Green Synthesis of α-Aminophosphonate Derivatives on a Solid Supported TiO2-SiO2 Catalyst and Their Anticancer Activity

被引:20
作者
Chinthaparthi, Radha Rani [1 ]
Bhatnagar, Ira [2 ]
Gangireddy, Chandra Sekhar Reddy [3 ]
Syama, Sundar Chereddy [1 ]
Cirandur, Suresh Reddy [1 ]
机构
[1] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India
[2] Ctr Cellular & Mol Biol, Lab Nanotechnol, Hyderabad 500007, Andhra Pradesh, India
[3] Sri Venkateswara Coll, Dept Chem, Tirupati, Andhra Pradesh, India
关键词
-Aminophosphonates; Anticancer activity; Green synthesis; HeLa and SK-BR-3 human cancer cells; TiO2-SiO2; ONE-POT SYNTHESIS; AMINO-PHOSPHONATES; 3-COMPONENT SYNTHESIS; EFFICIENT; DESIGN;
D O I
10.1002/ardp.201300214
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Syntheses of a new series of biologically potent -aminophosphonates were accomplished by one-pot Kabachnik-Fields reaction using TiO2-SiO2 as solid supported catalyst under microwave irradiation conditions. The chemical structures of all the newly synthesized compounds were confirmed by analytical and spectral (IR, H-1, C-13, P-31 NMR, and mass) data. Their anticancer nature was evaluated by screening the in vitro activity on two human cancer cell lines, HeLa and SK-BR-3. Compounds 4i and 4o showed the best activity on these cancer cells even though the majority of the compounds, and particularly 4l and 4p, have good cytotoxic activity against them.
引用
收藏
页码:667 / 676
页数:10
相关论文
共 45 条
[1]   Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates [J].
Abdel-Megeed, Mohamed F. ;
Badr, Badr E. ;
Azaam, Mohamed M. ;
El-Hiti, Gamal A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (07) :2252-2258
[2]  
Adriano C., 2010, TETRAHEDRON, V66, P7169
[3]   One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina [J].
Ambica ;
Kumar, Satish ;
Taneja, Subhash C. ;
Hundal, Maninder S. ;
Kapoor, Kamal K. .
TETRAHEDRON LETTERS, 2008, 49 (14) :2208-2212
[4]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[5]  
Arif D., 2012, GREEN CHEM, V14, P17
[6]   Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot [J].
Bhattacharya, Asish K. ;
Rana, Kalpeshkumar C. .
TETRAHEDRON LETTERS, 2008, 49 (16) :2598-2601
[7]   An efficient one-pot synthesis of α-amino phosphonates catalyzed by bismuth nitrate pentahydrate [J].
Bhattacharya, Asish K. ;
Kaur, Tanpreet .
SYNLETT, 2007, (05) :745-748
[8]  
Bing L., 2007, TETRAHEDRON, V63, P1981
[9]  
Chakrborti A. K., 2003, J CHEM SOC CHEM COMM, V39, P1896
[10]   Three component coupling catalyzed by TaCl5-SiO2:: synthesis of α-amino phosphonates [J].
Chandrasekhar, S ;
Prakash, SJ ;
Jagadeshwar, V ;
Narsihmulu, C .
TETRAHEDRON LETTERS, 2001, 42 (32) :5561-5563