Design, synthesis, and structure-activity relationship studies of benzothiazole derivatives as antifungal agents

被引：70
|
作者：
Zhao, Shizhen [1 ]
Zhao, Liyu [1 ]
Zhang, Xiangqian [1 ]
Liu, Chunchi [1 ]
Hao, Chenzhou [1 ]
Xie, Honglei [1 ]
Sun, Bin [2 ]
Zhao, Dongmei [1 ]
Cheng, Maosheng [1 ]
机构：
[1] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Minist Educ, Key Lab Struct Based Drug Design & Discovery, 103 Wenhua Rd, Shenyang 110016, Peoples R China
[2] Liaocheng Univ, Inst BioPharmaceut Res, 1 Hunan Rd, Liaocheng 252000, Peoples R China
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2016年 / 123卷
关键词：
Antifungal activity; Azole antifungals; CYP51; Structure-activity relationship; BIOLOGICAL EVALUATION; FUNGAL-INFECTIONS; CANDIDA-ALBICANS; DRUG-RESISTANCE;
D O I：
10.1016/j.ejmech.2016.07.067
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of compounds with benzothiazole and amide-imidazole scaffolds were designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. The antifungal activity of these compounds was evaluated in vitro, and their structure-activity relationships (SARs) were evaluated. The synthesized compounds showed excellent inhibitory activity against Candida albicans and Cryptococcus neoformans. The most potent compounds 14o, 14p, and 14r exhibited potent activity, with minimum inhibitory concentration (MIC) values in the range of 0.125-2 mu g/mL. Preliminary mechanism studies revealed that the compound 14p might act by inhibiting the CYP51 of Candida albicans. The SARs and binding mode established in this study are useful for further lead optimization. (C) 2016 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：514 / 522
页数：9
相关论文
共 50 条
  • [1] Design, Synthesis, and Structure-Activity Relationship Studies of Magnolol Derivatives as Antifungal Agents
    Li, Hu
    He, Ying-Hui
    Hu, Yong-Mei
    Chu, Qing-Ru
    Chen, Yong-Jia
    Wu, Zhen-Rong
    Zhang, Zhi-Jun
    Liu, Ying-Qian
    Yang, Cheng-Jie
    Liang, Hong-Jie
    Yan, Yin-Fang
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2021, 69 (40) : 11781 - 11793
  • [2] Discovery of biphenyl imidazole derivatives as potent antifungal agents: Design, synthesis, and structure-activity relationship studies
    Zhao, Dongmei
    Zhao, Shizhen
    Zhao, Liyu
    Zhang, Xiangqian
    Wei, Peng
    Liu, Chunchi
    Hao, Chenzhou
    Sun, Bin
    Su, Xin
    Cheng, Maosheng
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (02) : 750 - 758
  • [3] Design, Synthesis and Structure-Activity Relationship Studies of Nicotinamide Derivatives as Potent Antifungal Agents by Disrupting Cell Wall
    Ni, Tingjunhong
    Xie, Fei
    Li, Liping
    Hao, Yumeng
    Chi, Xiaochen
    Yan, Lan
    Zhang, Dazhi
    Jiang, Yuanying
    Lv, Quanzhen
    [J]. MOLECULES, 2023, 28 (03):
  • [4] Novel benzothiazole derivatives with a broad antifungal spectrum: design, synthesis and structure-activity relationships
    Liu, Yang
    Wang, Yan
    Dong, Guoqiang
    Zhang, Yongqiang
    Wu, Shanchao
    Miao, Zhenyuan
    Yao, Jianzhong
    Zhang, Wannian
    Sheng, Chunquan
    [J]. MEDCHEMCOMM, 2013, 4 (12) : 1551 - 1561
  • [5] Triazole derivatives as potential antifungal agents: A structure-activity relationship (SAR) studies
    Hu, Yuexiao
    Liu, Ziwei
    Zha, Gaofeng
    Long, Sihui
    Sridhara, M. B.
    Kumar, Kothanahally S. Sharath
    Rakesh, Kadalipura P.
    [J]. PROCESS BIOCHEMISTRY, 2023, 135 : 102 - 118
  • [6] Design, Synthesis, and Structure-Activity Relationship Studies of New Quinone Derivatives as Antibacterial Agents
    Andrades-Lagos, Juan
    Campanini-Salinas, Javier
    Pedreros-Riquelme, America
    Mella, Jaime
    Choquesillo-Lazarte, Duane
    Zamora, P. P.
    Pessoa-Mahana, Hernan
    Burbulis, Ian
    Vasquez-Velasquez, David
    [J]. ANTIBIOTICS-BASEL, 2023, 12 (06):
  • [7] Design, synthesis, and structure-activity relationship studies of L-amino alcohol derivatives as broad-spectrum antifungal agents
    Zhao, Liyu
    Tian, Linfeng
    Sun, Nannan
    Sun, Yin
    Chen, Yixuan
    Wang, Xinran
    Zhao, Shizhen
    Su, Xin
    Zhao, Dongmei
    Cheng, Maosheng
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 177 : 374 - 385
  • [8] Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents
    Wang, Guangcheng
    Wu, Wenshuang
    Peng, Fei
    Cao, Dong
    Yang, Zhuang
    Ma, Liang
    Qiu, Neng
    Ye, Haoyu
    Han, Xiaolei
    Chen, Jinying
    Qiu, Jingxiang
    Sang, Yun
    Liang, Xiaolin
    Ran, Yan
    Peng, Aihua
    Wei, Yuquan
    Chen, Lijuan
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 : 793 - 803
  • [9] Design, synthesis, and structure-activity relationship studies of novel tetrazole antifungal agents with potent activity, broad antifungal spectrum and high selectivity
    Qian, Anran
    Zheng, Yazhou
    Wang, Ruilian
    Wei, Jianhai
    Cui, Yongmei
    Cao, Xufeng
    Yang, Yushe
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2018, 28 (03) : 344 - 350
  • [10] Design, Synthesis, and Structure-Activity Relationship Studies of Tryptanthrins As Antitubercular Agents
    Hwang, Jae-Min
    Oh, Taegwon
    Kaneko, Takushi
    Upton, Anna M.
    Franzblau, Scott G.
    Ma, Zhenkun
    Cho, Sang-Nae
    Kim, Pilho
    [J]. JOURNAL OF NATURAL PRODUCTS, 2013, 76 (03): : 354 - 367
12345