Synthesis, molecular modeling study, preliminary antibacterial, and antitumor evaluation of N-substituted naphthalimides and their structural analogues

被引：34
|
作者：
El-Azab, Adel S. [1 ,2 ]
Alanazi, Amer M. [1 ]
Abdel-Aziz, Naglaa I. [3 ]
Al-Suwaidan, Ibrahim A. [1 ]
El-Sayed, Magda A. A. [4 ]
El-Sherbeny, Magda A. [3 ]
Abdel-Aziz, Alaa A. -M. [1 ,3 ]
机构：
[1] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
[2] Al Azhar Univ, Dept Organ Chem, Fac Pharm, Cairo 11884, Egypt
[3] Univ Mansoura, Dept Med Chem, Fac Pharm, Mansoura 35516, Egypt
[4] Univ Mansoura, Dept Organ Pharmaceut Chem, Fac Pharm, Mansoura 35516, Egypt
来源：
MEDICINAL CHEMISTRY RESEARCH | 2013年 / 22卷 / 05期
关键词：
Naphthalimides; Cyclic imides; Synthesis; Antibacterial activity; Antitumor evaluation; Molecular modeling; Modeling; NATIONAL-CANCER-INSTITUTE; CYCLIC-IMIDES; ANTIINFLAMMATORY ACTIVITY; BIOLOGICAL EVALUATION; DRUG DISCOVERY; DNA-BINDING; INHIBITORS; DERIVATIVES; ACID; DESIGN;
D O I：
10.1007/s00044-012-0230-8
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Carboxylic acid imides 1-26 have been synthesized and screened for their antibacterial against gram-positive and gram-negative organisms and their antitumor activity against 60 tumor cell lines taken from nine different organs. Compounds 12, 14, and 16 were the most active and broad-spectrum antibacterial member in this study. Compound 9 showed the most cytotoxicity with a significant inhibition for renal cancer cells. 2D-QSAR study provides details on the fine relationship linking structure and activity and offers clues for structural modifications that can improve the activity. Docking study of the compounds 12, 14, and 16 into the active site of the topoisomerase II DNA gyrase enzymes revealed a similar binding mode to bound inhibitor Clorobiocin.
引用
收藏
页码：2360 / 2375
页数：16
相关论文
共 50 条
  • [41] Synthesis and Structural Characterization of Haloaryl N-Substituted Sugar Derivatives
    Rengel, Natividad Bejarano
    Esteche, Juliana
    Echeverria, Gustavo A.
    Piro, Oscar E.
    Santiago, Cintia C.
    Ponzinibbio, Agustin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [42] SYNTHESIS, CHARACTERIZATION AND ANALGESIC ACTIVITY OF SEVERAL NEW N-SUBSTITUTED PHTHALIMIDE ANALOGUES
    Fhid, Omran
    Saad, Shaban E. A.
    Zeglam, Talal H.
    Eswayah, Asma
    Baki, Jamal
    Alnnas, Esra
    Haroon, Yousra
    Zitouni, Majda
    Sdera, Wafa
    INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2014, 5 (08): : 3199 - 3203
  • [43] Synthesis and antitumor activity of novel N-substituted carbazole imidazolium salt derivatives
    Lan-Xiang Liu
    Xue-Quan Wang
    Bei Zhou
    Li-Juan Yang
    Yan Li
    Hong-Bin Zhang
    Xiao-Dong Yang
    Scientific Reports, 5
  • [44] Synthesis and antitumor activity of novel N-substituted carbazole imidazolium salt derivatives
    Liu, Lan-Xiang
    Wang, Xue-Quan
    Zhou, Bei
    Yang, Li-Juan
    Li, Yan
    Zhang, Hong-Bin
    Yang, Xiao-Dong
    SCIENTIFIC REPORTS, 2015, 5
  • [45] Structural Requirements of N-Substituted Spiropiperidine Analogues as Agonists of Nociceptin/Orphanin FQ Receptor
    Bao, Pingping
    Zhang, Xiaole
    Ren, Hong
    Li, Yan
    Mu, Zulin
    Zhang, Shuwei
    Li, Guohui
    Yang, Ling
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2011, 12 (12): : 8961 - 8981
  • [46] Design and synthesis of N-substituted acridone derivatives as potential antibacterial and antiviral agents
    Jimenez Sanchez, Liliana
    Juan-Guadarrama, Dante G.
    Loza-Mejia, Marco A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [47] Synthesis of Some New N-Substituted Imidazole Derivatives and Their In Vitro Antibacterial Investigation
    V. Sudheer Reddy
    N. Rajashekar Reddy
    A. Venkatram Reddy
    M. Padma
    L. Krishnakanth Reddy
    Russian Journal of Bioorganic Chemistry, 2022, 48 : 643 - 650
  • [48] Synthesis of Some New N-Substituted Imidazole Derivatives and Their In Vitro Antibacterial Investigation
    Reddy, V. Sudheer
    Reddy, N. Rajashekar
    Reddy, A. Venkatram
    Padma, M.
    Reddy, L. Krishnakanth
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2022, 48 (03) : 643 - 650
  • [49] SYNTHESIS AND BIOLOGICAL EVALUATION OF N-SUBSTITUTED POLYCYCLIC IMIDES DERIVATIVES
    Bielenica, Anna
    Struga, Marta
    Miroslaw, Barbara
    Koziol, Anna E.
    Kossakowski, Jerzy
    Sanna, Giuseppina
    La Colla, Paolo
    Giliberti, Gabriele
    ACTA POLONIAE PHARMACEUTICA, 2013, 70 (05): : 809 - 822
  • [50] SYNTHESIS AND EVALUATION OF THE ANALGESIC AND ANTIINFLAMMATORY ACTIVITIES OF N-SUBSTITUTED SALICYLAMIDES
    DAIDONE, G
    RAFFA, D
    PLESCIA, S
    MATERA, M
    CARUSO, A
    LEONE, V
    AMICOROXAS, M
    FARMACO, 1989, 44 (05): : 465 - 473
12345