Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

被引:36
|
作者
Radi, Smaail [1 ]
Tighadouini, Said [1 ]
Feron, Olivier [2 ]
Riant, Olivier [3 ]
Bouakka, Mohammed [4 ]
Benabbes, Redouane [4 ]
Mabkhot, Yahia N. [5 ]
机构
[1] Univ Mohamed I, Fac Sci, Dept Chem, Oujda 60000, Morocco
[2] Catholic Univ Louvain, Angiogenesis & Canc Res Lab, Pole Pharmacol & Therapeutics FATH5349, Inst Expt & Clin Res, B-1200 Brussels, Belgium
[3] Catholic Univ Louvain, Mol Solids & React MOST, Inst Condensed Mater & Nanosci IMCN, B-1348 Louvain, Belgium
[4] Univ Mohamed I, Fac Sci, Dept Biol, Oujda 60000, Morocco
[5] King Saud Univ, Dept Chem, Fac Sci, Riyadh 11451, Saudi Arabia
来源
MOLECULES | 2015年 / 20卷 / 11期
关键词
keto-enols; heterocycles; breast cancer; fungal strains; CURCUMIN; ANALOGS; INTEGRATION; INHIBITORS;
D O I
10.3390/molecules201119684
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Recently, a new generation of highly promising inhibitors bearing -keto-enol functionality has emerged. Reported herein is the first synthesis and use of novel designed drugs based on the -keto-enol group embedded with heterocyclic moieties such as pyrazole, pyridine, and furan, prepared in a one-step procedure by mixed Claisen condensation. All the newly synthesized compounds were characterized by FT-IR, H-1-NMR, C-13-NMR, ESI/LC-MS, elemental analysis, and evaluated for their in vitro antiproliferative activity against breast cancer (MDA-MB241) human cell lines and fungal strains (Fusarium oxysporum f.sp albedinis FAO). Three of the synthesized compounds showed potent activity against fungal strains with IC50 values in the range of 0.055-0.092 mu M. The results revealed that these compounds showed better IC50 values while compared with positive controls.
引用
收藏
页码:20186 / 20194
页数:9
相关论文
共 50 条
  • [41] Design, Synthesis, and Biological Evaluation of Novel Amyl Ester Tethered Dihydroartemisinin-Isatin Hybrids as Potent Anti-Breast Cancer Agents
    Xu, Zhi
    Zhang, Xiaoyan
    Liu, Jie
    Zhao, Shijia
    Liu, Junna
    Zhou, Wei
    CHEMISTRY & BIODIVERSITY, 2023, 20 (03)
  • [42] New Trends of Acetonitrile Moiety in Heterocyclic Synthesis: Synthesis of Some Novel Pyrazole Derivatives as Antibacterial and Antifungal Agents
    El-Mekawy, Rasha E.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) : 2367 - 2374
  • [43] Synthesis and evaluation of new 3-substituted-4-chloro-thioxanthone derivatives as potent anti-breast cancer agents
    Chen, Chun-Liang
    Chen, Tsung-Chih
    Lee, Chia-Chung
    Shih, Liu-Chuan
    Lin, Chih-Yuan
    Hsieh, Ying-Yu
    Ali, Ahmed Atef Ahmed
    Huang, Hsu-Shan
    ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (08) : 3503 - 3516
  • [44] Design and Synthesis of Bioinspired Benzocoumarin-Chalcones Chimeras as Potential Anti-Breast Cancer Agents
    Saquib, Mohammad
    Baig, Mohammad Hassan
    Khan, Mohammad Faheem
    Azmi, Sarfuddin
    Khatoon, Shahnaaz
    Rawat, Arun Kumar
    Dong, Jae June
    Asad, Mohammad
    Arshad, Md
    Hussain, Mohd Kamil
    CHEMISTRYSELECT, 2021, 6 (33): : 8754 - 8765
  • [45] Synthesis of new Michael acceptors with cinnamamide scaffold as potential anti-breast cancer agents: cytotoxicity and ADME in silico studies
    Paulino, Ruth P.
    Alves, Rosemeire B.
    Silva, Heveline
    de Freitas, Rossimiriam P.
    MEDICINAL CHEMISTRY RESEARCH, 2024, 33 (11) : 2110 - 2121
  • [46] Cytotoxicity and gene expression profiles of novel synthesized steroid derivatives as chemotherapeutic anti-breast cancer agents
    Elmegeed, Gamal A.
    Khalil, Wagdy K. B.
    Mohareb, Rafat M.
    Ahmed, Hanaa H.
    Abd-Elhalim, Mervat M.
    Elsayed, Ghada H.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (22) : 6860 - 6872
  • [47] Neo-tanshinlactone inspired synthesis, in vitro evaluation of novel substituted benzocoumarin derivatives as potent anti-breast cancer agents
    Sashidhara, Koneni V.
    Rosaiah, Jammikuntla N.
    Kumar, Manoj
    Gara, Rishi Kumar
    Nayak, Lakshma Vadithe
    Srivastava, Kamini
    Bid, Hemant Kumar
    Konwar, Rituraj
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) : 7127 - 7131
  • [48] Novel ester tethered dihydroartemisinin-3-(oxime/thiosemicarbazide)isatin hybrids as potential anti-breast cancer agents: Synthesis, in vitro cytotoxicity and structure-activity relationship
    Liu, Shaohuan
    Wang, Shu
    Xu, Dan
    Pan, Bowen
    Chen, Linzhi
    Zhao, Shijia
    Xu, Zhi
    Zhou, Wei
    DRUG DEVELOPMENT RESEARCH, 2023, 84 (06) : 1175 - 1182
  • [49] Design and Synthesis of Novel Chalcone Derivatives: Anti-Breast Cancer Activity Evaluation and Docking Study
    Lai, Weihong
    Chen, Jiaxin
    Gao, Xinjiao
    Jin, Xiaobao
    Chen, Gong
    Ye, Lianbao
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (21)
  • [50] Synthesis and Antifungal Activities of Novel Griseofulvin Derivatives as Potential Anti-Phytopathogenic Fungi Agents
    Bai, Yu-Bin
    Yang, Kai-Ming
    Zhang, Meng
    Li, Yi-Xiang
    Zhao, Yu
    Huang, Liang-Zhu
    Yang, Hua
    Yang, Xiao-Jun
    Li, Ding
    Gao, Jin-Ming
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (23) : 13015 - 13022