Next Article in Journal
[5-(1,3-Diphenyl-1H-pyrazol-4-yl)-3-phenyl-4,5-dihydropyrazol-1-yl](pyridin-4-yl)methanone
Previous Article in Journal
Methyl 4-[(Benzoylamino)methoxy]benzoate
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

(2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone

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 2011, 2011(1), M713; https://doi.org/10.3390/M713
Submission received: 2 December 2010 / Accepted: 6 January 2011 / Published: 7 January 2011

Abstract

:
The title compound, (2E)-1-(2,5-dimethyl-3-thienyl)3-(4-nitrophenyl)propenone (3) was synthesized in high yield by reaction of 3-acetyl-2,5-dimethythiophene and 4-nitrobenzaldehyde in the presence of sodium hydroxide. The structure of the compound was fully characterized by IR, 1H NMR, 13C NMR, GC-MS spectral analysis and elemental analysis.

Graphical Abstract

1,3-Diaryl-2-propen-1-ones (chalcones) are products of condensation of simple or substituted aromatic aldehydes with simple or substituted acetophenones in the presence of alkali [1]. Chalcones constitute an important group of natural products and some of them possess a wide range of biological activities such as antimicrobial, anticancer, antitubercular, antiviral, etc. Recent studies on biological evaluation of chalcones revealed their potential to be antimalarial [2], antifungal [3], anticancer [4], antioxidant [5], tyrosinase inhibitory [6], anti-inflammatory [7] and antibacterial [8]. Some derivatives of chalcones are used as sweeteners, drugs, and sunscreen agents [9]. They are also well-known intermediates for the synthesis of various heterocyclic compounds such as pyrimidines, pyrazolines, pyrazoles, or thiazines [10]. These observations led us to synthesize a new chalcone from 3-acetyl-2,5-dimethythiophene and 4-nitrobenzaldehyde in analogy to a previous report [11].
Scheme 1. Synthesis of the title compound (3).
Scheme 1. Synthesis of the title compound (3).
Molbank 2011 m713 sch001
A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 0.0025 mol) and 4-nitrobenzaldehyde (0.37 g, 0.0025 mol) in an ethanolic solution of NaOH (3.0 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 which separated was filtered and crystallized from methanol/chloroform.
Light-yellow solid: yield: 78%; m.p. 130–131 °C.
GC-MS m/z (rel. int. %): 289 (62) [M+1]+.
IR (KBr) vmax cm−1: 3012 (Ar-H), 2926 (C-H), 1628 (C=O), 1568 (C=C).
1H NMR (600 MHz, DMSO-d6) (δ/ppm): 8.47 (d, J = 1.8 Hz), 8.23 (d, J = 1.2 Hz), 7.73 (d, C=CH, J = 15.6 Hz), 7.40 (d, CH=C, J = 15.6 Hz), 7.89 (d, J = 7.2 Hz), 7.61 (d, J = 7.8 Hz), 7.27 (s, Ar-H), 2.72 (s, CH3), 2.39 (s, CH3).
13CNMR (150 MHz, CDCl3) δ: 185.23, 148.66, 148.62, 140.32, 136.79, 136.01, 135.68, 134.31, 129.98, 127.45, 125.76, 124.43, 122.16, 16.06, 15.05.
Anal. calc. for C15H13NO3S: C, 62.70, H, 4.56, N, 4.87. Found: C, 62.66, H, 4.52, N, 4.83.

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. Asiri, A.M.; Khan, A.S. 1-(2,5-Dimethyl-3-thienyl)-3-(2,4,5-trimethyphenyl)prop-2-en-1-one. Molbank 2010, 2010, M692. [Google Scholar] [CrossRef]
  2. Bhattacharya, A.; Mishra, L.C.; Sharma, M.; Awasthi, S.K.; Bhasin, V.K. Antimalarial pharmacodynamics of chalcone derivatives in combination with artemisinin against Plasmodium falciparum in vitro. Eur. J. Med. Chem. 2009, 44, 3388–3393. [Google Scholar] [CrossRef] [PubMed]
  3. Lopez, S.N.; Castelli, M.V.; Zacchino, S.A.; Dominguez, J.N.; Lobo, G.; Charris-Charris, J.; Cortes, C.G.; Ribas, J.C.; Devia, C.; Rodriguez, A.M.; Enriz, R.D. In vitro antifungal evaluation and structure–activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall. Bioorg. Med. Chem. 2001, 9, 1999–2013. [Google Scholar] [CrossRef]
  4. Kamal, A.; Ramakrishna, G.; Raju, P.; Viswanath, A.; Ramaiah, M.J.; Balakishan, G.; Pal-Bhadra, M. Synthesis and anti-cancer activity of chalcone linked imidazolones. Bioorg. Med. Chem. Lett. 2010, 20, 4865–4869. [Google Scholar] [CrossRef] [PubMed]
  5. Hao, Z.N.; Wang, L.P.; Tao, R.X. Expression patterns of defence genes and antioxidant defence responses in a rice variety that is resistant to leaf blast but susceptible to neck blast. Physiol. Mol. Plant P. 2009, 74, 167–174. [Google Scholar] [CrossRef]
  6. Khatib, S.; Nerya, O.; Musa, R.; Shmuel, M.; Tamir, S.; Vaya, J. Chalcones as potent tyrosinase inhibitors: The importance of a 2,4-substituted resorcinol moiety. Bioorg. Med. Chem. 2005, 13, 433–441. [Google Scholar] [CrossRef] [PubMed]
  7. Tuchinda, P.; Reutrakul, V.; Claeson, P.; Pongprayoon, U.; Sematong, T.; Santisuk, T.; Walter, C.; Taylor, W.C. Anti-inflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata. Phytochemistry 2002, 59, 169–173. [Google Scholar] [CrossRef]
  8. Selvakumar, N.; Kumar, G.S.; Azhagan, A.M.; Rajulu, G.G.; Sharma, S.; Kumar, M.K.; Das, J.; Iqbal, J.; Trehan, S. Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids. Eur. J. Med. Chem. 2007, 42, 538–583. [Google Scholar] [CrossRef] [PubMed]
  9. Krohn, K.; Steingrover, K.; Rao, M.S. Isolation and synthesis of chalcones with different degrees of saturation. