Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Antimicrobial Activity
3. Experimental
3.1. General
3.2. General Procedure for Preparation of E-l-Cyclopropyl-3-(p-substituted-phenyl)-2-propenenones 1a–c
3.3. General Procedure for Preparation of 1-Cyclopropyl-3-(p-substituted-phenyl)-2-propene-l-aroyl hydrazones 2a–e
3.4. General Procedure for Preparation of 1-Aroyl-3-cyclopropyl-5-(p-substituted-phenyl)-pyrazoles 3a–e
3.5. General Procedure for Preparation of 3-Acetyl-2-cyclopropyl-2-(p-substituted styryl)-5-(p-substituted phenyl)-1,3,4-oxadiazoles 4a–e
3.6. General Procedure for Preparation of 3-Cyclopropyl-5-(p-substituted Phenyl)isoxazole 5a–c
3.7. Determination of Antimicrobial Activity
4. Conclusions
References and Notes
- ABD El-Latif, N.A.; AMR Abd, E.-G.E.; Ibrahiem, A.A. Synthesis, reactions and pharmacological screening of heterocyclic derivatives using nicotinic acid as a natural synthon. Monatsh. Chem. 2007, 138, 559–567. [Google Scholar] [CrossRef]
- Gaede, B.J.; Mcdermott, L.L. Novel perfluoroalkyl-substituted pyrazoles. 1. hydroxypyrazoles. J. Heterocycl. Chem. 1993, 30, 49–54. [Google Scholar] [CrossRef]
- Shibata, K.; Katsuyama, I.; Izoe, H.; Matsui, M.; Muramatsu, H. Synthesis of 4,6-di substituted2-methyl pyridines and their 3-carboxamides. J. Heterocycl. Chem. 1993, 30, 277–281. [Google Scholar] [CrossRef]
- Jiaxi, X.; Wang, C.; Zhang, Q. Synthesis of 1-3,3a,5-tetraaryl-3a,4,5,6-tetrahydro3H-1,2,4-trizolo[4,3-a][1,5] benzodiazepines. Heteroatom Chem. 2001, 6, 557–559. [Google Scholar]
- Vibhute, Y.B.; Basser, M. A.Synthesis and activities of a new series of chalcones as anti bacterial agents. Indian J. Chem. 2003, 42B, 202–205. [Google Scholar]
- Bhat, B.A.; Dhar, K.L.; Saxena, A.K.; Shanmugavel, M. Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agent. Bioorg. Med. Chem. 2005, 15, 3177–3180. [Google Scholar] [CrossRef] [PubMed]
- Michael, L.E.; David, M.S.; Prasad, S.S. Chalcones: A new class of antimitotic agents. J. Med. Chem. 1990, 33, 1948–1954. [Google Scholar]
- Kalirajan, R.; Palanivelu, M.; Rajamanickam, V.; Vinothapooshan, G.; Andarajagopal, K. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. Int. J. Chem. Sci. 2007, 5, 73–78. [Google Scholar]
- Udupi, R.H.; Bhat, R.; Krishna, K. Synthesis and biological activity of Mannish bases of certain 1,2-pyrazolines. J. Heterocycl. Chem. 1998, 8, 143–146. [Google Scholar]
- Alka, P.; Saxena, V.K. Synthesis and antiviral activity of 4-(arylhydrazono)-3-methyl-1-(3,5-dinitrobenzoyl)-2-pyrazolin-5-ones. Indian J. Chem. 1987, 26B, 390–392. [Google Scholar]
