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Volume 2005
Issue 3
10.3390/M429
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Short Note

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

by
A. A. Jarrahpour
* and
D. Khalili
Department of Chemistry, College of Science, Shiraz University, Shiraz 71454, Iran
*
Author to whom correspondence should be addressed.
Molbank 2005, 2005(3), M429; https://doi.org/10.3390/M429
Submission received: 5 July 2004 / Accepted: 15 July 2004 / Published: 1 August 2005
Versions Notes

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 [6,7,8], antifungal [9,10,11], antiviral [12,13,14], anti HIV [15,16,17], 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.
Molbank 2005 m429 i001
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 °C
IR (KBr, cm-1): 1620.0 (C=N); 1733.9 (C=O); 3028.0-3581.6 (N–H).
¹H-NMR (250MHz, DMSO): δ= 6.16-7.77 (Ar-H, m, 16H); 10.94; 11.04 (N-H, s, 1H).
¹³C-NMR (62.9 MHz, DMSO: δ= 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.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors deeply thank the Shiraz University Research council for financial support(Grant No.83-GR-SC-31)

References

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  3. Bhattacharya, Salil K.; Mitra, Shankar K.; Acharya, Satya B. J. Psychopharmacol. 1991, 5, 202–206.
  4. Gil-Turners, M.S.; Hay, M.E.; Fenical, W. Science 1989, 246, 116–118.
  5. Medvedev, A.E.; Glover, V. NeuroToxicology 2004, 25, 185–192. [PubMed]
  6. Pandeya, S.N.; Sriram, D. Acta Pharm. Turc. 1998, 40, 33–38.
  7. Sarangapani, M.; Reddy, V.M. Indian J. Pharm. Sci. 1994, 56, 174–177.
  8. Varma, R.S.; Nobles, W.L. J. Pharm. Sci. 1975, 64, 881–882. [PubMed]
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  10. Pandeya, S.N.; Sriram, D.; Nath, G.; De Clercq, E. Sci. Pharm. 1999, 67, 103–111.
  11. Pandeya, S.N.; Sriram, D.; Nath, G.; De Clercq, E. Pharm.Acta Helv. 1999, 74, 11–17. [PubMed]
  12. Varma, R.S.; Nobles, W.L. J. Med. Chem. 1967, 10, 972–974. [PubMed]
  13. Singh, S.P.; Shukla, S.K.; Awasthi, L.P. Curr. Sci. 1983, 52, 766–769.
  14. Logan, J.C.; Fox, M.P.; Morgan, J.M.; Makohon, A.M.; Pfau, C.J. J. Gen. Virol. 1975, 28, 271–283. [PubMed]
  15. Pandeya, S.N.; Yogeeswari, P.; Sriram, D.; De Clercq, E.; Pannecouque, C.; Witvrouw, M. Chemotherapy 1999, 45, 192–196. [PubMed]
  16. Pandeya, S.N.; Sriram, D.; Nath, G.; De Clercq, E. Eur. J. Med. Chem. 2000, 35, 249–255. [PubMed]
  17. Pandeya, S.N.; Sriram, D.; Nath, G.; De Clercq, E. Arzneimittel Forschun,/Drug Res. 2000, 50, 55–59.
  18. Imam, S.A.; Varma, R.S. Experientia 1975, 31, 1287–1288. [PubMed]
  19. Varma, R.S.; Khan, I.A. Polish J. Pharmacol. Pharm. 1977, 29, 549–594.
  20. Rodriguez-Arguelles, M.C.; Belicchi Ferrari, M.; Bisceglie, F.; Pelizzi, C.; Pelosi, G.; Pinelli, S.; Sassi, M. J. Inorg. Biochem. 2004, 98, 313–321.
  • Sample Availability: Available from MDPI.

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MDPI and ACS Style

Jarrahpour, A.A.; Khalili, D. 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. Molbank 2005, 2005, M429. https://doi.org/10.3390/M429

AMA Style

Jarrahpour AA, Khalili D. 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. Molbank. 2005; 2005(3):M429. https://doi.org/10.3390/M429

Chicago/Turabian Style

Jarrahpour, A. A., and D. Khalili. 2005. "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" Molbank 2005, no. 3: M429. https://doi.org/10.3390/M429

APA Style

Jarrahpour, A. A., & Khalili, D. (2005). 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. Molbank, 2005(3), M429. https://doi.org/10.3390/M429

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