Abstract
A cyanoacetohydrazide derivative underwent a series of reactions with different nucleophilic reagents, such as hydrazine hydrate, p-chlorobenzaldehyde and salicylaldehyde, to give the condensation products. In addition, an arylidene malononitrile was reacted with different nitrogen nucleophiles, such as hydrazine hydrate, thiocarbohydrazide and cyanoacetohydrazide, to afford the hydrazine, hydrazone and pyridin-2-one derivatives, respectively. Furthermore, a pyridin-2-one derivative was reacted with different carbon electrophiles, such as carbon disulfide, p-chlorobenzaldehyde and acetic anhydride. The antimicrobial activities of some of the compounds were examined.
References
1.
Pimerova E.V.
, and
Voronina E.V.
, J. Pharm. Chem. , 2001 , 35 , 18 .
2.
Janus S.L.
,
Magdif A.Z.
,
Erik B.P.
, and
Claus N.
, Monatsh Chem. , 1999 , 130 , 1167 .
3.
Bouabdallah I.
,
M'barek L.A.
,
Zyad A.
,
Ramadan A.
,
Zidane I.
, and
Melhaoui A.
, Nat. Prod. Res. , 2006 , 20 , 1024 .
4.
Park H.J.
,
Lee K.
,
Park S.
,
Ahn B.
,
Lee J.C.
,
Cho H.Y.
, and
Lee K.E.
, Bio Org. Med. Chem. Lett. , 2005 , 15 , 3307 .
5.
Yildirim I.
,
Ozdemir N.
,
Akçamur Y.
,
Dinçer M.
, and
Andaç O.
, Acta Cryst. , 2005 , E61 , 256 .
6.
Bailey D.M.
,
Hansen P.E.
,
Hlavac A.G.
,
Baizman E.R.
,
Pearl J.
,
Defelice A.F.
, and
Feigenson M.E.
, J. Med. Chem. , 1985 , 28 , 256 .
7.
Rovnyak G.C.
,
Millonig R.C.
,
Schwartz J.
, and
Shu V.
, J. Med. Chem. , 1982 , 25 , 1482 .
8.
Ozdemir Z.
,
Kandilici B.
,
Gumusel B.
,
Calis U.
, and
Bilgin A.
, Eur. J. Med. Chem. , 2007 , 42 , 373 .
9.
Ruhogluo O.
,
Ozdemir Z.
,
Calis U.
,
Gumusel B.
, and
Bilgin A.
, Arzneim. Forsch. , 2005 , 55 , 431 .
10.
Hees K.L.
,
Fitzgerald J.J.
,
Steiner K.E.
,
Mattes J.F.
,
Mihan B.
,
Tosi T.
,
Mondoro D.
, and
Mc Caleb M.L.
, J. Med. Chem. , 1996 , 39 , 3920 .
11.
Sener A.
,
Kasımoğulları R.
,
Sener M.K.
,
Bildirici I.
, and
Akcamur Y.
, J. Hetrocycl. Chem. , 2002 , 39 , 869 .
12.
Santilli A.A.
,
Kim D.H.
, and
Gregoy F.J.
, J. Pharm. Sci. , 1975 , 64 , 1057 .
13.
Chu C.K.
, and
Cutler J.
, J. Heterocycl. Chem. , 1986 , 23 , 289 .
14.
Rathelot P.
,
Azas N.
,
El-Kashef H.
,
Delmas F.
,
Giorgio C.D.
,
Timon-David P.
,
Maldonado J.
, and
Vanelle P.
, Eur. J. Med. Chem. , 2002 , 37 , 671 .
15.
Rahman A.U.
,
Choudhary M.I.
, and
Thomsen W.J.
, Bioassay techniques for drug development. Harwood Academic Publishers , Amsterdam , 2001 .
16.
Li J.-P.
,
Qiu J.-K.
,
Li H.-J.
, and
Zhang G.-S.
, J. Chin. Chem. Soc. , 2011 , 58 , 268 .