title: One-pot, four-component synthesis of novel cytotoxic agents 1-(5-aryl-1,3,4-oxadiazol-2-yl)-1-(1H-pyrrol-2-yl)methanamines.
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.
authors.affiliation: Department of Chemistry, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran. Electronic address: aliramazani@gmail.com.
authors.forename: Ali
authors.initials: A
authors.lastname: Ramazani
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
authors.forename: Mehdi
authors.initials: M
authors.lastname: Khoobi
authors.affiliation: Department of Chemistry, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran.
authors.forename: Azar
authors.initials: A
authors.lastname: Torkaman
authors.affiliation: Department of Chemistry, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran.
authors.forename: Fatemeh Zeinali
authors.initials: FZ
authors.lastname: Nasrabadi
authors.affiliation: Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran.
authors.forename: Hamid
authors.initials: H
authors.lastname: Forootanfar
authors.affiliation: Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran.
authors.forename: Mojtaba
authors.initials: M
authors.lastname: Shakibaie
authors.affiliation: Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran.
authors.forename: Mandana
authors.initials: M
authors.lastname: Jafari
authors.affiliation: Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran.
authors.forename: Alieh
authors.initials: A
authors.lastname: Ameri
authors.affiliation: Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran.
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.affiliation: Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran 14176, Iran.
authors.forename: Mohammad Ali
authors.initials: MA
authors.lastname: Faramarzi
authors.affiliation: Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
authors.affiliation: 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.
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006801:Humans; D061986:MCF-7 Cells; D008744:Methylamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D008744:Methylamines
keywords: 1,3,4-Oxadiazole; Anti-cancer agents; Aza-Wittig reaction; Cytotoxic activity; Multi-component reactions