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Volume 2010
Issue 2
10.3390/M687
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Short Note

(2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one

by
Abdullah Mohamed Asiri
1,2,* and
Salman A. Khan
1
1
Chemistry Department, Faculty of Science, King Abdul Aziz University, P.O. Box 80203, Jeddah, Saudi Arabia
2
The Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, P.O. Box 80203, Saudi Arabia
*
Author to whom correspondence should be addressed.
Molbank 2010, 2010(2), M687; https://doi.org/10.3390/M687
Submission received: 8 May 2010 / Accepted: 27 May 2010 / Published: 8 June 2010
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Abstract

:
The title compound, (2E)-3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one (3) was synthesized in high yield by an aldol condensation between 3-acetyl-2,5-dimethylfuran and 3,5-dimethyl-1-phenylpyrazole-4-carboxaldehyde in ethanolic NaOH at room temperature. Its structure was fully characterized by elemental analysis, IR, 1H NMR, 13C NMR and EI-MS spectral analysis.

Graphical Abstract

Chalcones are also known as 1,3-diaryl-2-propen-1-ones, they belong to the flavonoid family. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system [1]. Chalcones have been reported to possess many useful properties, including anti-inflammatory [2], antimicrobial [3], antimitotic [4] antifungal [5], antioxidant [6] and anticancer activities [7]. Cyclization of chalcones such as pyrazoline can dramatically increase the biological activity such as antibacterial [8], antifungal [9], antiprotozoal [10], anti-inflammatory [11]. On the basis of these aspects, pyrazoline-containing chalcones should exhibit interesting biological activity. In this paper, we are reporting the synthesis of a novel pyrazoline-containing chalcone from 3-acetyl-2,5-dimethylfuran and 3,5-dimethyl-1-phenylpyrazole-4-carbox-aldehyde.
Molbank 2010 m687 g001 550
Figure 1. Synthesis of the title compound.
Figure 1. Synthesis of the title compound.
Molbank 2010 m687 g001
A solution of 3-acetyl-2,5-dimethylfuran (0.33 mL, 0.0025 mol) and 3,5-dimethyl-1-phenyl-pyrazole-4-carboxaldehyde (0.50 g, 0.0025 mol) in an ethanolic solution of NaOH (6 g in 10 mL of ethanol) was stirred for 16 h at room temperature. The solution was poured into ice-cold water of pH~2 (pH adjusted by HCl). The solid was separated and dissolved in CH2Cl2, washed with a saturated solution of NaHCO3 and evaporated to dryness. The residue was recrystallized from methanol/chloroform to give a light-yellow solid.
Yield: 75%; m.p. 109–110 °C
ESI-MS m/z (rel. int.%): 321 (72) [M+1]+
IR (KBr) vmax cm-1: 3043 (C-Haromatic), 2926 (C-Haliphatic), 1636 (C=O), 1562 (C=C).
1H NMR (600 MHz, CDCl3) (δ/ppm): 7.79 (d, 1H, C7, C=CH, J = 15.6 Hz,), 6.93 (d, 1H, C8, CO=CH, J = 15.6 Hz), 7.27 (s, 1H, C3, CH, furan), 7.49–6.90 (m, 5H, Ar-H), 2.63 (s, C2, CH3), 2.51 (s, C5, CH3), 2.43 (s, C10, CH3), 2.22 (s, C11, CH3).
13CNMR (150 MHz, CDCl3) δ: 185.99, 157.43, 149.92, 149.21, 141.08, 138.92, 134.11, 129.24, 128.18, 125.17, 124.28, 122.67, 121.08, 115.25, 114.32, 105.24, 14.51, 14.29, 13.28, 11.60.
Anal. calc. for C20H20N2O2: C, 78.98, H, 6.29, N, 8.74; Found: C, 78.93, H, 6.21, N, 8.72.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors would like to thank the deanship of scientific research for the financial support of this work via Grant No. (3-045/430).

