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Volume 2010
Issue 2
10.3390/M679
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Short Note

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

by
Abdullah M. 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), M679; https://doi.org/10.3390/M679
Submission received: 30 March 2010 / Accepted: 22 April 2010 / Published: 27 April 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-thienyl)prop-2-en-1-one (3) was synthesized in high yield by aldol condensation of 3-acetyl-2,5-dimethylthiophene 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 open-chain flavonoids with a common skeleton of 1,3-diaryl-2-propen-1-one [1]. They possess a wide range of biological activities such as antioxidant [2], antibacterial [3], antidepressant [4], antihypertensive [5] and anti-inflammatory activity [6]. Transformation of chalcones into pyrazoline derivatives can dramatically increase their biological properties such as antibacterial [7], antiprotozoal [8], or anti-inflammatory [9] activities. On the basis of these aspects we have synthesized a novel pyrazoline-based chalcone from 3-acetyl-2,5-dimethylthiophene and 3,5-dimethyl-1-phenylpyrazole-4-carboxaldehyde.
A solution of 3-acetyl-2,5-dimethylthiophene (0.38 g, 0.0025 mol) and 3,5-dimethyl-1-phenyl-pyrazole-4-carboxaldehyde (0.50 g, 0.0025 mol) in an ethanolic solution of NaOH (6.0 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, this solution was washed with a saturated solution of NaHCO3 and then evaporated to dryness. The residue was recrystallized from methanol/chloroform.
Light-yellow solid: yield: 78%; m.p. 111–112 °C.
EI-MS m/z (rel. int.%): 337 (65) [M+1]+,
IR (KBr) vmax cm–1: 3055 (Ar-H), 2918 (C-H), 1642 (C=O), 1575 (C=C).
1H NMR (DMSO-d6) (δ/ppm): 7.71 (d, 1H, J = 16.2 Hz, 8-CH), 7.35 (d, 1H, J = 16.0 Hz, 7-CH), 7.19 (s, 1H, thiophene 4-H), 7.24–6.93 (m, 5H, Ph), 2.65 (s, 3H, pyrazole 3-CH3), 2.44 (s, 3H, pyrazole 5-CH3), 2.37 (s, 3H, thiophene 2-CH3), 2.36 (s, 3H, thiophene 5-CH3).
13C NMR (150 MHz, CDCl3) δ: 185.43 (CO), 150.79 (10-C), 145.59, 140.04, 137.90, 136.00, 134.25, 133.86, 128.32, 127.74, 124.82, 123.89, 117.92, 114.32, 28.67, 14.92, 13.94, 11.96, 10.62.
Anal. calc. for C20H20N2OS: C, 71.40, H, 5.99, N, 8.33. Found: C, 71.36, H, 5.95, N, 8.28.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing the research facilities and the deanship of scientific research for the financial support of this work via Grant No. (3-045/430).

References and Notes

  1. 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]
  2. Bandgar, B.P.; Gawande, S.S. Synthesis and biological screening of a combinatorial library of β-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents. Bior. Med. Chem. 2010, 18, 2060–2065. [Google Scholar] [CrossRef] [PubMed]
  3. Nielsen, S.F.; Boesen, T.; Larsen, M.; Schonning, K.; Kromann, H. Antibacterial chalcones –bioisosteric replacement of the 4′-hydroxy group. Bioorg. Med. Chem. 2004, 12, 3047–3054. [Google Scholar] [CrossRef] [PubMed]
  4. Ozdemir, Z.; Kandilci, H.B.; Gumusel, B.; Calıs, U.; Bilgin, A.A. Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur. J. Med. Chem. 2007, 42, 373–379. [Google Scholar] [CrossRef] [PubMed]
  5. Ansari, F.L.; Iftikhar, F.; Ihsan-ul-Haq; Mirza, B.; Baseer, M.; Rashid, U. Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines. Bioorg. Med. Chem. 2008, 16, 7691–7697. [Google Scholar] [CrossRef] [PubMed]
  6. Asiri, A.M.; Khan, S.A. (2E,2'E)-3,3-(1,4-Phenylene)bis[1-(2,5-dimethyl-3-thienyl)prop-2-en-1-one]. Molbank 2009, 2009, M636. [Google Scholar] [CrossRef]
  7. 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] [PubMed]
  8. Chimenti, F.; Bizzarri, B.; Manna, F.; Bolasco, A.; Secci, D.; Chimenti, P.; Granese, A.; Rivanera, D.; Lilli, D.; Scaltrito, M.M.; Brenciaglia, M.I. Synthesis and in vitro selective anti-Helicobacter pylori activity of pyrazoline derivatives. Bioorg. Med. Chem. Lett. 2005, 15, 603–607. [Google Scholar] [CrossRef] [PubMed]
  9. Manna, F.; Chimenti, F.; Bolasco, A.; Cenicola, M.L.; Amico, M.D.; Parrillo, C.; Rossi, F.; Marmo, E. Anti-inflammatory, analgesic and antipyretic N-acetyl-Δ2-pyrazolines and dihydro-thienocoumarines. Eur. J. Med. Chem. 1992, 27, 633–639. [Google Scholar] [CrossRef]
Molbank 2010 m679 g001 550
Figure 1. Synthesis of compound 3.
Figure 1. Synthesis of compound 3.
Molbank 2010 m679 g001

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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-thienyl)prop-2-en-1-one. Molbank 2010, 2010, M679. https://doi.org/10.3390/M679

AMA Style

Asiri AM, Khan SA. (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-thienyl)prop-2-en-1-one. Molbank. 2010; 2010(2):M679. https://doi.org/10.3390/M679

Chicago/Turabian Style

Asiri, Abdullah M., and Salman A. Khan. 2010. "(2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-thienyl)prop-2-en-1-one" Molbank 2010, no. 2: M679. https://doi.org/10.3390/M679

APA Style

Asiri, A. M., & Khan, S. A. (2010). (2E)-3-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)-1-(2,5-dimethyl-3-thienyl)prop-2-en-1-one. Molbank, 2010(2), M679. https://doi.org/10.3390/M679

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