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Molbank 2005, M429 |
Synthesis of 3-[(4-{3-[(2-oxo-1,2-dihydro-3H-indol-3-yliden)amino]phenoxy}phenyl)imino]-1H-indol-2-one as a
novel Schiff base
A. A. Jarrahpour*, D. Khalili
Department of
Chemistry,
Phone: 0098 711
2284822, Fax: 0098 711 2280926, e-mail: [email protected]
and [email protected]
Received:
Keywords: isatin, 3,4'-diaminodiphenyl ether, Schiff base, biological
activities
Isatin is an endogenous compound isolated in 1988 [1] and reported to possess a
wide range of central nervous system activities [2, 3]. Isatin
is the biologically active chemical produced by an alteromones
sp.strain inhabiting the surface of embryos of the cardiean shrimp palaemonmacrodectylus,
which protects them from the pathogenic fungus lagenidium
callinects [4]. Also isatin
is the major MAO B (endogenous monoamine oxidase)
inhibitory component of tribulin [5]. In some tissues
and body fluids, isatin does account for the MAO
B-inhibitory component, e.g. in cerebrospinal fluid. Schiff bases and Mannich bases of isatin were
reported to possess antibacterial [6-8], antifungal [9-11], antiviral [12-14],
anti HIV [15-17], antiprotozoal [18,19]. Another area of application of these Schiff bases is
analytical chemistry where some of these compounds are used as ligand in complexometry topic
[20]. In view of these facts we decided to synthesize a new Schiff base from isatin as potential biological and complexometric
agent. It¡¯s biological activities and analytical works
are under study.
Isatin 1 (2.00 g, 13.6 mmol)
and 3,4'-diaminodiphenyl ether 2 (1.36 g, 6.8 mmol) were dissolved in 35 mL of
warm ethanol containing 0.45 mL of acetic acid. The
reaction mixture was refluxed for 18 h and set aside. The resultant solid was
fitered and washed with ethanol. The pure Schiff base
3 was obtained upon recrystallization from
ethanol (1.93 g, 91.5%).
Melting point: >260 ¡ãC
IR (KBr, cm-1): 1620.0 (C=N); 1733.9 (C=O);
3028.0-3581.6 (N¨CH).
¹H-NMR (250MHz,
DMSO): ¦Ä= 6.16-7.77 (Ar-H, m, 16H); 10.94; 11.04 (N-H, s, 1H).
¹³C-NMR (62.9
MHz, DMSO: ¦Ä= 111.28; 111.98; 112.93; 115.97; 117.36;
118.60; 122.30; 122.76; 123.46; 124.29; 124.47; 125.98; 130.10; 131.26; 132.76;
132.88; 135.11; 135.60; 147.51; 153.49; 154.00; 155.42; 163.67; 192.86.
MS (m/z):
458,331, 330, 329, 302, 301, 286, 200, 194, 151, 150, 139, 133, 132, 128, 65,
54, 53, 52, 50, 44.
Acknowledgment
The authors
deeply thank the Shiraz University Research council for financial support(Grant No.83-GR-SC-31)
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