Design, synthesis, anti-proliferative activity, and molecular docking studies of novel benzo[f]chromene, chromeno [2,3-d]pyrimidines and chromenotriazolo[1,5-c]pyrimidines

被引:14
作者
Abu El-Azm, Fatma S. M. [1 ]
El-Shahawi, Manal M. [1 ]
Elgubbi, Amna S. [2 ]
Madkour, Hassan M. F. [1 ]
机构
[1] Ain Shams Univ, Fac Sci, Chem Dept, Khalifa El Maamon St,Abbasiya Sq, Cairo 11566, Egypt
[2] Misurata Univ, Fac Sci, Chem Dept, Misurata, Libya
关键词
Anti-proliferative activity; benzo[f]chromenes; benzo[f]chromeno[2; 3-d]pyrimidines; chromenotriazolo[1; 5-c]pyrimidines; molecular docking; RAPID COLORIMETRIC ASSAY; ANTIMICROBIAL ACTIVITY; HETEROCYCLIC-COMPOUNDS; BIOLOGICAL EVALUATION; ANTITUMOR; DERIVATIVES; INHIBITORS; DISCOVERY; EFFICIENT; SURVIVAL;
D O I
10.1080/00397911.2019.1710850
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In seeking to establish new anticancer agents, a group of novel substituted chromeno[2,3-d]pyrimidine and chromenotriazolo[1,5-c]pyrimidine derivatives were designed and synthesized as potential anti-proliferative agents. Chromeno[2,3-d]pyrimidine derivatives were prepared via reaction of ethyl formimidate derivative 2 with different nitrogen nucleophiles and chromenotriazolo[1,5-c]pyrimidine derivatives were obtained from treatment of cyanomethyl derivative 14 with various electrophilic reagents. The structures of the synthesized compounds were substantiated on the basis of spectral data and elemental analysis. All the synthesized products were evaluated for their antiproliferative activity against two human tumor cell lines; breast adenocarcinoma (MCF-7) and hepatocellular carcinoma (HepG-2) in addition to normal fibroblasts (WI-38). Derivatives 8 and 21 had significant and selective anti-proliferative activity against liver and breast cell lines without harming the normal fibroblasts. The molecular docking studies of most active compounds 8, 10, and 21 were performed to examine their binding pattern with protein receptors (PDB: 1SA0).
引用
收藏
页码:669 / 683
页数:15
相关论文
共 49 条
[1]  
Aaron J.-J., 2019, ENCY ANAL SCI, P432
[2]   Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives [J].
Abdelrazek, Fathy M. ;
Metz, Peter ;
Kataeva, Olga ;
Jaeger, Anne ;
El-Mahrouky, Sherif F. .
ARCHIV DER PHARMAZIE, 2007, 340 (10) :543-548
[3]   Synthesis, Anticancer Screening and Molecular Docking Studies of New Heterocycles with Trimethoxyphenyl Scaffold as Combretastatin Analogues [J].
Ali, Korany A. ;
Hafez, Naglaa A. Abdel ;
Elsayed, Mohamed A. ;
El-Shahawi, Manal M. ;
El-Hallouty, Salwa M. ;
Amr, Abd El-Galil E. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2018, 18 (08) :717-727
[4]   Synthesis and Antimicrobial Activity of Chromone-linked 2-Pyridone Fused with 1,2,4-Triazoles, 1,2,4-Triazines and 1,2,4-Triazepines Ring Systems [J].
Ali, Tarik El-Sayed ;
Ibrahim, Magdy Ahmed .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (06) :1007-1016
[5]   Discovery and Optimization of Chromenotriazolopyrimidines as Potent Inhibitors of the Mouse Double Minute 2-Tumor Protein 53 Protein-Protein Interaction [J].
Allen, John G. ;
Bourbeau, Matthew P. ;
Wohlhieter, G. Erich ;
Bartberger, Michael D. ;
Michelsen, Klaus ;
Hungate, Randall ;
Gadwood, Robert C. ;
Gaston, Rick D. ;
Evans, Bruce ;
Mann, Larry W. ;
Matison, Michael E. ;
Schneider, Stephen ;
Huang, Xin ;
Yu, Dongyin ;
Andrews, Paul S. ;
Reichelt, Andreas ;
Long, Alexander M. ;
Yakowec, Peter ;
Yang, Evelyn Y. ;
Lee, Tani Ann ;
Oliner, Jonathan D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (22) :7044-7053
[6]   Thieno[2,3-d]pyrimidines in the Synthesis of New Fused Heterocyclic Compounds of Prospective Antitumor and Antioxidant Agents (Part II) [J].
Aly, Ashraf A. ;
Ramadan, Mohamed ;
Mohamed, Ashraf M. ;
Ishak, Esam A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (05) :1009-1018
[7]  
[Anonymous], DASS SYST BIOVIA DIS
[8]   Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase [J].
Brühlmann, C ;
Ooms, F ;
Carrupt, PA ;
Testa, B ;
Catto, M ;
Leonetti, F ;
Altomare, C ;
Carotti, A .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (19) :3195-3198
[9]   Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives [J].
Chen, Qiong ;
Zhu, Xiao-Lei ;
Jiang, Li-Li ;
Liu, Zu-Ming ;
Yang, Guang-Fu .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :595-603
[10]   RAPID COLORIMETRIC ASSAY FOR CELL-GROWTH AND SURVIVAL - MODIFICATIONS TO THE TETRAZOLIUM DYE PROCEDURE GIVING IMPROVED SENSITIVITY AND RELIABILITY [J].
DENIZOT, F ;
LANG, R .
JOURNAL OF IMMUNOLOGICAL METHODS, 1986, 89 (02) :271-277