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

doi:10.3390/M447

Department of Chemistry, College of Science, King Faisal University, P. O. Box 1759 Hofuf 31982, Saudi Arabia

Molbank2005, 2005(6), M447;https://doi.org/10.3390/M447

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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 [1,2,3,4,5]. Synthesis and study of the biological activity of isoindoline derivatives are under investigation.

To a stirred solution of o-phthalicaldehyde (1) (0.5 g, 3.73 mmol) 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°C.

UV (EtOH; λ_max nm; ε (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%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The author thanks Professor A. H. Moubasher and Professor A. Y. Abdel-Malek, Department of Botany, Assiut University, Assiut, Egypt, for the Biological Activity studies.

References

Takahashi, I.; Hatanaka, M. Heterocycles 1997, 45, 2475.
Kundu, N. G.; Khan, M. W.; Mukhopadhyay, R. Indian Chem. Soc. 2001, 78, 671.
Olmo, E.; Armas, M.; Ybarra, M.; López, J.; Oporto, P.; Giménez, A.; Deharo, E.; Feliciano, A. Bioorganic & Medicinal Chemistry Letters 2003, 13, 2769.
Takahashi, I.; Miyamoto, R.; Nishiuchi, K.; Hatanaka, M.; Yamano, A.; Sakushima, A.; Sakushima, A.; Hosoi, S. Heterocycles 2004, 63, 1267.
Cul, A.; Daïch, A.; Decroix, B.; Sanz, G.; Hijfte, L. Tetrahedron 2004, 60, 11029.

Sample Availability: Available from MDPI.

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