Next Article in Journal
Synthesis of (4-chlorobenzylidene)-(2-chloropyridi-3-yl)amine
Previous Article in Journal
Synthesis of N-(2-hydroxy-3-methoxybenzylidene) - 2, 3, 4, 6-tetra-O-acetyl -β-D galactopyranosylamine as a new chiral Schiff base for asymmetric [2+2] cycloadditions
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2005
Issue 4
10.3390/M437
molbank-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

Synthesis of 3,3´-[methylenebis(3,1-phenylenenitrilo)]bis[1,3-dihydro]-2H-indol-2-one as a novel bis-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(4), M437; https://doi.org/10.3390/M437
Submission received: 2 June 2005 / Accepted: 22 September 2005 / Published: 1 October 2005
Versions Notes

Isatin (1H-indole-2,3-dione) was first obtained by Erdman and Laurent in 1841 as a product from the oxidation of indigo by nitric and chromic acids [1]. The synthetic versatility of isatin has led to the extensive use of this compound in organic synthesis. In nature, isatin is found in plants of the genus Isatis [2], in Calanthe discolor LINDL [3]. Isatin is the biologically active chemical produced by an Altermones sp. Strain inhabiting the surface of embryos of the cardiean shrimp Palaemon macrodectylus, which protect them from the pathogenic fungus Lagenidium callinectes [4]. Schiff bases of isatin were reported to possess anti-HIV [5,6,7], anticonvulsant [8], antibacterial [9,10,11], antiprotozoal [12,13], antifungal [14,15,16], antiviral [17,18,19] and antihelminthic [20,21] activities. The Schiff bases of isatin have also been used as a ligand for complexation of metals such as copper (ІІ) [22]. Based on these facts, we decided to synthesize a new isatin bis-Schiff base as potential biological and complexometric agents. Its biological activities and analytical works are under study.
Molbank 2005 m437 i001
Isatin 1 (2.00 g, 13.6 mmol) and 3,3´-diaminodiphenylmethane 2 (1.35 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 17h and set aside. The resultant solidwas filtered and washed with ethanol. Pure Schiff base 3 was obtained upon recrystallization from ethanol (2.40 g, 77.3%).
Melting point: >260°C
IR(KBr, cm-1): 1652 (C=N); 1726.2 (C=O); 3168.8 (N-H).
1H-NMR (250MHz, DMSO-d6): δ= 10.96 (1H, s, N-H); 7.43-6.29 (16H, m, ArH); 4.07 (2H, s, CH2).
13C-NMR (62.9 MHz, DMSO-d6): δ= 72.54; 115.63; 116.39; 119.11; 120.04; 121.65; 122.25; 124.28; 126.41; 127.20; 130.18; 130.35; 134.66; 139.19; 147.51; 151.73; 155.53; 159.76; 168.29.
MS(m/z, %): 457 (17.40); 456 (34.40); 327 (12.40); 312 (31.40); 299 (14.20); 284 (23.40); 44 (100.00).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors are grateful to Shiraz University Research Council for financial support (Grant No.83-GR-SC-31 and 84-GR-SC-23 ).

References

  1. Dasilva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12(3), 273.
  2. Guo, Y.; Chen, F. Zhongcaoyao 1986, 17, 8, (CA 104:213068f).
  3. Yoshikawa, M.; Murakami, T.; Kishi, A.; Sakurama, T.; Matsuda, H.; Nomura, M.; Matsuda, H.; Kubo, M. Chem. Pharm. Bull. 1998, 46, 886. [PubMed]
  4. Gil-Turners, M. S.; Hay, M. E.; Fenical, W. Science 1989, 116.
  5. Pandeya, S. N.; Yogeeswari, P.; Sriram, D.; De Clercq, E.; Pannecouque, C.; Witvrouw, M. Chemotherapy 1999, 45, 192–196. [PubMed]
  6. Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Eur. J. Med. Chem. 2000, 35, 249–255. [PubMed]
  7. Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Arzneimittel Forschun./Drug Res. 2000, 50, 55–59.
  8. Sridhar, S. K.; Pandeya, S. N.; Stables, J. P.; Armes, S. K. Eur. J. Pharm. Sci. 2002, 16, 129. [PubMed]
  9. Pandeya, S. N.; Sriram, D. Acta Pharm. Turc. 1998, 40, 33.
  10. Sarangapani, M.; Reddy, V. M. Indian J. Pharm. Sci. 1994, 56, 174.
  11. Varma, R. S.; Nobles, W. L. J. J. Pharm. Sci. 1975, 64, 881. [PubMed]
  12. Imam, S. A.; Varma, R. S. Experientia 1975, 31, 1287. [PubMed]
  13. Varma, R. S.; Khan, I. A. Polish J. Pharmacol. Pharm. 1977, 29, 549.
  14. Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Indian J. Pharm. Sci. 1999, 61, 358.
  15. Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Sci.Pharm. 1999, 67, 103.
  16. Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Pharm. Acta Helv. 1999, 74, 11. [PubMed]
  17. Varma, R. S.; Nobles, W. L. J. Med. Chem. 1967, 10, 972. [PubMed]
  18. Singh, S. P.; Shukla, S. K.; Awasthi, L. P. Curr. Sci. 1983, 52, 766.
  19. Logan, J. C.; Fox, M. P.; Morgan, J. M.; Makohon, A. M.; Pfau, C. J. J. Gen. Virol. 1975, 28, 271. [PubMed]
  20. Sarciron, S. E.; Audin, P.; Delebre, I.; Gabrion, C.; Petavy, A. F.; Paris, J. J. Pharm. Sci. 1993, 82, 605. [PubMed]
  21. Et-savi, E. A.; Mostafa, T. B.; Mostafa, B. B. J. Egypt. Soc. Parasitol. 1998, 28, 481.
  22. Cerchiaro, G.; Micke, G. A.; Tavares, M. F. M.; Ferreira, A. M. D. C. J. Mol. Catal. A: Chem 2004, 221, 29.
  • Sample Availability: Available from MDPI.

Share and Cite

MDPI and ACS Style

Jarrahpour, A.A.; Khalili, D. Synthesis of 3,3´-[methylenebis(3,1-phenylenenitrilo)]bis[1,3-dihydro]-2H-indol-2-one as a novel bis-Schiff base. Molbank 2005, 2005, M437. https://doi.org/10.3390/M437

AMA Style

Jarrahpour AA, Khalili D. Synthesis of 3,3´-[methylenebis(3,1-phenylenenitrilo)]bis[1,3-dihydro]-2H-indol-2-one as a novel bis-Schiff base. Molbank. 2005; 2005(4):M437. https://doi.org/10.3390/M437

Chicago/Turabian Style

Jarrahpour, A. A., and D. Khalili. 2005. "Synthesis of 3,3´-[methylenebis(3,1-phenylenenitrilo)]bis[1,3-dihydro]-2H-indol-2-one as a novel bis-Schiff base" Molbank 2005, no. 4: M437. https://doi.org/10.3390/M437

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop