DABCO-catalyzed one-pot three component synthesis of dihydropyrano[3,2-c]chromene substituted quinazolines and their evaluation towards anticancer activity

被引:25
作者
Vodnala, Sumathi [1 ]
Bhavani, A. K. D. [1 ]
Kamutam, Ramakrishna [1 ]
Naidu, V. G. M. [2 ]
Promila [3 ]
Prabhakar, Ch. [3 ]
机构
[1] Osmania Univ, Univ Coll Sci, Dept Chem, Hyderabad 500004, Andhra Pradesh, India
[2] Natl Inst Pharmaceut Educ & Res NIPER, Hyderabad, Andhra Pradesh, India
[3] Natl Inst Technol, Dept Chem, Kurukshetra 36119, Haryana, India
关键词
Multicomponent reaction; Knoevenagel-Michael reaction; Quinazoline; 4-Hydroxycoumarin; DABCO; Anti-cancer; DISCOVERY; DERIVATIVES; ANTAGONISTS; INHIBITORS; ALKALOIDS; CHEMISTRY; RECEPTOR; AGENTS;
D O I
10.1016/j.bmcl.2016.07.003
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A facile DABCO promoted one-pot three component synthesis of a new series of C-C linked bis-hetero-cycle containing dihydropyrano[c]chromene as highly fused oxa-heteryl group at C-2 position of quinazoline was developed. Quinazoline-2-carbaldehyde, substituted 4-hydroxycoumarin and ethyl cyanoacetate were used as key components in the Knoevenagel-Michael addition reaction to get the titled compounds. These compounds were screened for anti-cancer activity against the breast cancer cell lines of MDA-MB 231, and MDA-MB 453. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3973 / 3977
页数:5
相关论文
共 26 条
[1]  
Artizzu N, 1995, FARMACO, V50, P853
[2]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[3]   Discovery of potent LPA2 (EDG4) antagonists as potential anticancer agents [J].
Beck, Hilary P. ;
Kohn, Todd ;
Rubenstein, Steven ;
Hedberg, Christine ;
Schwandner, Ralf ;
Hasslinger, Kerstin ;
Dai, Kang ;
Li, Cong ;
Liang, Lingining ;
Wesche, Holger ;
Frank, Brendon ;
An, Songhzu ;
Wckramasinghe, Dineli ;
Jaen, Juan ;
Medina, Julio ;
Hungate, Randall ;
Shen, Wang .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :1037-1041
[4]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 4-(1,2-DIHYDRO-2-OXO-1-PYRIDYL)-2H-1-BENZOPYRANS AND RELATED-COMPOUNDS, NEW POTASSIUM CHANNEL ACTIVATORS [J].
BERGMANN, R ;
GERICKE, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :492-504
[5]   SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 2-OXO-(2H) 1-BENZOPYRAN-3-CARBOXAMIDE DERIVATIVES [J].
BONSIGNORE, L ;
LOY, G ;
SECCI, D ;
CALIGNANO, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1993, 28 (06) :517-520
[6]   Structural and mechanistic insights into bisphenols action provide guidelines for risk assessment and discovery of bisphenol A substitutes [J].
Delfosse, Vanessa ;
Grimaldi, Marina ;
Pons, Jean-Luc ;
Boulahtouf, Abdelhay ;
le Maire, Albane ;
Cavailles, Vincent ;
Labesse, Gilles ;
Bourguet, William ;
Balaguer, Patrick .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (37) :14930-14935
[7]   Discovery of novel potent and selective ligands for 5-HT2A receptor with quinazoline scaffold [J].
Deng, Xinxian ;
Guo, Lin ;
Xu, Lili ;
Zhen, Xuechu ;
Yu, Kunqian ;
Zhao, Weili ;
Fu, Wei .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (18) :3970-3974
[8]   Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: Molecular docking study [J].
El-Azab, Adel S. ;
Al-Omar, Mohamed A. ;
Abdel-Aziz, Alaa A. -M. ;
Abdel-Aziz, Naglaa I. ;
El-Sayed, Magda A. -A. ;
Aleisa, Abdulaziz M. ;
Sayed-Ahmed, Mohamed M. ;
Abdel-Hamide, Sami G. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (09) :4188-4198
[9]   Discovery of alogliptin: A potent, selective, bioavailable, and efficacious inhibitor of dipeptidyl peptidase IV [J].
Feng, Jun ;
Zhang, Zhiyuan ;
Wallace, Michael B. ;
Stafford, Jeffrey A. ;
Kaldor, Stephen W. ;
Kassel, Daniel B. ;
Navre, Marc ;
Shi, Lihong ;
Skene, Robert J. ;
Asakawa, Tomoko ;
Takeuchi, Koji ;
Xu, Rongda ;
Webb, David R. ;
Gwaltney, Stephen L., II .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (10) :2297-2300
[10]   Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase (PARP) [J].
Griffin, RJ ;
Srinivasan, S ;
Bowman, K ;
Calvert, AH ;
Curtin, NJ ;
Newell, DR ;
Pemberton, LC ;
Golding, BT .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (26) :5247-5256