Abstract
A series of new dimethyl-3,6-di(aryl)-1,4-dihydro-1,2,4,5-tetrazine-1,4-dicarboxylates were synthesised through an intermolecular cyclisation reaction of methyl N'-(α-chloro-substituted benzylidene) hydrazinecarboxylate and triethylamine. Their 1,4-dihydro-s-tetrazine structures were characterised by IR, 1H NMR, MS, elemental analysis. Their antitumour activities were evaluated in vitro by the SRB method for A-549 cells and the MTT method for P-388 cells. The results show that none of the compounds had a high activity, but the substituents clearly had an effect on their antitumour activity.
References
1.
Saracoglu N.
, Tetrahedron , 2007 , 63 , 4199 .
2.
Haddadin M.J.
, and
Ghazvini-Zhadeh E.H.
, Tetrahedron Lett. , 2010 , 51 , 1654 .
3.
Neunhoeffer H.
, Comprehensive heterocyclic chemistry , ed.
Katritzky A.R.
Elsevier , Oxford , 1984 , Vol. 3 , pp. 531 –572 .
4.
Sauer J.
, Comprehensive heterocyclic chemistry , ed.
Boulton A.J.
Elsevier , Oxford , 1996 , Vol. 6 , pp. 901 –953 .
5.
Hu W.X.
,
Shi H.B.
,
Yuan Q.
, and
Sun Y.Q.
, J. Chem. Res. , 2005 , 91 .
6.
Hu W.X.
,
Rao G.W.
, and
Sun Y.Q.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 1177 .
7.
Hu W.X.
,
Sun Y.Q.
, and
Yuan Q.
, Chem. J. Chin. Univ. , 2002 , 23 , 1877 .
8.
Cai Z.B.
,
Zhou M.
,
Hu W.X.
, and
Yang Z.Y.
, Acta Pharmaceut. Sinica , 2000 , 35 , 793 .
9.
Rao G.W.
,
Guo Y.M.
, and
Hu W.X.
, Chem. Med. Chem. , 2012 , 7 , 973 .
10.
Rao G.W.
, and
Hu W.X.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 3702 .
11.
Lv L.P.
,
Yu W.P.
,
Yu W.B.
,
Zhou X.F.
, and
Hu X.C.
, Acta Crystallogr. E , 2008 , 64 , o1676 .
12.
Ito S.
,
Tanaka Y.
, and
Kakehi A.
, Bull. Chem. Soc. Jpn. , 1976 , 49 (3 ), 762 .
13.
Tullio B.
, Gaz. Chim. Ital. , 1961 , 91 , 866 .
14.
Golfier M.
,
Guillerez M.G.
, and
Milcent R.
, Tetrahedron Lett. , 1974 , 44 , 3875 .
15.
Rao G.W.
,
Wang C.
,
Wang J.
,
Zhao Z.G.
, and
Hu W.X.
, Bioorg. Med. Chem. Lett. , 2013 , 23 , 6474 .