2-fluoroacrylamide | 1737-78-6

• 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: 2-fluoroacrylamide
• 英文别名: 2-Fluoroprop-2-enamide
• CAS: 1737-78-6
• 化学式: C₃H₄FNO
• mdl: MFCD03412234
• 分子量: 89.0693
• InChiKey: QLGUMAKHZODJET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-fluoroacrylamide 、 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以33.3%的产率得到2-fluoro-N-(3-((2-((1-methyl-1H-pyrazol-3-yl)amino)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-4-yl)oxy)phenyl)acrylamide
  参考文献：
  名称：

  Discovery of thiapyran-pyrimidine derivatives as potential EGFR inhibitors

  摘要：

  A series of novel thiapyran-pyrimidine derivatives (10a-10h, 11a-11g, 12a-12f, 13a-13f, 14a-14f) were synthesized and their antiproliferative activities were tested. Most of the target compounds showed good activity on one or more cancer cell lines but low activity on human normal cell LO2. The most promising compound 13a exhibited the similar IC50 values on A549 and H1975 cell lines to the lead drug Olmutinib, and exhibited excellent activity and selectivity on EGFR(T790M/L858R) in the kinase experiment. AO and Hoechst33258 staining indicated that 13a could effectively induce H1975 cells apoptosis. Cell cycle and apoptosis analysis suggested that 13a could block cancer cells in G2/M phase and induce into late apoptosis in a manner of concentration-dependent. The structure-activity relationship of 13a was analyzed to explore its mechanism. All the results showed that 13a was a promising EGFR inhibitor.

  DOI：

  10.1016/j.bmc.2020.115669
• 作为产物：
  描述：

  2,3-Dichlor-2-fluor-propansaeureamid 在 硫酸 、 水 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以27%的产率得到2-fluoroacrylamide
  参考文献：
  名称：

  合成vonα-Fluoracrylsäure和Derivaten

  摘要：

  Three new routes to derivatives of alpha-fluoracrylic acid, including a laboratory synthesis and a large-scale method, are reported. The processes are (i) addition of elementary fluorine to acrylic esters and subsequent elimination of HF; (ii) addition of difluorocarbene to isopropenyl methyl ether, oxidation via ring opening and dehalogenation; and (iii) 'nitrofluorination' of 2,3-dichloropropene, hydrolysis and dechlorination.

  DOI：

  10.1016/s0022-1139(00)80116-5

文献信息

• Design, Synthesis, and Antitumor Activity of Olmutinib Derivatives Containing Acrylamide Moiety
  作者：Xiaohan Hu、Sheng Tang、Feiyi Yang、Pengwu Zheng、Shan Xu、Qingshan Pan、Wufu Zhu

  DOI：10.3390/molecules26103041

  日期：——

  Two series of olmutinib derivatives containing an acrylamide moiety were designed and synthesized, and their IC50 values against cancer cell lines (A549, H1975, NCI-H460, LO2, and MCF-7) were evaluated. Most of the compounds exhibited moderate cytotoxic activity against the five cancer cell lines. The most promising compound, H10, showed not only excellent activity against EGFR kinase but also positive

  设计并合成了两个系列的含有丙烯酰胺部分的olmutinib衍生物，并评估了它们对癌细胞系的IC 50值（A549，H1975，NCI-H460，LO2和MCF-7）。大多数化合物对五种癌细胞系表现出中等的细胞毒活性。最有希望的化合物H10不仅显示出对EGFR激酶的出色活性，而且还显示出对PI3K激酶的积极生物学活性。结构-活性关系（SAR）表明，引入具有较小空间结构的二甲胺支架更有利于抗肿瘤活性。另外，不同丙烯酰胺侧链的取代对化合物的活性有不同的影响。通常，化合物H7H10和H10被证实是有希望的抗肿瘤药物。
• Design, synthesis and antitumor activity of novel thiophene-pyrimidine derivatives as EGFR inhibitors overcoming T790M and L858R/T790M mutations
  作者：Zhen Xiao、Zhihui Zhou、Cilong Chu、Qian Zhang、Lingjia Zhou、Zunhua Yang、Xin Li、Liying Yu、Pengwu Zheng、Shan Xu、Wufu Zhu

  DOI：10.1016/j.ejmech.2020.112511

  日期：2020.10

  Five series of novel thiophene-pyrimidine derivatives (9a-h, 10a-f, 11a-f, 12a-f, 13a-f) have been synthesized and tested for their anti-proliferative activity against several cancer cell lines in which EGF is highly expressed. Most of the target compounds showed excellent activity against one or more cancer cell lines. The most promising compound 13a, of which IC50 values on of cell lines A549 and

  已经合成了五种系列的新型噻吩-嘧啶衍生物（9a-h，10a-f，11a-f，12a-f，13a-f），并测试了其对几种癌细胞株的抗增殖活性，其中EGF含量很高。表达。大多数目标化合物对一种或多种癌细胞系均表现出优异的活性。最有前途的化合物13a在细胞系A549和A431上的IC 50值（4.34±0.60μM和3.79±0.57μM）与先导化合物Olmutinib相似，显示出对EGFR T790M和EGFR T790M / L858R的强活性和选择性。人类正常肝癌细胞株LO2的抑制数据表明，大多数目标化合物对正常细胞的毒性较小，并对癌细胞具有选择性抑制作用。此外，分析了结构-活性关系，并研究了13a诱导的细胞凋亡机制。结果表明，化合物13a以剂量依赖性方式诱导A431癌细胞的晚期凋亡。
• 10.1021/acs.orglett.4c01895
  作者：Bouzbouz, Samir

  DOI：10.1021/acs.orglett.4c01895

  日期：——

  A direct and simple catalytic coupling of nonfluorinated and fluorinated silylbutenamides with β-CF3 α,β-unsaturated esters mediated by fluoride ion was carried out. The transformation proceeded with excellent yields to afford new, highly functionalized trifluoromethylated and quaternary fluorinated products.

  在氟离子介导下，进行了非氟化和氟化甲硅烷基丁酰胺与β-CF 3 α,β-不饱和酯的直接且简单的催化偶联。该转化以优异的产率进行，提供了新的、高度官能化的三氟甲基化和四氟化产物。
• Sleptsova,O.M.; Koton,M.M., Journal of general chemistry of the USSR, 1960, vol. 30, p. 987 - 989
  作者：Sleptsova,O.M.、Koton,M.M.

  DOI：——

  日期：——
• Tolman,V.; Veres,K., Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 234 - 238
  作者：Tolman,V.、Veres,K.

  DOI：——

  日期：——