Abstract
1,4-Phenylenediamine reacted readily with 2 mol of ethyl acetoacetate to give diethyl (2Z,2′Z)-3,3′-[(1,4-phenylene)-bisimino]dibut-2-enoate, which reacted with dimethylformamide dimethylacetal, activated methylene nitriles, ylidenemalononitriles and phenyl and benzoyl isothiocyanate to give, respectively, a 4,7-phenanthroline-2,9-dicarb-oxylate-1,10-diol, and tricyclic bispyridine and bispyrimidine derivatives. Two compounds showed strong antibacterial activity against several microorganisms, while six others showed high to moderate activity.
References
1.
Xie
L.
,
Tian
X.
, and
Li
G.
, PCT Int. Appl. , 2010 , WO 2010040275 A1 20100415.
2.
Peters
D.
,
Timmermann
D.B.
,
Olsen
G.M.
,
Nielsen
E.O.
,
Ahring
P.K.
,
Dyhring
T.
, and
Christensen
J.K.
, PCT Int. Appl. , 2010 , WO 2010026177 A1 20100311.
3.
Eun
J.S.
, and
Seo
S.-Y.
, Arch. Pharm. Res. , 2009 , 32 , 1673 .
4.
Kossen
K.
,
Seiwert
S.D.
,
Serebryany
V.
,
Ruhrmund
D.
,
Beigelman
L.
,
Raveglia
L.F.M.
,
Vallese
S.
,
Bianchi
I.
, and
Hu
T.
, PCT Int. Appl. , 2009 , WO 2009149188 A1 20091210.
5.
Li
S.
,
Guo
C.
,
Zhao
H.
,
Tang
Y.
, and
Lan
M.
, Bioorg. Med. Chem. , 2012 , 20 , 877 .
6.
Xu
G.
,
Abad
M.C.
,
Connolly
P.J.
,
Neeper
M.P.
,
Struble
G.T.
,
Springer
B.A.
,
Emanuel
S.L.
,
Pandey
N.
,
Gruninger
R.H.
,
Adams
M.
,
Moreno-Mazza
S.
,
Fuentes-Pesquera
A.R.
, and
Middleton
S.A.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 4615 .
7.
Xu
G.
,
Searle
L.L.
,
Hughes
T.V.
,
Beck
A.K.
,
Connolly
P.J.
,
Abad
M.C.
,
Neeper
M.P.
,
Struble
G.T.
,
Springer
B.A.
,
Emanuel
S.L.
,
Gruninger
R.H.
,
Pandey
N.
,
Adams
M.
,
Moreno-Mazza
S.
,
Fuentes-Pesquera
A.R.
,
Middleton
S.A.
, and
Greenberger
L.M.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 3495 .
8.
Antonios-McCrea
W.R.
,
Barsanti
P.A.
,
Hu
C.
,
Jin
X.
,
Martin
E.J.
,
Pan
Y.
,
Pfister
K.B.
,
Sendzik
M.
,
Sutton
J.
, and
Wan
L.
, PCT Int. Appl. , 2012 , WO 2012066070 A1 20120524.
9.
Brown
G.
,
Higginbottom
M.
,
Stewart
A.
,
Patient
L.
,
Carley
A.
,
Simpson
I.
,
Savory
E.D.
,
Oliver
K.
, and
Cole
A.G.
, PCT Int. Appl. , 2012 , WO 2012049277 A1 20120419.
10.
Wang
D.
,
Wang
B.
,
Zhu
H.
,
Zhu
X.
, and
Yu
J.
, Faming Zhuanli Shenqing , 2012 , CN 102321015 A 20120118.
11.
Antunes
A.M.M.
,
Sidarus
M.
,
Novais
D.A.
,
Harjivan
S.G.
,
Santos
P.P.
,
da Silva
J.L.F.
,
Beland
F.A.
, and
Marques
M.M.
