Abstract
Ethyl 2-[(2-amino-3-cyano-4-phenethyl-4H-naphtho[1,2-b]pyran-8-yl)oxy]acetate has been synthesised by condensation of ethyl 2-chloroacetate with the hydroxy group of 2-amino-8-hydroxy-4-phenethyl-4H-naphtho[1,2-b]pyran-3-carbonitrile. The latter was prepared from cinnamaldehyde, malononitrile and naphthalene-1,6-diol through Knoevenagel condensation and cyclisation reaction and then reduction with hydrogen in the presence of Pd/C at room temperature. The crystal structure of the title compound was determined. In addition, the compound showed distinct inhibition of the proliferation of some cancer cell lines.
References
1.
Costa M.
,
Dias T.A.
,
Brito A.
, and
Proenca F.
, Euro. J. Med. Chem. , 2016 , 123 , 487 .
2.
Kalla R.M.
,
Choi J.S.
,
Yoo J.W.
,
Byeon S.J.
,
Heo M.S.
, and
Kim I.
, Euro. J. Med. Chem. , 2014 , 76 , 61 .
3.
Alvey L.
,
Prado S.
,
Saint-Joanis B.
,
Michel S.
,
Koch M.
,
Cole S.T.
,
Tillequin F.
, and
Janin Y.L.
, Euro. J. Med. Chem. , 2009 , 44 , 2497 .
4.
Alvey L.
,
Prado S.
,
Huteau V.
,
Saint-Joanis B.
,
Michel S.
,
Koch M.
,
Cole S.T.
,
Tillequin F.
, and
Janin Y.L.
, Bioorg. Med. Chem. , 2008 , 16 , 8264 .
5.
Narender T.
,
Shweta S.
, and
Gupta S.
, Bioorg. Med. Chem. Lett. , 2009 , 14 , 3913 .
6.
Tandon V.K.
,
Vaish M.
,
Jain S.
,
Bhakuni D.S.
, and
Srimal R.C.
, Indian J. Pharm. Sci. , 1991 , 53 , 22 .
7.
Longobardi M.
,
Bargagna A.
,
Mariani E.
,
Schenone P.
, and
Marmo E.
, Il Farmaco , 1990 , 45 , 399 .
8.
Bargagna A.
,
Longobardi M.
,
Mariani E.
,
Schenone P.
, and
Falzarano C.
, Il Farmaco , 1992 , 47 , 345 .
9.
Gorlitzer K.
,
Dehre A.
, and
Engler E.
, Arch. Pharm. Weinheim Ger. , 1984 , 317 , 526 .
10.
Jiufu L.
,
Lingxia J.
,
Hongguang G.
,
Xiaohui J.
,
Xiaohua G.
,
Guanghui T.
,
Juan S.
, and
Min J.
, Chin. J. Struct. Chem. , 2017 , 36 , 1810 .
11.
Ermili A.
,
Roma G.
,
Buonamici M.
,
Cuttica A.
, and
Galante M.
, Il Farmaco , 1979 , 34 , 535 .
12.
Smith W.P.
,
Sollis L.S.
,
Howes D.P.
,
Cherry C.P.
,
Starkey D.I.
, and
Cobley N.K.
, J. Med. Chem. , 1998 , 41 , 787 .
13.
Hiramoto K.
,
Nasuhara A.
,
Michiloshi K.
,
Kato T.
, and
Kikugawa K.
, Mutat. Res. , 1997 , 395 , 47 .
14.
Martinez A.G.
, and
Marco L.J.
, Bioorg. Med. Chem. Lett. , 1997 , 7 , 3165 .
15.
Ju L.
,
Hongguang G.
, and
Jiufu L.
, J. Chem. Res. , 2015 , 39 , 4 .
16.
Ju L.
,
Xinwei Z.
,
Duanzheng S.
,
Zhiqiang C.
, and
Yunpeng Z.
, J. Chem. Res. , 2016 , 40 , 92 .
17.
Chhanda M.
, and
Arup D.
, Synth. Commun. , 2008 , 38 , 2103 .
18.
Sheldrick G.M.
, SHELXS 97, program for the solution of crystal structure. University of Göttingen , Göttingen , 1997 .
19.
Sheldrick G.M.
, SHELXL 97, program for the refinement of crystal structure. University of Göttingen , Göttingen , 1997 .
