Substituted 2,5'-bi-1H-benzimidazoles: Topoisomerase I inhibition and cytotoxicity

被引：264
|
作者：
Kim, JS
Gatto, B
Yu, C
Liu, A
Liu, LF
LaVoie, EJ
机构：
[1] RUTGERS STATE UNIV,DEPT PHARMACEUT CHEM,PISCATAWAY,NJ 08855
[2] UNIV MED & DENT NEW JERSEY,ROBERT WOOD JOHNSON MED SCH,DEPT PHARMACOL,PISCATAWAY,NJ 08855
来源：
JOURNAL OF MEDICINAL CHEMISTRY | 1996年 / 39卷 / 04期
关键词：
D O I：
10.1021/jm950412w
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.
引用
收藏
页码：992 / 998
页数：7
相关论文
共 50 条
  • [1] Synthesis and biological activity of novel inhibitors of topoisomerase I: 2-Aryl-substituted 2-bis-1H-benzimidazoles
    Singh, Manish
    Tandon, Vibha
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (02) : 659 - 669
  • [2] Topoisomerase I inhibition and cytotoxicity of 5-bromo- and 5-phenylterbenzimidazoles
    Rangarajan, M
    Kim, JS
    Sim, SP
    Liu, A
    Liu, LF
    LaVoie, EJ
    BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (11) : 2591 - 2600
  • [3] 2"-substituted 5-phenylterbenzimidazoles as topoisomerase I poisons
    Rangarajan, M
    Kim, JS
    Jin, S
    Sim, SP
    Liu, A
    Pilch, DS
    Liu, LF
    LaVoie, EJ
    BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (06) : 1371 - 1382
  • [4] 2H-BENZIMIDAZOLES (ISOBENZIMIDAZOLES) .3. THERMAL-ISOMERIZATION OF SUBSTITUTED 2H-BENZIMIDAZOLES TO 1H-BENZIMIDAZOLES
    HERBERT, JAL
    IDDON, B
    ROBINSON, AG
    SUSCHITZKY, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05): : 991 - 997
  • [5] Crystal structures of arylsulfonylation products of 2-alkyl-5-substituted-1H-benzimidazoles
    Okmanov, Rasul Ya
    Abdireymov, Kudaybergen B.
    Matchanova, Dinara R.
    Olimova, Manzura, I
    Turgunov, Kambarali K.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2022, 78 : 1271 - +
  • [6] SYNTHESIS OF 2,5(6)-DISUBSTITUTED-BENZIMIDAZOLES, 2-SUBSTITUTED-5-(4-SUBSTITUTED-PHENYL)-1,3,4-THIADIAZOLES AND IMIDAZOTHIOXANTHENE AND THEIR ANTIFILARIAL ACTIVITY
    CHAUHAN, PMS
    BHAKUNI, DS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (11): : 1146 - 1149
  • [7] Crystal and molecular structures of two 1H-2-substituted benzimidazoles
    Cabildo, Pilar
    Claramunt, Rosa M.
    Zuniga, Fco. Javier
    Alkorta, Ibon
    Elguero, Jose
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, 2015, 230 (06): : 427 - 438
  • [8] Chemistry of 2-substituted benzimidazoles. I. 5-amino-2-methyl(aryl, arylalkyl, pyridyl)benzimidazoles
    Ambacheu, KD
    Pleshakov, VG
    Baath, BS
    Zvolinskii, VP
    Kharlamova, MD
    Obynochnii, AA
    Prostakov, NS
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2000, (04): : 493 - 500
  • [9] Substituted benzimidazoles .1. Synthesis and properties of some 2-aryl-5-fluoro-6-(4-methyl-1-piperazinyl)-1H-benzimidazoles
    ElAbadelah, MM
    Sabri, SS
    Zarga, MHA
    AbdelJalil, RJ
    HETEROCYCLES, 1995, 41 (12) : 2713 - 2728
  • [10] 5-SUBSTITUTED AND 2,5-SUBSTITUTED 1,3-DIAZAAZULENES
    MURATA, I
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1961, 34 (04) : 580 - 585
12345