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Short Note

Synthesis, Physical Characterization, Antibacterial and Antifungal activities of a novel bis(3-((E)-1-(2-hydroxyphenyl)ethylideneamino)phenyl)methanone

by
A. F. Jalbout
1,*,
A. A. Jarrahpour
2,*,
J. M. Brunel
3,
C. Salmi
3,
S. Rezaei
2 and
B. Trzaskowski
1
1
Department of Chemistry, the University of Arizona, Tucson, AZ 85721 USA
2
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
3
Laboratoire SESNAB, Faculté de St Jérôme, Case 342, Université Paul Cézanne, Av. Escadrille Normandie Niémen, 13397 Marseille cedex 20, France
*
Authors to whom correspondence should be addressed.
Molbank 2006, 2006(4), M484; https://doi.org/10.3390/M484
Submission received: 13 January 2006 / Accepted: 3 March 2006 / Published: 1 June 2006
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Abstract

:
Bis (3-((E)-1-(2-hydroxyphenyl) ethylideneamino) phenyl) methanone has been synthesized in this paper and its structure was confirmed by 1H-NMR, 13C-NMR, IR and Mass spectra. Its AM1 and B3LYP/6-31G* calculations to characterize the physical properties of this molecule has been also presented. Finally, the antifungal and antibacterial activities of this derivative have been evaluated.

Introduction

Particular attention has recently been paid to the synthesis and study of the diimino tetradentate Schiff bases and their complexes. This is due to their uses as biological models in understanding the structure of biomolecules and biological processes. The crucial role of Schiff bases in the biological function of bacteriorhodospin is proven. The retinal chromophore is bound covalently to the protein via a protonated Schiff base [1].Schiff-base ligands derived from 2-hydroxyacetophenone have been used as complexing agents [2]. In these ligands the electronic, steric and geometric effect of a methyl group on an imine carbon on asymmetric catalytic reactions can be investigated [3]. Salen type complexes are very well studied because this type of Schiff base ligands present suitable biometric properties that can mimic the structural feature of the active site[4].Based on these facts we decided to synthesize a new bis Schiff base derived from 2-hydroxyacetophenone.

Results and Discussion:

3,3'-Diaminobenzophenone 1 (0.212g, 1.00mmol) and 2-Hydroxyacetophenone 2 (0.272g, 2.00mmol) were dissolved in 10 mL of warm ethanol. The reaction mixture was refluxed for 10h and allowed to stand aside. The crystals were filtered off and washed with ethanol. The pure Schiff base 3 was recrystalized from ethanol as light yellow crystals. The IR spectrum showed the characteristic absorption of Schiff base C=N at 1612 cm-1. The 1H-NMR spectrum showed a multiplet for aromatic protons at 6.76-7.85 ppm. The OH group appeared as a singlet at 14.37 ppm. The 13C-NMR spectrum showed C=N group at 162.23, C=O group at 196.97 and the CH3 group at (18.48, 30.61). The mass spectrum showed the (M+1) peak at 449. The yield was 57%.
Melting point: 182-184 °C.
IR (KBr, cm-1): 3248; 1716; 1612 cm-1.
1H NMR (250 MHz, CDCl3): δ= 14.37 (OH); 7.85- 6.76 (Aromatic protons); 1.65 (s, CH3).
13C NMR (62.9 MHz, CDCl3): δ= 196.97; 162.23; 148.62; 138.29; 117.67; 116.98; 114.34; 30.61; 18.48.
MS: 449 (M+1), 195, 120, 92, 65, 43.
Molbank 2006 m484 i001
All calculations in this work where carried out with the AM1 level of theory using the GAUSSIAN 03 [5] suite of programs. In addition we have carried very intense B3LYP/6-31G* optimizations and frequency calculations. More information about these methods is available elsewhere [6]. Figure 1 presents the optimized structure of the molecule with bond lengths and bond angles shown as well as the theoretical IR vibrational spectrum.
Table 1 shows the thermodynamic properties for the where T (temperature in K), S (entropy in J mol-1 K-1), Cp (heat molecule in Figure 1 capacity at constant pressure in kJ mol-1 K-1), and ΔH=H° - H°298.15 (enthalpy content, in kJ mol-1), T1=100 K, T2=298.15 K, and T3=1000 K calculated AM1 and B3LYP/6-31G* frequencies. The fits were performed according to the equations implemented by the National Institute of Standards and Technology (NIST) [7]. These equations have been very good at predicting physical properties of various molecules, as we have tested in the past [6,7,8,9,10].

Antibacterial and antifungal tests

Derivative 3 was evaluated for its in vitro biological properties against human pathogens [11]. This compound was found to possess no antifungal activities against S. cerevisiae (ATCC 28383) and no antibacterial activities against Gram-positive and Gram-negative bacteria even if a slight antibacterial activity against S. aureus (CIP 4.83) at a concentration of 100 µg/mL has been noticed (Table 2).

