Convenient synthesis and antitumor evaluation of some new 9-ethyl-3-(hetaryl)carbazoles

被引:15
作者
Bondock, Samir [1 ,2 ]
Alqahtani, Salwa [3 ]
Fouda, Ahmed M. [1 ]
机构
[1] King Khalid Univ, Fac Sci, Chem Dept, Abha, Saudi Arabia
[2] Mansoura Univ, Fac Sci, Chem Dept, ET-35516 Mansoura, Egypt
[3] King Khalid Univ, Fac Sci & Arts, Chem Dept, Sarat Abidah, Saudi Arabia
关键词
Antitumor activity; carbazole; enaminonitrile; 2H-chromen-2-one; N-nucleophiles; 2-pyridone; ANTICANCER ACTIVITY; CARBAZOLE; COUMARIN; DERIVATIVES; INHIBITORS; CHEMISTRY; DESIGN; PROGRESS; AGENTS;
D O I
10.1080/00397911.2019.1616759
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In continuing our efforts to develop new potent anticancer candidates, a new series of 9-ethylcarbazoles carrying at position 3 various heterocyclic substituents such as 2-imino-2H-chromenes 5a-e, 2-oxo-2H-chromenes 6a-e, 3-imino-3H-benzo[f]chromene 8, 3-oxo-3H-benzo[f]chromene 9, 2-pyridones 11, 14, pyrazole 19, pyrimidine 23, pyrido[1,2-a]pyrimidine 27, 2H-pyran-2-one 30, and pyrano[2,3-d]pyrimidinetrione 34 were efficiently synthesized, characterized and evaluated for their in vitro antitumor activity. The mechanism for the synthesis of compounds was also discussed. Most of the synthesized compounds were displayed the considerable anticancer activities against three human tumor cells lines, in particular, colon carcinoma (HCT-116), hepatocellular carcinoma (HepG-2) and breast cancer (MCF-7). Compound 6d proves as most active molecule in this study with special effectiveness against the human HCT-116 and HepG-2 as its IC50 values are 1.50, 0.90 mu M, respectively, when doxorubicin is compared. Compound 34 was also found to have high activity against HepG-2, HCT-116 and moderate activity against MCF-7.
引用
收藏
页码:2188 / 2202
页数:15
相关论文
共 41 条
[11]   Recent Progress in the Synthesis and Applications of Heterocycles Derived from Enaminonitriles [J].
Bondock, Samir ;
Tarhoni, Abd El-Gaber ;
Fadda, Ahmed A. .
CURRENT ORGANIC CHEMISTRY, 2011, 15 (05) :753-781
[12]   Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative [J].
Devji, Tehsina ;
Reddy, Claire ;
Woo, Christina ;
Awale, Suresh ;
Kadota, Shigetoshi ;
Carrico-Moniz, Dora .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (19) :5770-5773
[13]   Current developments of coumarin-based anti-cancer agents in medicinal chemistry [J].
Emami, Saeed ;
Dadashpour, Sakineh .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 102 :611-630
[14]   Recent developments in chemical reactivity of N,N-dimethylenamino ketones as synthons for various heterocycles [J].
Gaber, Hatem M. ;
Bagley, Mark C. ;
Muhammad, Zeinab A. ;
Gomha, Sobhi M. .
RSC ADVANCES, 2017, 7 (24) :14562-14610
[15]   Biological potential of carbazole derivatives [J].
Gluszynska, Agata .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 94 :405-426
[16]   Anticancer carbazole alkaloids and coumarins from Clausena plants: A review [J].
Huang Li ;
Feng Zhe-Ling ;
Wang Yi-Tao ;
Lin Li-Gen .
CHINESE JOURNAL OF NATURAL MEDICINES, 2017, 15 (12) :881-888
[17]  
Ibrahim DA., 2016, ARKIVOC, V2016, P1, DOI [10.3998/ark.5550190.p009.722, DOI 10.3998/ARK.5550190.P009.722]
[18]  
Ibrahim HM, 2007, HETEROCYCLES, V71, P1951
[19]   Design, Synthesis and Evaluation of Novel 9-substituted Carbazole Derivatives as Potential Anticancer Agents [J].
Kumar, Nitin ;
Pathak, Devender .
LETTERS IN DRUG DESIGN & DISCOVERY, 2015, 12 (09) :760-765