Synthesis and Antiproliferative Activity of NewN-Acylhydrazone Derivatives Containing Benzothiazole and Indole Based Moiety

被引：19
作者：
Liu, Kai [1 ]
Ding, Yangyang [1 ]
Kang, Congmin [1 ]
机构：
[1] Qingdao Univ Sci & Technol, Coll Chem Engn, Qingdao 266042, Peoples R China
来源：
PHARMACEUTICAL CHEMISTRY JOURNAL | 2020年 / 54卷 / 04期
关键词：
synthesis; N-acylhydrazone; benzothiazole; indole based moiety; antiproliferative activity; BIOLOGICAL EVALUATION; PHARMACOLOGICAL EVALUATION; ANTIMICROBIAL ACTIVITY; TYROSINE KINASE; DESIGN; ANTITUMOR; AGENTS; ANTIMALARIAL; INHIBITORS;
D O I：
10.1007/s11094-020-02215-w
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Through a structure-based molecular hybridization strategy, a series of newN-acylhydrazone derivatives containing the benzothiazole and indole based moiety were designed, synthesized and screened forin vitroantiproliferative activity against Hep G2 cancer cell line. One compound (7a) exhibited excellent antiproliferative activity with IC(50)values of 0.78 mu M against Hep G2. In addition, C-5 substitutions of the indole ring of target compounds might be crucial for their cytotoxic activities. Additionally, the relative configuration of target compounds was confirmed as theEisomer. Further chemical manipulation of derivative 7a can make it possible to obtain new potential antitumor agents.
引用
收藏
页码：345 / 352
页数：8
相关论文
共 40 条
  • [1] Synthesis, Biological Evaluation and 2D-QSAR Study of Halophenyl Bis-Hydrazones as Antimicrobial and Antitubercular Agents
    Abdel-Aziz, Hatem A.
    Eldehna, Wagdy M.
    Fares, Mohamed
    Al-Rashood, Sara T. A.
    Al-Rashood, Khalid A.
    Abdel-Aziz, Marwa M.
    Soliman, Dalia H.
    [J]. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2015, 16 (04) : 8719 - 8743
  • [2] Anticonvulsant evaluation of clubbed indole-1,2,4-triazine derivatives: A synthetic approach
    Ahuja, Priya
    Siddiqui, Nadeem
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 80 : 509 - 522
  • [3] In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives
    Akhtar, Tashfeen
    Hameed, Shahid
    Al-Masoudi, Najim A.
    Loddo, Roberta
    La Colla, Paolo
    [J]. ACTA PHARMACEUTICA, 2008, 58 (02) : 135 - 149
  • [4] Synthesis of some thiazolyl aminobenzothiazole derivatives as potential antibacterial, antifungal and anthelmintic agents
    Amnerkar, Nikhil D.
    Bhusari, Kishore P.
    [J]. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2011, 26 (01) : 22 - 28
  • [5] Synthesis, molecular modelling studies and ADME prediction of benzothiazole clubbed oxadiazole-Mannich bases, and evaluation of their anti-diabetic activity through in vivo model
    Bhutani, Rubina
    Pathak, Dharam Pal
    Kapoor, Garima
    Husain, Asif
    Kant, Ravi
    Iqbal, Md. Azhar
    [J]. BIOORGANIC CHEMISTRY, 2018, 77 : 6 - 15
  • [6] N-acylhydrazone inhibitors of influenza virus PA endonuclease with versatile metal binding modes
    Carcelli, Mauro
    Rogolino, Dominga
    Gatti, Anna
    De Luca, Laura
    Sechi, Mario
    Kumar, Gyanendra
    White, Stephen W.
    Stevaert, Annelies
    Naesens, Lieve
    [J]. SCIENTIFIC REPORTS, 2016, 6
  • [7] Novel nicotinoyl pyrazoline derivates bearing N-methyl indole moiety as antitumor agents: Design, synthesis and evaluation
    Chen, Kun
    Zhang, Ya-Liang
    Fan, Jing
    Ma, Xiang
    Qin, Ya-Juan
    Zhu, Hai-Liang
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 156 : 722 - 737
  • [8] Novel amidino substituted benzimidazole and benzothiazole benzo[b]thieno-2-carboxamides exert strong antiproliferative and DNA binding properties
    Cindric, Maja
    Jambon, Samy
    Harej, Anja
    Depauw, Sabine
    David-Cordonnier, Marie-Helene
    Pavelic, Sandra Kraljevic
    Karminski-Zamola, Grace
    Hranjec, Marijana
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 136 : 468 - 479
  • [9] PEG-600: a facile and eco-friendly reaction medium for the synthesis of N-alkyl derivatives of indole-3-carboxyaldehyde
    Dubey, P. K.
    Venkatanarayana, M.
    [J]. GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (04) : 257 - 261
  • [10] Figueiredo LP, 2017, STRUCTURE, V1147, P226
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