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

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

  • Eur J Med Chem. 2014 May 6:78:151-6. doi: 10.1016/j.ejmech.2014.03.049.
Ali Ramazani 1,  Mehdi Khoobi 2,  Azar Torkaman 3,  Fatemeh Zeinali Nasrabadi 4,  Hamid Forootanfar 5,  Mojtaba Shakibaie 5,  Mandana Jafari 5,  Alieh Ameri 5,  Saeed Emami 6,  Mohammad Ali Faramarzi 7,  Alireza Foroumadi 2,  Abbas Shafiee 8
Affiliations

Affiliations

  • 1 Department of Chemistry, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran. Electronic address: aliramazani@gmail.com.
  • 2 Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
  • 3 Department of Chemistry, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran.
  • 4 Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
  • 5 Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran.
  • 6 Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
  • 7 Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran 14176, Iran.
  • 8 Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran. Electronic address: ashafiee@ams.ac.ir.
PMID: 24681979 DOI: 10.1016/j.ejmech.2014.03.049
Abstract

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 4.3 μM 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.

Keywords

1,3,4-Oxadiazole; Anti-cancer agents; Aza-Wittig reaction; Cytotoxic activity; Multi-component reactions.

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