Abstract
2-[(3-Ethyl-4-oxo-3,4-dihydroquinazolin-2-yl)mercaptoacetylhydrazono]-3-alkyl/aralkyl-5-ethyl/propylthiazolidin-4-ones were synthesised by the cyclisation of 1-[(3-ethyl-4-oxo-3,4-dihydroquinazolin-2-yl)mercaptoacetyl]-4-alkyl/aralkyl thiosemicarbazides with ethyl 2-bromobutanoate or ethyl 2-bromopentanoate in the presence of anhydrous sodium acetate in anhydrous ethanolic medium. The regioisomer 2-alkyl/aralkyl 3-[(3-ethyl-4-oxo-3,4-dihydroquinazolin-2-yl)mercaptoacetylamino]-5-ethyl/propylthiazolidin-4-ones were not formed.
References
1.
Buckley
G.M.
,
Davies
N.
,
Dyke
H.J.
,
Gilbert
P.J.
,
Hannah
D.R.
,
Yaughan
A.F.
,
Hunt
C.A.
,
Pitt
W.R.
,
Profit
R.H.
,
Ray
N.C.
,
Richard
M.D.
,
Sharpe
A.
,
Taylor
A.J.
,
Whitworth
J.M.
, and
Williams
S.C.
, Bioorg. Med. Chem. Lett , 2005 , 15 , 751 .
2.
Schlapbach
A.
,
Heng
R.
, and
Padov
F.D.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 357 .
3.
Cushing
T.D.
,
He
X.
,
Smith
M.L.
,
Degraffenreid
M.R.
,
Powers
J.
,
Tomooka
C.S.
,
Clark
D.L.
,
Hao
X.
,
Jaen
J.C.
,
Labelle
M.
,
Walker
N.P.C.
,
Gill
A.L.
,
Talamas
F.X.
, and
Labadie
S.S.
, Patent WO 2003048152, Appl. WO 2002-US 39134, CAN 139:36536.
4.
Perrine
J.W.
,
Houlihan
W.J.
, and
Takesue
E.I.
, Arzneim. Forsch./Drug Res. , 1984 , 34 , 879 .
5.
Hour
M.J.
,
Huang
L.J.
,
Kuo
S.C.
,
Xia
Y.
,
Bastow
K.
,
Nakanishi
Y.
,
Hamel
E.
, and
Lee
K.H.
, J. Med. Chem. , 2000 , 43 , 4479 .
6.
Ashcroft
A.J.
,
Davies
F.E.
, and
Morgan
G.J.
, Lancet Oncol , 2003 , 4 , 284 .
7.
Marcelli
C.
,
Chappard
D.
,
Rossi
J.F.
,
Jaubert
J.
,
Alexandre
C.
,
Dessauw
P.
,
Baldet
P.
, and
Bataille
R.
, Cancer , 1988 , 62 , 1163 .
8.
Gürsoy
A.
, and
Ilhan
N.
, Il Farmaco , 1995 , 50 , 559 .
9.
Gürsoy
A.
, and
TerzioÐlu
N.
, Turk J Chem. , 2005 , 29 , 247 .
10.Sadtler , Research Laboratories, Inc. , Philadelphia , 1972 , 13248M .