Abstract
The title compound, 5-(4-fluorophenyl)-N,N-dimethyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide, has been synthesised by condensation of dimethylamine with 5-(4-fluorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid. This intermediate was prepared from ethyl 5-amino-1H-pyrazole-4-carboxylate by cyclisation with 4,4,4-trifluoro-1-(4-fluorophenyl)butane-1,3-dione and then saponification with sodium hydroxide. The crystal structure of the title compound was determined. The compound possesses distinct effective inhibition on the proliferation of some cancer cell lines.
References
1.
Quiroga J.
,
Portilla J.
,
Abonía R.
,
Insuasty B.
,
Nogueras M.
, and
Cobo J.
, Tetrahedron Lett. , 2008 , 49 , 6254 .
2.
Ahmed O.M.
,
Mohamed M. A.
,
Ahmed R. R.
, and
Ahmed S. A.
, Eur. J. Med. Chem. , 2009 , 44 , 3519 .
3.
Williamson D.S.
,
Parratt M. J.
,
Bower J. F.
,
Moore J. D.
,
Richardson C. M.
,
Dokurno P.
, and
Jackson P. S.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 863 .
4.
Dwyer M.P.
,
Paruch K.
,
Labroli M.
,
Alvarez C.
,
Keertikar K. M.
,
Poker C.
, and
Parry D.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 467 .
5.
Gouda M.A.
,
Berghot M. A.
,
El-Ghani G. E. A.
, and
Khalil A. M.
, Eur. J. Med. Chem. , 2010 , 45 , 1338 .
6.
Tomcufcik A.S.
,
Albright J. D.
, and
Dusza J. P.
, US Patent 4,654,347, 1987 ; Chem. Abstr. , 1985, 107 , 220889m.
7.
Dusza J.P.
,
Albright J. D.
, and
Tomcufcik A. S.
, US Patent 5,538,977, 1996; Chem. Abstr. , 1996 , 125 , 168011c .
8.
Boes M.
,
Stadler H.
, and
Riemer C.
, US Patent 6,194,410, 2001; Chem. Abstr. , 1999 , 131 , 214304z .
9.
O'Donnell P.B.
, and
Thiele W. J.
, US Patent 6,384,221, 2002 ; Chem. Abstr. , 2001, 134 , 212744f.
10.
Fraley M.E.
,
Hoffman W. F.
,
Rubino R. S.
,
Hungate R. W.
,
Tebben A. J.
,
Rutledge R. Z.
,
McFall R. C.
,
Huckle W. R.
,
Kendall R. L.
,
Coll K. E.
, and
Thomas K. A.
, Bioorg. Med. Chem. Lett. , 2002 , 12 , 2767 .
11.
Ju L.
,
Hong-Guang G.
, and
Jiu-Fu L.
, J. Chem. Res. , 2015 , 39 , 4 .
12.
Ju L.
,
Xinwei Z.
,
Yang W.
,
Ye C.
,
Meirong Z.
,
Zhiqiang C.
, and
Lifeng X.
, Syn. Comm. , 2015 , 45 , 1009 .
13.
Katsuyama I.
,
Ogawa S.
,
Yamaguchi Y.
,
Funabiki K.
,
Matsui M.
,
Muramatsu H.
, and
Shibata K.
, Synthesis. , 1997 , 1321 .
14.
Sheldrick G.M.
, SHELXS-97, Program for the solution of crystal structures. University of Göttingen , Germany , 1997 .