- Urmila, G.; Vineeta, S.; Vineeta, K.; Sanjana, C. Synthesis and antifungal activity of new fluorine containing 4-(substituted phenylazo) pyrazoles and isoxazoles. Indian J. Heterocycl. Chem. 2005, 14, 265–266. [Google Scholar]
- Pandey, V.K.; Gupta, V.D.; Tiwari, D.N. Synthesis of substituted benzoxazines as potential antiviral agents. Indian J. Heterocycl. Chem. 2004, 13, 399–400. [Google Scholar]
- Clinton, R.O.; Manson, A.J.; Stonner, F.W.; Beyler, A.L.; Potts, G.O.; Arnold, A. Steroidal [3,2-c] pyrazoles. J. Am. Chem. Soc. 1959, 81, 1513–1514. [Google Scholar] [CrossRef]
- Kalirajan, R.; Sivakumar, S.U.; Jubie, S.; Gowramma, B.; Suresh, B. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. Int. J. Chem. Tech. Res. 2009, 1, 27–34. [Google Scholar]
- Azarifar, D.; Shaebanzadeh, M. Synthesis and characterization of new 3,5-dinaphthyl substituted 2-pyrazolines and study of their antimicrobial activity. Molecules 2002, 7, 885–895. [Google Scholar] [CrossRef]
- Mandge, S.; Singh, P.H.; Gupta, D.S.; Moorthy, N.H.S.N. Synthesis and characterization of some chalcone derivatives. Trends Appl. Sci. Res. 2007, 2, 52–56. [Google Scholar]
- Elba, M.E. Reductive debromination of erythro-2,3-dibromo-1-cyclopropyl-3-(p-substituted phenyl )-1-propanones. J. Pharm. Sci. 1995, 9, 43–46. [Google Scholar]
- Matter, U.E.; Pascual, C.; Pretsch, E.; Pross, A.; Simon, W.; Sternhell, S. Estimation of chemical shifts of olefinic protons using additive increments-II.The compilation of additive increments for 43 functional groups. Tetrahedron 1969, 25, 691–697. [Google Scholar] [CrossRef]
- Yale, H.L.; Losee, K.; Martins, J.; Holsing, M.; Perry, F.M.; Bernstein, J. Chemotherapy of experimental tuberculosis.VIII. The synthesis of acid hydrzides, their derivatives and related compounds. J. Am. Chem. Soc. 1953, 75, 1933–1942. [Google Scholar] [CrossRef]
- Faidallah, H.M.; Sharshira, E.M.; Basaif, S.A.; A-Ba-oum, A.E.-K. Synthesis and spectral characterization of novel 1,3,4-oxadiazole and 1,2,4-triazole derivatives: Synthesis for potential pharmacological activities. Phosphor. Sulfur Silicon Relat. Elem. 2002, 177, 67–79. [Google Scholar] [CrossRef]
- Schelz, Z.; Molnar, J.; Hohmann, J. Antimicrobial and antiplasmid activities of essential oils. Fitoterapia 2006, 77, 279–285. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Samples of all the compounds are available from the authors. |
Compound | X | Y | Yield (%) | Mp (ºC) | Molecular Formula | Calculated % | Found % | |||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