, Molecules , 2012 , 17 , 2616 .
12.
Riggs-Sauthier
J.
, and
Deng
B.-L.
, PCT Int. Appl. 2011 , WO 2011103559 A1 20110825.
13.
Xie
L.
,
Tian
X.
, and
Li
G.
, Faming Zhuanli Shenqing , 2010 , CN 101717364 A 20100602.
14.
Miller
J.F.
,
Gudmundsson
K.S.
,
Richardson
L.D.
,
Jenkinson
S.
,
Spaltenstein
A.
,
Thomson
M.
, and
Wheelan
P.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 3026 .
15.
Mahalingam
A.K.
,
Axelsson
L.
,
Ekegren
J.K.
,
Wannberg
J.
,
Kihlstrom
J.
,
Unge
T.
,
Wallberg
H.
,
Samuelsson
B.
,
Larhed
M.
, and
Hallberg
A.
, J. Med. Chem. , 2010 , 53 , 607 .
16.
Nabih
I.
, and
Helmy
E.
, J. Pharm. Sci. , 1965 , 54 , 1698 .
17.
Elassar
A.-Z.A.
, J. Chem. Res. , 2012 , 36 , 328 .
18.
Al-Mousawi
S.M.
, and
Elassar
A.-Z.A.
, J. Heterocyl. Chem. , 2009 , 46 , 837 .
19.
Bangdiwala
B.P.
, and
Desai
C.M.
, J. Indian Chem. Soc. , 1954 , 31 , 688 .
20.
Giovanni
J.
, and
Nino
B.
, Gazzatta Chim. Ital. , 1939 , 69 , 111 .
21.
Backeberg
O.G.
, J. Chem. Soc. , 1935 , 1568 .
22.
Li
S.
,
Guo
C.
,
Zhao
H.
,
Tang
Y.
, and
Lan
M.
, Bioorg. Med. Chem. , 2012 , 20 , 877 .
23.
Gangjee
A.
,
Kurup
S.
,
Ihnat
M.A.
,
Thorpe
J.E.
, and
Shenoy
S.S.
, Bioorg. Med. Chem. , 2010 , 18 , 3575 .
24.
Hocková
D.
,
Holý
A.
,
Masojídková
M.
,
Andrei
G.
,
Snoeck
R.
,
De Clercq
E.
, and
Balzarini
J.
Bioorg. Med. Chem. , 2004 , 12 , 3197 .
25.
Watanabe
M.
,
Koike
H.
,
Ishiba
T.
,
Okada
T.
,
Seo
S.
, and
Hirai
K.
, Bioorg. Med. Chem. , 1997 , 5 , 437 .
26.
Gazivoda
T.
,
Raić-Malić
S.
,
Krištafor
V.
,
Makuc
D.
,
Plavec
J.
,
Bratulić
S.
,
Kraljević-Pavelić
S.
,
Pavelić
K.
,
Naesens
L.
,
Andrei
G.
,
Snoeck
R.
,
Balzarini
J.
, and
Mintas
M.
, Bioorg. Med. Chem. , 2008 , 16 , 5624 .
27.
Kers
I.
,
Macsari
I.
,
Csjernyik
G.
,
Nylöf
M.
,
Skogholm
K.
,
Sandberg
L.
,
Minidis
A.
,
Bueters
T.
,
Malmborg
J.
,
Eriksson
A.B.
,
Lund
P.-E.
,
Venyike
E.
,
Luo
L.
,
Nyström
J.-E.
, and
Besidski
Y.
, Bioorg. Med. Chem. Lett. , 2012 , 22 , 6108 .
28.
Krawczyk
S.
,
Otto
M.
,
Otto
A.
,
Coburger
C.
,
Krug
M.
,
Seifert
M.
,
Tell
V.
,
Molnár
J.
, and
Hilgeroth
A.
, Bioorg. Med. Chem. , 2011 , 19 , 6309 .