Synthesis and biological activities of novel dialkyl (4-trifluoromethylphenylamino)-(4-trifluoromethyl or 3-fluorophenyl) methylphosphonates

被引:26
作者
Zhang, GP [1 ]
Song, B [1 ]
Xue, W [1 ]
Jin, LH [1 ]
Hu, DY [1 ]
Wan, QQ [1 ]
Lu, P [1 ]
Wang, H [1 ]
Yang, S [1 ]
Li, QZ [1 ]
Liu, G [1 ]
机构
[1] Guizhou Univ, Minist Educ Res & Dev, Ctr Fine Chem, Key Lab Green Pesticide & Agr Bioengn, Guiyang 550025, Peoples R China
基金
中国国家自然科学基金;
关键词
aminoalkylphosphonates; 4-trifluoromethylphenyl; 3-fluorophenyl; synthesis; anticancer activity; anti-TMV activity; microwave irradiation;
D O I
10.1016/j.jfluchem.2005.09.014
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of novel dialkyl (4-trifluoromethylphenylamino)-(4-trifluoromethyl or 3-fluorophenyl) methylphosphonates 3 were synthesized through the reaction of 3-fluorobenzaldehyde or 4-trifluoromethylbenzaldehyde and 4-trifluoromethylaniline with dialkyl phosphite by microwave irradiation using boron trifluoride-ether catalyst and their structures were clearly verified by spectroscopic data (IR, H-1 NMR and elemental analysis). The results of bioassay showed that these title compounds possess potential anticancer activities in vitro by MTT method. At the same time, we found these title compounds exhibit moderate antiviral activity against tobacco mosaic virus. (C) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:48 / 53
页数:6
相关论文
共 29 条
[11]   Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerase-targeted anticancer agents [J].
Gamage, SA ;
Spicer, JA ;
Rewcastle, GW ;
Milton, J ;
Sohal, S ;
Dangerfield, W ;
Mistry, P ;
Vicker, N ;
Charlton, PA ;
Denny, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :740-743
[12]  
GREGORY TP, 1998, PESTIC BIOCH PHYS, V60, P177
[13]   Synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones [J].
Jung, JC ;
Watkins, EB ;
Avery, MA .
TETRAHEDRON, 2002, 58 (18) :3639-3646
[14]   Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions [J].
Kaboudin, B ;
Nazari, R .
TETRAHEDRON LETTERS, 2001, 42 (46) :8211-8213
[15]   New potent antihyperglycemic agents in db/db mice: Synthesis and structure-activity relationship studies of (4-substituted benzyl)(trifluoromethyl)pyrazoles and -pyrazolones [J].
Kees, KL ;
Fitzgerald, JJ ;
Steiner, KE ;
Mattes, JF ;
Mihan, B ;
Tosi, T ;
Mondoro, D ;
McCaleb, ML .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (20) :3920-3928
[16]  
Küçükgüzel SG, 2000, EUR J MED CHEM, V35, P761
[17]   SYNTHESIS AND C-13 NMR OF (TRIFLUOROMETHYL)HYDROXYPYRAZOLES [J].
LEE, LF ;
SCHLEPPNIK, FM ;
SCHNEIDER, RW ;
CAMPBELL, DH .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (02) :243-245
[18]   SYNTHESIS, PHYSICAL AND BIOLOGICAL PROPERTIES OF THE PHOSPHORUS ANALOGS OF PHENYLALANINE AND RELATED-COMPOUNDS [J].
MAIER, L ;
DIEL, PJ .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 90 (1-4) :259-279
[19]   ORGANIC PHOSPHORUS-COMPOUNDS .94. PREPARATION, PHYSICAL AND BIOLOGICAL PROPERTIES OF AMINO-ARYLMETHYLPHOSPHONICACIDS AND AMINO-ARYLMETHYLPHOSPHONOUS ACIDS [J].
MAIER, L ;
DIEL, PJ .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 57 (1-2) :57-64
[20]   ESTERS CONTAINING PHOSPHORUS .1. [J].
MCCOMBIE, H ;
SAUNDERS, BC ;
STACEY, GJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1945, (MAY) :380-382