C | H | N | C | H | N | |||||||
2a | NO2 | Me | 72 | 181 | C20 H19 N3 O3 | 68.77 | 5.44 | 12.03 | 68.71 | 5.39 | 12.09 | |
2b | NO2 | NO2 | 79 | 201 | C19 H16 N4 O5 | 60.00 | 4.21 | 14.74 | 60.06 | 4.19 | 14.77 | |
2c | H | H | 66 | 166 | C19 H18 N2 O | 78.62 | 6.21 | 9.66 | 78.59 | 6.19 | 9.62 | |
2d | H | Me | 65 | 180 | C20 H20 O N2 | 78.95 | 6.58 | 9.21 | 79.01 | 6.49 | 9.28 | |
2e | OMe | Me | 69 | 190 | C21 H22 O2 N2 | 75.45 | 6.59 | 8.38 | 75.49 | 6.62 | 8.44 | |
2f | OMe | H | 74 | 160 | C20 H20 O2 N2 | 75.00 | 6.25 | 8.75 | 74.97 | 6.26 | 8.77 | |
3a | NO2 | Me | 81 | 183 | C20 H17 O3 N3 | 69.16 | 4.90 | 12.10 | 69.22 | 4.87 | 12.08 | |
3b | NO2 | NO2 | 92 | 197 | C19 H14 O5 N4 | 60.32 | 3.70 | 14.81 | 60.33 | 3.69 | 14.77 | |
3c | H | H | 62 | 159 | C19 H16 O N2 | 79.17 | 5.56 | 9.72 | 79.21 | 5.53 | 9.71 | |
3d | H | Me | 66 | 164 | C20 H18 O N2 | 79.47 | 5.96 | 9.27 | 79.51 | 5.91 | 9.27 | |
3e | OMe | Me | 64 | 171 | C21 H20 O2 N2 | 75.90 | 6.02 | 8.43 | 75.93 | 6.06 | 8.51 | |
3f | OMe | H | 59 | 180 | C20 H18 O2 N2 | 75.47 | 5.66 | 8.81 | 75.52 | 5.60 | 8.86 | |
4a | NO2 | Me | 83 | 201 | C22 H21 O4 N3 | 67.52 | 5.37 | 10.74 | 67.52 | 5.43 | 10.80 | |
4b | NO2 | NO2 | 97 | 210 | C21 H18 O6 N4 | 59.72 | 4.27 | 13.27 | 59.69 | 4.26 | 13.22 | |
4c | H | H | 59 | 177 | C21 H20 O2 N2 | 57.90 | 6.02 | 8.43 | 57.84 | 5.99 | 8.44 | |
4d | H | Me | 58 | 179 | C22 H22 O2 N2 | 76.30 | 6.36 | 8.09 | 76.28 | 6.31 | 8.12 | |
4e | OMe | Me | 67 | 189 | C23 H24 O3 N2 | 73.40 | 6.38 | 7.45 | 73.44 | 6.39 | 7.49 | |
4f | OMe | H | 80 | 162 | C22 H22 O3 N2 | 72.93 | 6.08 | 7.73 | 72.91 | 6.01 | 7.76 | |
5a | NO2 | ― | 54 | 165 | C12 H10 O3 N2 | 62.61 | 4.35 | 12.17 | 62.66 | 4.29 | 12.21 | |
5b | H | ― | 49 | 159 | C12 H11 O N | 77.84 | 5.95 | 7.57 | 77.90 | 5.99 | 7.62 | |
5c | OMe | ― | 74 | 161 | C13 H13 O2 N | 72.56 | 6.05 | 6.51 | 72.60 | 6.01 | 6.48 |
Compound | IR cm−1 (KBr) | 1H NMR (δ / ppm)a | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
C=C | C=N | C=O | NH | Ar–H’s and = C–CH=CH (m) | =C–CH=CH (d), J =12 Hz | Pyrazole-C4–H (s) or isoxazole–C4–H (s) | NH (s) | Cyclopropyl ring H’s | Ar–CH3 (s) Ar–OCH3 and CH3CO– | ||
CH (m) | 2 (CH2) (m) | ||||||||||
2a | 1592 | 1629 | 1678 | 3420 | 7.36–7.91 | 6.72 | ― | 10.66 | 1.91–2.55 | 0.75–1.37 | 2.21 |
2b | 1617 | 1647 | 1698 | 3390 | 7.23–8.45 | 6.93 | ― | 10.45 | 1.80–2.64 | 0.71–1.40 | ― |
2c | 1582 | 1616 | 1664 | 3330 | 7.19–7.63 | 6.60 | ― | 9.97 | 1.82–2.49 | 0.78–1.29 | ― |
2d | 1587 | 1636 | 1669 | 3336 | 7.29–7.82 | 6.71 | ― | 10.82 | 1.71–2.36 | 0.70–1.40 | 2.10 |
