5-amino-4-cyano-N-(4-chlorophenyl)-3-methylthiophene-2-carboxamide

• 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: 5-amino-4-cyano-N-(4-chlorophenyl)-3-methylthiophene-2-carboxamide
• 英文别名: 5-amino-N-(4-chlorophenyl)-4-cyano-3-methylthiophene-2-carboxamide
• 化学式: C₁₃H₁₀ClN₃OS
• 分子量: 291.761
• InChiKey: ANGCNBJQQNTRJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-4-cyano-N-(4-chlorophenyl)-3-methylthiophene-2-carboxamide 在 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-(4-chlorophenyl)-4-cyano-3-methyl-5-(2-(5-(phenylamino)-1,3,4-thiadiazol-2-ylthio)acetamido)thiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis of some new thiophene-based compounds and evaluations of their cytotoxic activities

  摘要：

  摘要通过前体 N-(4-取代苯基)-5-(2-氯乙酰氨基)-4-氰基-3-甲基噻吩-2-甲酰胺 4a 和 4b 与不同的硫和/或氮亲核试剂（即巯基乙酸、2-巯基苯并噻唑、5-（苯基氨基）-1,3,4-噻二唑-2-硫醇、2-巯基-4,6-二甲基烟腈、3-芳基偶氮-4-巯基-4-（苯基氨基）-丁-3-烯-酮衍生物、硫氰酸铵、哌啶和/或吗啉）。制备的噻吩化合物的结构通过光谱分析进行了表征。评估了它们对两种人类癌细胞系（HepG2 和 MCF-7）的细胞毒性，结果表明效果良好。用被测化合物 4b 预处理 HepG2 细胞可使细胞对索拉非尼的细胞毒性敏感，导致 IC50 从 3.9 µM 显著降至 0.5 µM； ； 关键词： N-(噻吩基)-2-氯乙酰胺 双噻吩 噻吩并[2,3-d]嘧啶 硫氰酸铵 细胞毒性 ； ； Bull.Chem.Soc.2023，37（2），373-389； DOI: https://dx.doi.org/10.4314/bcse.v37i2.10

  DOI：

  10.4314/bcse.v37i2.10
• 作为产物：
  描述：

  对氯苯胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 5-amino-4-cyano-N-(4-chlorophenyl)-3-methylthiophene-2-carboxamide
  参考文献：
  名称：

  EFFECTIVE MICROWAVE SYNTHESIS OF BIOACTIVE THIENO[2,3-d]PYRTMIDINES

  摘要：

  A series of novel 2-amino-3-cyanothiophenes (2a-2j) were synthesized using heterogeneous base (K2CO3) supported Gewald reaction. Cyclization of 2a-j with formamide and urea in conventional heating as well as microwave irradiation gave thieno[2,3-d]pyrimidines (3a-3j) and thieno[2,3-d]pyrimidin-2(1H)-ones(4a-4j) respectively. The reaction rates were faster and yields were higher in the microwave conditions. The structures of the compounds were confirmed with elemental analysis, mass spectral analysis, FTIR, H-1 NMR and C-13 NMR techniques. All the synthesized compounds were subjected to antimicrobial activity (MIC) in vitro by broth dilution method and exhibited a moderate antimicrobial activity.

  DOI：

  10.4067/s0717-97072017000100010

文献信息

• EFFECTIVE MICROWAVE SYNTHESIS OF BIOACTIVE THIENO[2,3-d]PYRTMIDINES
  作者：TASLIMAHEMAD T KHATRI、VIRESH H SHAH

  DOI：10.4067/s0717-97072017000100010

  日期：——

  A series of novel 2-amino-3-cyanothiophenes (2a-2j) were synthesized using heterogeneous base (K2CO3) supported Gewald reaction. Cyclization of 2a-j with formamide and urea in conventional heating as well as microwave irradiation gave thieno[2,3-d]pyrimidines (3a-3j) and thieno[2,3-d]pyrimidin-2(1H)-ones(4a-4j) respectively. The reaction rates were faster and yields were higher in the microwave conditions. The structures of the compounds were confirmed with elemental analysis, mass spectral analysis, FTIR, H-1 NMR and C-13 NMR techniques. All the synthesized compounds were subjected to antimicrobial activity (MIC) in vitro by broth dilution method and exhibited a moderate antimicrobial activity.
• Synthesis of some new thiophene-based compounds and evaluations of their cytotoxic activities
  作者：Fatima S. Mehdhar、Abdullah Y. A. Alzahrani、Ebrahim Abdel-Galil、Ghada E. Abdel-Ghani、Ali Saeed、Ehab Abdel-Latif

  DOI：10.4314/bcse.v37i2.10

  日期：——

  ABSTRACT. A series of new thiophene derivatives was prepared through nucleophilic substitution reactions of the precursor N-(4-substituted-phenyl)-5-(2-chloroacetamido)-4-cyano-3-methylthiophene-2-‎carboxamides 4a and 4b with different sulfur and/or nitrogen nucleophilic reagents (namely; mercaptoacetic acid, 2-mercaptobenzothiazole, 5-(phenylamino)-1,3,4-thiadiazole-2-thiol, 2-mercapto-4,6-dimethylnicotinonitrile, 3-arylazo-4-mercapto-4-(phenylamino)-but-3-en-one derivatives, ammonium thiocyanate, piperidine and/or morpholine). The structures of the prepared thiophene compounds were characterized by spectral analysis. Their cytotoxicity was evaluated against two human cancer cell lines (HepG2 and MCF-7) and indicated promising results. Pretreatment of HepG2 cells with the tested compound 4b sensitized the cells to the cytotoxicity of sorafenib, leading to a significant decrease in the IC50 from 3.9 to 0.5 µM.   KEY WORDS: N-(Thienyl)-2-chloroacetamide, Bis-thiophene, Thieno[2,3-d]pyrimidine, Ammonium thiocyanate, Cytotoxicity   Bull. Chem. Soc. Ethiop. 2023, 37(2), 373-389.                                                           DOI: https://dx.doi.org/10.4314/bcse.v37i2.10

  摘要通过前体 N-(4-取代苯基)-5-(2-氯乙酰氨基)-4-氰基-3-甲基噻吩-2-甲酰胺 4a 和 4b 与不同的硫和/或氮亲核试剂（即巯基乙酸、2-巯基苯并噻唑、5-（苯基氨基）-1,3,4-噻二唑-2-硫醇、2-巯基-4,6-二甲基烟腈、3-芳基偶氮-4-巯基-4-（苯基氨基）-丁-3-烯-酮衍生物、硫氰酸铵、哌啶和/或吗啉）。制备的噻吩化合物的结构通过光谱分析进行了表征。评估了它们对两种人类癌细胞系（HepG2 和 MCF-7）的细胞毒性，结果表明效果良好。用被测化合物 4b 预处理 HepG2 细胞可使细胞对索拉非尼的细胞毒性敏感，导致 IC50 从 3.9 µM 显著降至 0.5 µM； ； 关键词： N-(噻吩基)-2-氯乙酰胺 双噻吩 噻吩并[2,3-d]嘧啶 硫氰酸铵 细胞毒性 ； ； Bull.Chem.Soc.2023，37（2），373-389； DOI: https://dx.doi.org/10.4314/bcse.v37i2.10