Supplementary Materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

AFJ and BT would like to thank the University of Arizona supercomputer center for over 200 hours of computer time for these calculations. AAJ and SR thank the Shiraz University Research Council for financial support (Grant No.84-GR-SC-23)

References

  1. Boghaei, D.M.; Gharagozlou, M. Spectrochimica Acta Part A 61. 2005, 3061–3065. [Google Scholar] [PubMed]
  2. Zhang, J. X.; Zhou, Y.; Cai, G. J. J. Mol. Catal 1997, 11, 41–44.Holland, D.; Laidler, D.A.; Milner, D.J. J. Mol. Catal 1981, 11, 119–127.Chen, G. M.; Chen, F.; Zhou, C. Chem. Chin. Univ 1995, 16, 216–219.Qiu, M.; Liu, G.; Yiao, X. Chin. J.Catal 2001, 22, 77–80.Li, C.; Zhang, W.; Yao, X. Chin. J, Catal. 2000, 21, 77–80.Li, Z. N.; Liu, G.; Zheng, Z. Tetrahedron 2000, 56, 7187–7191.
  3. Gao, W. T.; Zheng, Z. Molecules 2002, 7, 511–516.
  4. Karmakar, R.; Choudhury, C. R.; Bravic, G.; Sutter, J. P.; Mitra, S. Polyhedron 2004, 23, 949–954.
  5. Frisch, M.J.; et al. GAUSSIAN 03, Revision A.1, M. J. Frisch, et. Al. Gaussian, Inc.: Pittsburgh PA, 2003. [Google Scholar]
  6. Foresman, J.B. Æ Frisch, , Exploring Chemistry with Electronic Structure Methods. In 2nd edition; Gaussian, INC: Pittsburgh, PA, 1996. [Google Scholar]
  7. Linstrom, P.J.; Mallard, W.G. (Eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. July 2001. National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov)
  8. Jalbout, A.F.; Solimannejad, M.; Labonowski, J.K. Chem. Phys. Lett. 2003, 379, 503.
  9. Jalbout, A.F.; Jiang, Z.-Y.; Quasri, A.; Jeghnou, H.; Rhandour, A.; Dhamelincourt, M.C.; Dhamelincourt, P.; Mazzah, A. Vib. Spect. 2003, 33, 21.
  10. Jalbout, A.F.; Nazara, F.; Turker, L. J. Mol. Struct. (THEOCHEM) 2004, 627, 1, (Invited Review).
  11. Growth was measured in vitro using a liquid-phase method according to NCCLS guidelines from the American Society of Microbiology for 24 hours using various concentrations of drugs. Dei Cas, E.; Dujardin, L.; Ribeiro Pinto, M. E.; Ajana, F.; Fruit, J.; Poulain, D.; Camus, D.; Vernes, A.; Francois, N. Mycoses 1991, 34, 167–172. [PubMed]
  • Sample Availability: Available from MDPI.
Molbank 2006 m484 g001 550
Figure 1. AM1 optimized structure and its theoretical IR vibrational spectrum for molecule 3.
Figure 1. AM1 optimized structure and its theoretical IR vibrational spectrum for molecule 3.
Molbank 2006 m484 g001
Table
Table 1. Thermodynamic properties of the molecule 3 in Figure 1, calculated at the AM1 level and B3LYP/6-31G* level of theory, where Cp is the heat capacity in J mol-1 K-1, S is the entropy in J mol-1 K-1, and ΔH is the standard enthalpy kJ mol-1. These where fitted to the Shomate equations which are implemented by the JANAF tables of the NIST databases. These equations converged to an R2 value of 0.999 on average.
Table 1. Thermodynamic properties of the molecule 3 in Figure 1, calculated at the AM1 level and B3LYP/6-31G* level of theory, where Cp is the heat capacity in J mol-1 K-1, S is the entropy in J mol-1 K-1, and ΔH is the standard enthalpy kJ mol-1. These where fitted to the Shomate equations which are implemented by the JANAF tables of the NIST databases. These equations converged to an R2 value of 0.999 on average.
Fitted Thermodynamic Equation (T/1000=t)100 K298.15 K1000 K
Cp 61.26809+ 1473.5495*t -123.39616*t2 -341.74085*t3 -0.0486*t-2205.78 477.77 1077.52
S53.05624*ln(t) + 1474.23257*t + 423.72982*t2/2 -484.29762*t3/3 -32.45372/(2*t2) -3357.13221518.49 863.88 1807.1
H89.57261*t + 1689.9106*t2/2 -308.96521*t3/3 -332.76221*t4/4 + 0.78161/t -370.05113.13 80.56 670.35
Table
Table 2. Antimicrobial activity of Schiff base 3.
Table 2. Antimicrobial activity of Schiff base 3.
Sample CIPAntimicrobial activity (MIC), µg/mL
S. cerevisiae (ATCC 28383)S. aureus (4.83)C. albicans (1180-79)E. Coli (54127)
3>100100>100>100

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MDPI and ACS Style

Jalbout, A.F.; Jarrahpour, A.A.; Brunel, J.M.; Salmi, C.; Rezaei, S.; Trzaskowski, B. Synthesis, Physical Characterization, Antibacterial and Antifungal activities of a novel bis(3-((E)-1-(2-hydroxyphenyl)ethylideneamino)phenyl)methanone. Molbank 2006, 2006, M484. https://doi.org/10.3390/M484

AMA Style

Jalbout AF, Jarrahpour AA, Brunel JM, Salmi C, Rezaei S, Trzaskowski B. Synthesis, Physical Characterization, Antibacterial and Antifungal activities of a novel bis(3-((E)-1-(2-hydroxyphenyl)ethylideneamino)phenyl)methanone. Molbank. 2006; 2006(4):M484. https://doi.org/10.3390/M484

Chicago/Turabian Style

Jalbout, A. F., A. A. Jarrahpour, J. M. Brunel, C. Salmi, S. Rezaei, and B. Trzaskowski. 2006. "Synthesis, Physical Characterization, Antibacterial and Antifungal activities of a novel bis(3-((E)-1-(2-hydroxyphenyl)ethylideneamino)phenyl)methanone" Molbank 2006, no. 4: M484. https://doi.org/10.3390/M484

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