Synthesis and Anticancer Activity Evaluation of New 1,2,4-Triazolyl-Quinazoline Hybrid Compounds and Their Pyrazolopyridine Analogs

被引:1
作者
Rahman, Adel A. -H. Abdel [1 ]
Sobhy, Asmaa [1 ]
Hawata, Mohamed A. [1 ]
Zayed, Ehab M. [2 ]
Awad, Hanem M. [3 ]
El-Sayed, Wael A. [4 ]
机构
[1] Menoufia Univ, Fac Sci, Chem Dept, Shibin Al Kawm, Egypt
[2] Natl Res Ctr, Green Chem Dept, 33 El Bohouth St,PO 12622, Giza, Egypt
[3] Natl Res Ctr, Tann & Leather Mat Dept, 33 El-Bohouth St,PO 12622, Giza, Egypt
[4] Natl Res Ctr, Photochem Dept, Giza, Egypt
来源
EGYPTIAN JOURNAL OF CHEMISTRY | 2024年 / 67卷 / 13期
关键词
quinazoline; triazolopyrimidine; triazolopyridine; hydrazide; anticancer; ANTIVIRAL EVALUATION; DERIVATIVES; 1,2,4-TRIAZOLES; INHIBITORS; DISCOVERY;
D O I
10.21608/ejchem.2024.257696.9043
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1,2,4-Triazolopyrimidinen and their isostericanalogs such as triazolopyridine have possessed their interest in, the literature, due to the reported broad spectrum of bioactivities, one of which is the anticancer activity. In the current study, new functionalized 1,2,4-triazoles-based substituted quinazolinesystems were prepared via multistep reactions starting from simple starting compounds. The reactions lead to the formation of the bi- and tricyclic 1,2,4-triazolopyridine and 1,2,4triazolopyrimidine compounds from the S-alkyl hydrazide, the ester and the hydrazine derivatives of the quinazoline system, respectively. The structures were characterized and confirmed by NMR, mass, and IR spectra. The anticancer activity revealed that several of the triazolopyrimidines-basedquinazoline structures especially those with theN-alkyl substitution in the quinazoline system were the most potent derivatives with results comparable to doxorubicin reference drug, the reference potent compound in the current investigation.
引用
收藏
页码:393 / 402
页数:10
相关论文
共 40 条
[21]  
Mishra S., A Review of Magnetically Recyclable Nanocatalysts for the Synthesis of Quinazoline and its Derivatives
[22]  
Mohamed MS, 2008, HETEROCYCL COMMUN, V14, P345
[23]   Methyl 2-((3-(3-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)thio)acetate [J].
Molnar, Maja ;
Komar, Mario ;
Jerkovic, Igor .
MOLBANK, 2022, 2022 (03)
[24]   Microwave assisted synthesis, antifungal activity, DFT and SAR study of 1,2,4-triazolo[4,3-a]pyridine derivatives containing hydrazone moieties [J].
Mu, Jin-Xia ;
Shi, Yan-Xia ;
Wu, Hong-Ke ;
Sun, Zhao-Hui ;
Yang, Ming-Yan ;
Liu, Xing-Hai ;
Li, Bao-Ju .
CHEMISTRY CENTRAL JOURNAL, 2016, 10
[25]   Discovery of pyrazolo[3,4-d]pyrimidine and pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as novel CDK2 inhibitors: synthesis, biological and molecular modeling investigations [J].
Nassar, Ibrahim F. ;
Aal, Mohammed T. Abdel ;
El-Sayed, Wael A. ;
Shahin, Mahmoud A. E. ;
Elsakka, Elsayed G. E. ;
Mokhtar, Mahmoud Mohamed ;
Hegazy, Maghawry ;
Hagras, Mohamed ;
Mandour, Asmaa A. ;
Ismail, Nasser S. M. .
RSC ADVANCES, 2022, 12 (23) :14865-14882
[26]   A Dicationic Molten Salt Catalyzed Synthesis of 1,2,4-Triazolopyrimidine, Quinazolinone and Biscoumarin Derivatives under Green Conditions [J].
Nazari, Shadi ;
Zabihzadeh, Mehdi ;
Shirini, Farhad ;
Tajik, Hassan .
POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (02) :1524-1535
[27]   Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds [J].
Nguyen, Cong T. ;
Nguyen, Quang T. ;
Dao, Phuc H. ;
Nguyen, Thuan L. ;
Nguyen, Phuong T. ;
Nguyen, Hung H. .
JOURNAL OF CHEMISTRY, 2019, 2019
[28]   Synthesis, Docking Studies into CDK-2 and Anticancer Activity of New Derivatives Based Pyrimidine Scaffold and Their Derived Glycosides [J].
Rahman, Adel A. H. Abdel ;
Nassar, Ibrahim F. ;
Shaban, Amira K. F. ;
EL-Kady, Dina S. ;
Awad, Hanem M. ;
El Sayed, Wael A. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2019, 19 (13) :1093-1110
[29]   Design, synthesis, and biological evaluation of tetrahydroquinolinones and tetrahydroquinolines with anticancer activity [J].
Ryczkowska, Malgorzata ;
Maciejewska, Natalia ;
Olszewski, Mateusz ;
Witkowska, Milena ;
Makowiec, Slawomir .
SCIENTIFIC REPORTS, 2022, 12 (01)
[30]   Hypervalent iodine mediated synthesis of 1-aryl/hetryl-1,2,4-triazolo[4,3-a] pyridines and 1-aryl/hetryl 5-methyl-1,2,4-triazolo[4,3-a]quinolines as antibacterial agents [J].
Sadana, AK ;
Mirza, Y ;
Aneja, KR ;
Prakash, O .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (05) :533-536