N-benzyl-1-[5-(2,4-dichloro-5-fluorophenyl)-1,3,4-oxadiazol-2-yl]-1-(1H-pyrrol-2-yl)methanamine | 1607471-86-2

• 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-benzyl-1-[5-(2,4-dichloro-5-fluorophenyl)-1,3,4-oxadiazol-2-yl]-1-(1H-pyrrol-2-yl)methanamine
• CAS: 1607471-86-2
• 化学式: C₂₀H₁₅Cl₂FN₄O
• 分子量: 417.27
• InChiKey: ANQZUKMYUXTCOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-吡咯甲醛 、 (异氰亚氨基)三苯基膦 、 苄胺 、 2,4-二氯-5-氟苯甲酸 以 二氯甲烷 为溶剂， 反应 12.25h， 以86%的产率得到N-benzyl-1-[5-(2,4-dichloro-5-fluorophenyl)-1,3,4-oxadiazol-2-yl]-1-(1H-pyrrol-2-yl)methanamine
  参考文献：
  名称：

  One-pot, four-component synthesis of novel cytotoxic agents 1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines

  摘要：

  A series of N-benzyl-1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines were synthesized via one-pot reaction of appropriate benzylamine, pyrrole-2-carbaldehyde, (N-isocyanimino)triphenylphosphorane, and a carboxylic acid. The anti-tumor potential of title compounds was tested against several cancer cell lines by using MTT assay. Some tested compounds including 5e, 5p and 5q exhibited comparable or better cytotoxic activity against A549, HT29 or HT1080 cells in comparison to the reference drug doxorubicin. Also, the cytotoxic activity of compounds 5d and 5n against MCF-7 was better than that of doxorubicin. Compound 5n with IC50 value of 43 mu M was 4-fold more potent than doxorubicin. The structure-activity relationship study revealed that the introduction of halogen atoms on both 5-phenyl ring and N-benzyl part improved the cytotoxic activity against all tested cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.049

文献信息

• One-pot, four-component synthesis of novel cytotoxic agents 1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines
  作者：Ali Ramazani、Mehdi Khoobi、Azar Torkaman、Fatemeh Zeinali Nasrabadi、Hamid Forootanfar、Mojtaba Shakibaie、Mandana Jafari、Alieh Ameri、Saeed Emami、Mohammad Ali Faramarzi、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2014.03.049

  日期：2014.5

  A series of N-benzyl-1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines were synthesized via one-pot reaction of appropriate benzylamine, pyrrole-2-carbaldehyde, (N-isocyanimino)triphenylphosphorane, and a carboxylic acid. The anti-tumor potential of title compounds was tested against several cancer cell lines by using MTT assay. Some tested compounds including 5e, 5p and 5q exhibited comparable or better cytotoxic activity against A549, HT29 or HT1080 cells in comparison to the reference drug doxorubicin. Also, the cytotoxic activity of compounds 5d and 5n against MCF-7 was better than that of doxorubicin. Compound 5n with IC50 value of 43 mu M was 4-fold more potent than doxorubicin. The structure-activity relationship study revealed that the introduction of halogen atoms on both 5-phenyl ring and N-benzyl part improved the cytotoxic activity against all tested cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.