Abstract
The synthesis of new 4,5-substituted 1-[(2-hydroxyethoxy)methyl]-1,2,3-triazole 3a–e is described. The key step is the 1,3-dipolar cycloaddition between the azido group and an acetylenic group. Biological evaluation show significant activity.
References
1.
Schaeffer
H.J.
,
Beauchamp
L.
,
De Miranda
P.
, and
Elion
G.B.
, Nature (London) , 1978 , 272 , 583 .
2.
Tsilevich
T.L.
,
Shchaveleva
I.L.
,
Nosach
L.N.
,
Zhovnovataya
V.L.
,
Smirnov
I.P.
,
Kochetkova
S.V.
,
Gottikh
B.P.
, and
Florent'ev
V.L.
, J. Biol. Org. Chem. , 1988 , 14 , 379 –382 .
3.
Beauchamp
L.M.
,
Dolmatch
B.L.
,
Schaeffer
H.J.
,
Collins
P.
,
Bauer
D.J.
,
Keller
P.M.
, and
Fyfe
J.A.
, J. Med. Chem. , 1985 , 28 , 982 –987 .
4.
Lazrek
H.B.
,
Taourirte
M.
,
Oulih
T.
,
Kabbaj
Y.
,
Barrascut
J.L.
,
Imbach
J.L.
,
Almasoudi
N.A.
, and
Pfleiderer
W.
, Nucl. Nucl. , 1997 , 16 , 1073 –1077 .
5.
Lazrek
H.B.
,
Taourirte
M.
,
Oulih
T.
,
Lebtoumi
M.
,
Barrascut
J.L.
, and
Imbach
J.L.
, Nucl. Nucl. , 1997 , 16 , 1115 –1118 .
6.
Lazrek
H.B.
,
Engels
J.W.
, and
Pfleiderer
W.
, Nucl. Nucl. , 1998 , 17 , 1851 –1856 .
7.
Lazrek
H.B.
,
Rochdi
A.
, and
Engels
J.W.
, Nucl. Nucl. , 1999 , 18 , 1257 –1259 .
8.
Tanaka
H.
,
Fukui
M.
,
Hanaguchi
K.
,
Maskai
M.
, and
Miyasaka
T.
, Tetrahedron Lett. , 1989 , 30 , 2527 –2530 .
9.
Sallam
M.A.E.
, and
Townsend
L.B.
, Nucl. Nucl. , 1998 , 17 , 1215 –1229 .
10.
Sallam
M.A.E.
,
Louis
F.F.
, and
Cassady
J.M.
, Nucl. Nucl. , 1998 , 17 , 769 –783 .
11.
San-Felix
A.
,
Alvarez
R.
,
Velazquez
S.
,
De Clercq
E.
,
Balzarini
J.
, and
Camarasa
M.J.
, Nucl. Nucl. , 1995 , 14 , 595 –598 .
12.
Wigerinck
P.
,
Van Aerschot
A.
,
Claes
P.
,
Balzarini
J.
,
De Clercq
E.
, and
Herdewijn
P.
, J. Heterocyclic Chem. , 1989 , 26 , 1635 –1642 .
13.
Baker
J.J.
,
Mellish
P.
,
Riddle
C.
,
Somerville
A.R.
, and
Tittensor
J.R.
, J. Med. Chem. , 1974 , 17 , 764 –766 .
14.
Robinson
M.J.
, and
Hatfield
P.W.
, Can. J. Chem. , 1982 , 60 , 547 –553 .
15.
Barrio
J.R.
,
Bryant
J.D.
, and
Keyser
G.E.
, J. Med. Chem. , 1980 , 23 , 572 –574 .
16.
Lazrek
H.B.
,
Kaider
H.
,
Rochdi
A.
,
Barrascut
J.L.
, and
Imbach
J.L.
, Tetrahedron Lett. , 1996 , 37 , 4701 –4704 .
