Design, synthesis, and cytotoxic activities of new 2,4,5-triarylimidazoles

被引:2
|
作者
Zarghi, A. [1 ]
Arfaei, S. [1 ]
Shirazi, F. H. [2 ]
机构
[1] Shahid Beheshti Univ Med Sci, Sch Pharm, Dept Med Chem, Tehran, Iran
[2] Shahid Beheshti Univ Med Sci, Sch Pharm, Dept Toxicol, Tehran, Iran
关键词
Synthesis; 2,4,5-Triarylimidazoles; Cytotoxic activity; MTT; Docking study; BIOLOGICAL EVALUATION; ANTITUMOR-ACTIVITY; TAMOXIFEN; DOCKING; POTENT; PHARMACOKINETICS; DERIVATIVES; INHIBITORS; RECEPTOR; GROWTH;
D O I
10.1007/s00044-012-0391-5
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new group of 2,4,5-triarylimidazoles containing N,N-dimethylaminoethoxy or piperidinyl ethoxy group at the para position of the C-5 phenyl ring were synthesized and their cytotoxic activities were evaluated on three different breast cancer cell lines using MTT assay. The compounds contain various substituents at the para position of C-2 phenyl ring. Among the synthesized compounds, 4-(5-(4-(2-piperidin-1-yl)ethoxy)phenyl)-4-phenyl-1H-imidazol-2-yl)phenol (11e) and 1-2-(4-(2,4-diphenyl-1H-imidazol-5-yl)phenoxy)ethyl) piperidine (11h) with IC(50)s of less than 0.1 mu M on all three cell lines were the most potent cytotoxic compounds.
引用
收藏
页码:3897 / 3904
页数:8
相关论文
共 50 条
  • [1] Design, synthesis, and cytotoxic activities of new 2,4,5-triarylimidazoles
    A. Zarghi
    S. Arfaei
    F. H. Shirazi
    Medicinal Chemistry Research, 2013, 22 : 3897 - 3904
  • [2] A convenient synthesis of 2,4,5-triarylimidazoles catalyzed by Y(TFA)3
    Wang, Runxia
    Liu, Chunsheng
    Luo, Genxiang
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (02) : 101 - 104
  • [3] Metal Chloride Hydrates as Lewis Acid Catalysts in Multicomponent Synthesis of 2,4,5-Triarylimidazoles or 2,4,5-Triaryloxazoles
    Marques, Marcelo V.
    Ruthner, Marcelo M.
    Fontoura, Luiz A. M.
    Russowsky, Dennis
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (01) : 171 - U278
  • [4] One-Pot Synthesis of 2,4,5-Triarylimidazoles Catalyzed by Copper (II) Trifluoroacetate Under Solvent-Free Conditions
    Song, Dailei
    Liu, Chunsheng
    Zhang, Shaohua
    Luo, Genxiang
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2010, 40 (03) : 145 - 147
  • [5] Design and Synthesis of Pyrrolo[2,1-a]Isoquinoline-Based Derivatives as New Cytotoxic Agents
    Kakhki, Samaneh
    Shahosseini, Soraya
    Zarghi, Afshin
    IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH, 2016, 15 (04): : 743 - 751
  • [6] IONIC LIQUID MEDIATED ONE POT SYNTHESIS OF 2,4,5-TRIARYLIMIDAZOLES FROM 1,3-DIARYL PYARAZOLE CARBALDEHYDES UNDER SOLVENT-FREE CONDITION
    Shirole, Gopinath D.
    HETEROCYCLIC LETTERS, 2021, 11 (03): : 387 - 392
  • [7] Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles
    El-Gohary, Nadia S.
    Shaaban, Mona I.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 : 185 - 195
  • [8] Novel Pumice@SO3H catalyzed efficient synthesis of 2,4,5-triarylimidazoles and acridine-1,8-diones under microwave assisted solvent-free path
    Tambe, Adinath
    Gadhave, Anil
    Pathare, Akshay
    Shirole, Gopinath
    SUSTAINABLE CHEMISTRY AND PHARMACY, 2021, 22
  • [9] Design, Synthesis and Cytotoxic Activities of Novel Aliphatic Amino-Substituted Flavonoids
    Liu, Guannan
    Ge, Zhen
    Zhao, Mengdan
    Zhou, Yifeng
    MOLECULES, 2013, 18 (11) : 14070 - 14084
  • [10] Design, synthesis, and computational explorations of novel 2-thiohydantoin nucleosides with cytotoxic activities
    Khodair, Ahmed, I
    Bakare, Safyah B.
    Awad, Mohamed K.
    Al-Issa, Siham A.
    Nafie, Mohamed S.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (04) : 664 - 685