.3c00406

  日期：2023.7.7

  Herein, we reported a unique and operationally simple method to assemble 8-azabicyclo[3,2,1]octanes by using oxidopyridinium ions and maleimides as synthons. The features of good to high yields and good functional group tolerance are achieved regularly under mild conditions. Of note, oxidopyridinium ions undergo a [3 + 2] cycloaddition on their C2 and C6 positions.

  在此，我们报道了一种独特且操作简单的方法，通过使用氧化吡啶鎓离子和马来酰亚胺作为合成子来组装8-氮杂双环[3,2,1]辛烷。在温和的条件下通常可以实现良好的高产率和良好的官能团耐受性的特征。值得注意的是，氧化吡啶鎓离子在其 C2 和 C6 位置上发生 [3 + 2] 环加成。
• Design, synthesis, structure information and biochemical activity of new floro substituted organotin(IV) carboxylates
  作者：Farooq Ali Shah、Kaneez Fatima、Shaista Sabir、Saqib Ali、Ishtiaq Qadri、Noor ud din

  DOI：10.1016/j.jphotobiol.2015.10.011

  日期：2016.1

  Four new triorganotin(IV) complexes with general formula R3SnL (R = C4H9, C6H5, and L = 3-[(fluorophenylamido)]propenoic acid, 3-[(fluorophenylamido)]propanoic acid) were synthesized and characterized by elemental analyses, FT-IR, NMR (H-1, C-13 and Sn-119), mass spectrometry and single crystal X-ray structural analysis. The disappearance of the OH peak of the carboxylic acid in the FT-IR and NMR spectra of the compounds conform the formation of the compound and suggests that the complexation occurs via oxygen atoms of the carboxylate moiety. FT-IR date shows the bidentate nature of the carboxylate moiety of the ligand as the Av value in all complexes is less than 250. Crystallographic data for compound 2 showed that tin has distorted tetrahedral geometry with 433.42 degrees angle around the central tin atom. The compounds (1-4) bind to DNA, resulting hypochromism shifts in UV-visible spectroscopy suggesting an intercalative mode of interactions. The compound-DNA interaction results (UV-visible and Viscometery) encourage using the compounds against HCV. The compounds (1-4) were screened for anti-HCV activity using Huh7.5 cell (human hepatoma cell) by the Gaussia Luciferase Assay and found to be biologically active. Based on Gaussia Luciferase Assay, compound 3 (Tributylstannic [3-(2-fluorophenylamido)propionatel) was taken for quantitative analysis by "QRT-PCR" using the serum of HCV patients and was found to have substantial anti-HCV activity. This work, demonstrated that compound 3 may be used as a potential anti-HCV agent in the future. (C) 2015 Elsevier B.V. All rights reserved.