Molbank 2005, M447 |
Synthesis of antifungal isoindole (5-methyl-isoxazole-3-yl)-[2-(5-methyl-isoxazol-3-yl)2,3-dihydro-isoindol-1-ylidene]amine
Shar S. Al-Shihry
Department of Chemistry,
Tel. (+966)
35886435, Fax (+966) 35886437, e-mail:
[email protected]
Received:
Keywords: Isoindole, phthalimide, antifungal, Schiff base, isoxazole.
A large number of isoindoline skeletons such as staurosporine, indoprofen, and pazinaclone have been reported to possess biological activities
[1-5]. Synthesis and study of the biological activity of isoindoline
derivatives are under investigation.
To a
stirred solution of o-phthalicaldehyde (1) (0.5 g, 3.73mmol)
in dichloromethane (20 ml) a solution of amine 2 (0.73 g, 7.44 mmol) in dichloromethane
(20 ml) was added. The reaction mixture was heated under reflux for the 3h, the progress of the reaction was monitored by TLC. The
solvent was reduced and left, pale yellow cubic crystals start to form which
were filtered off to give the isoindole derivative 4 as colorless cubic crystals (0.75 g,
68 %).
Biological Activity: Compound 4 showed antifungal activity against
four species: Chrysoporium tropicum, Fusarium oxysporum, Geotrichum candidum and Trichoplyton rubrum.
Melting Point: 191¡ãC.
UV (EtOH; ¦Ëmax nm; ¦Å (dm3.mol-1.cm-1): 205 (10057); 242 (4583); 277 (4032).
IR (KBr,
cm-1): 3099 (CH);
1651 (C=N); 1430 (C-CH3); 1376 (C-N).
1H-NMR (CDCl3, 400 MHz): d= 7.49
(2H, d, J=7.5 Hz); 7.26-7.24 (2H, m); 7.11 (1H, s); 5.81 (1H, s); 4.96 (2H, s);
2.44 (3H, s); 2.39 (3H, s).
13C-NMR (CDCl3, 100 MHz): d=
170.3; 196.8; 166.8; 159.3; 155.6; 140.9; 132.0; 129.7; 127.9; 126.3; 123.3;
98.2; 96.2; 51.4; 13.0; 12.8.
MS (m/z, %): 294 (M+,
91.91); 279 (M+-CH3, 99.9); 117 (17.25); 116 (C8H4N,
100).
Elemental Analysis: Calculated for C16H14N4O2
(294.31): C, 65.30%; H, 4.79%; N, 19.04%. Found: C, 65.50%; H, 4.94%; N,
18.75%.
Acknowledgment
The author thanks Professor A. H. Moubasher and
Professor A. Y. Abdel-Malek, Department of Botany,
References
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3. Olmo, E.; Armas, M.; Ybarra, M.; L¨®pez, J.;
Oporto, P.; Gim¨¦nez, A.; Deharo, E.; Feliciano, A. Bioorganic & Medicinal
Chemistry Letters, 2003,
13, 2769.
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I.; Miyamoto, R.; Nishiuchi, K.; Hatanaka,
M.; Yamano, A.; Sakushima,
A.; Sakushima, A. Hosoi, S. Heterocycles, 2004, 63,
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5. Cul, A.; Daïch, A.; Decroix, B.; Sanz, G.; Hijfte, L. Tetrahedron,
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Sample Availability: Available from MDPI.
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