2e | 1601 | 1628 | 1687 | 3411 | 7.20–7.71 | 6.75 | ― | 10.73 | 1.63–2.40 | 0.77–1.46 | 2.19, 3.49 |
2f | 1617 | 1644 | 1681 | 3332 | 7.17–7.49 | 6.95 | ― | 9.99 | 1.56–2.59 | 0.78–1.16 | 3.42 |
3a | 1519 | 1629 | 1670 | ― | 7.26–7.92 b | ― | 6.85 | ― | 1.90–2.48 | 0.69–1.21 | 2.13 |
3b | 1586 | 1633 | 1684 | ― | 7.24–8.33 b | ― | 7.12 | ― | 1.76–2.66 | 0.80–1.36 | ― |
3c | 1556 | 1641 | 1660 | ― | 7.22–7.71 b | ― | 6.78 | ― | 1.73–2.40 | 0.71–1.28 | ― |
3d | 1590 | 1644 | 1678 | ― | 7.24–7.77 b | ― | 6.64 | ― | 1.75–2.41 | 0.77–1.33 | 2.11 |
3e | 1571 | 1623 | 1686 | ― | 7.21–7.68 b | ― | 6.69 | ― | 1.66–2.39 | 0.71–1.33 | 2.10,3.44 |
3f | 1596 | 1633 | 1664 | ― | 7.11–7.62 b | ― | 6.74 | ― | 1.49–2.55 | 0.77–1.19 | 3.39 |
4a | 1587 | 1645 | 1669 | ― | 7.18–7.79 b | ― | ― | ― | 1.92–2.41 | 0.67–1.32 | 2.01, 2.16 |
4b | 1610 | 1646 | 1667 | ― | 7.22–8.22 b | ― | ― | ― | 1.70–2.66 | 0.71–1.40 | 2.13 |
4c | 1602 | 1626 | 1669 | ― | 7.16–7.75 b | ― | ― | ― | 1.68–2.39 | 0.75–1.26 | 2.11 |
4d | 1594 | 1630 | 1670 | ― | 7.33–7.76 b | ― | ― | ― | 1.73–2.44 | 0.71–1.38 | 1.99, 2.13 |
4e | 1600 | 1633 | 1677 | ― | 7.26–7.72 b | ― | ― | ― | 1.60–2.47 | 0.71–1.26 | 2.13,3.32,2.15 |
4f | 1615 | 1646 | 1671 | ― | 7.25–7.51 b | ― | ― | ― | 1.47–2.61 | 0.76–1.33 | 3.34,2.10 |
5a | 1580 | 1627 | ― | ― | 7.19–7.99 b | ― | 5.69 | ― | 1.82–2.51 | 0.71–1.36 | ― |
5b | 1571 | 1629 | ― | ― | 7.22–7.62 b | ― | 5.42 | ― | 1.43–2.45 | 0.69–1.27 | ― |
5c | 1569 | 1633 | ― | ― | 7.26–7.70 b | ― | 5.46 | ― | 1.57–2.41 | 0.67–1.29 | 3.30 |
Compound | X | Y | Staphylococcus aureus | Escherichia coli |
---|---|---|---|---|
3a | NO2 | Me | + + + | + + + |
3b | NO2 | NO2 | + + + | + + + |
4a | NO2 | Me | + + + | + + + |
4b | NO2 | NO2 | + + + | + + + |
5a | NO2 | ― | + + + | + + + |
3e | OMe | Me | + + | + |
4c | H | H | + + | + |
4e | OMe | Me | + + | + |
4f 3c 3d 3f 4d 5b 5c | OMe H H OMe H H OMe | H H Me H Me ― ― | + + ― ― ― ― ― ― | + ― ― ― ― ― ― |
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Hamada, N.M.M.; Sharshira, E.M. Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives. Molecules 2011, 16, 2304-2312. https://doi.org/10.3390/molecules16032304
Hamada NMM, Sharshira EM. Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives. Molecules. 2011; 16(3):2304-2312. https://doi.org/10.3390/molecules16032304
Chicago/Turabian StyleHamada, Nagwa Mohamed Mahrous, and Essam Mohamed Sharshira. 2011. "Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives" Molecules 16, no. 3: 2304-2312. https://doi.org/10.3390/molecules16032304