References

  1. Nowakowska, Z. A review of anti-infective and anti-inflammatory chalcones. Eur. J. Med Chem. 2007, 42, 125–137. [Google Scholar] [CrossRef] [PubMed]
  2. Avila, H.P.; Smania, E.F.A.; Monache, F.D.; Smania, A., Jr. Structure–activity relationship of antibacterial chalcones. Bioorg. Med. Chem. 2008, 16, 9790–9794. [Google Scholar] [CrossRef] [PubMed]
  3. Batovska, D.; Parushev, S.; Stamboliyska, B.; Tsvetkova, I.; Ninova, M.; Najdenski, H. Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted. Eur. J. Med. Chem. 2009, 44, 2211–2218. [Google Scholar] [CrossRef] [PubMed]
  4. Ducki, S.; Forrest, R.; Hadfield, J.A.; Kendall, A.; Lawrence, N.J.; McGown, A.T.; Rennison, D. Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg. Med. Chem. Lett. 1998, 8, 1051–1056. [Google Scholar] [CrossRef]
  5. Lahtchev, K.L.; Batovska, D.I.; Parushev, S.P.; Ubiyvovk, V.M.; Sibirny, A.A. Antifungal activity of chalcones: A mechanistic study using various yeast strains. Eur. J. Med. Chem. 2008, 43, 2220–2228. [Google Scholar] [CrossRef] [PubMed]
  6. Detsi, A.; Majdalani, M.; Kontogiorgis, C.A.; Hadjipavlou-Litina, D.; Kefalas, P. Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity. Bioorg. Med. Chem. 2009, 17, 8073–8085. [Google Scholar] [CrossRef] [PubMed]
  7. Bandgar, B.P.; Gawande, S.S.; Bodade, R.G.; Totre, J.V.; Khobragade, C.N. Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Bioorg. Med. Chem. 2010, 18, 1364–1370. [Google Scholar] [CrossRef] [PubMed]
  8. Holla, B.S.; Akberali, P.M.; Shivananda, M.K. Studies on arylfuran derivatives: Part X. Synthesis and antibacterial properties of arylfuryl-Δ2-pyrazolines. Il Farmaco 2000, 55, 256–263. [Google Scholar] [CrossRef]
  9. Dawane, B.S.; Konda, S.G.; Mandawad, G.G.; Shaikh, B.M. Poly(ethylene glycol) (PEG-400) as an alternative reaction solvent for the synthesis of some new 1-(4-(4′-chlorophenyl)-2-thiazolyl)-3-aryl-5-(2-butyl-4-chloro-1H-imidazol-5yl)-2-pyrazolines and their in vitro antimicrobial evaluation. Eur. J. Med. Chem. 2010, 45, 387–392. [Google Scholar] [CrossRef] [PubMed]
  10. Budakoti, A.; Bhat, A.R.; Athar, F.; Azam, A. Syntheses and evaluation of 3-(3-bromo phenyl)-5-phenyl-1-(thiazolo [4,5-b] quinoxaline-2-yl)-2-pyrazoline derivatives. Eur. J. Med. Chem. 2008, 43, 1749–1757. [Google Scholar] [CrossRef] [PubMed]
  11. Khode, S.; Maddi, V.; Aragade, P.; Palkar, M.; Ronad, P.K.; Mamledesai, S.; Thippeswamy, A.H.M.; Satyanarayana, D. Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents. Eur. J. Med. Chem. 2009, 44, 1682–1688. [Google Scholar] [CrossRef] [PubMed]

Share and Cite

MDPI and ACS Style

Asiri, A.M.; Khan, S.A. (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one. Molbank 2010, 2010, M687. https://doi.org/10.3390/M687

AMA Style

Asiri AM, Khan SA. (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one. Molbank. 2010; 2010(2):M687. https://doi.org/10.3390/M687

Chicago/Turabian Style

Asiri, Abdullah Mohamed, and Salman A. Khan. 2010. "(2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-furanyl)prop-2-en-1-one" Molbank 2010, no. 2: M687. https://doi.org/10.3390/M687

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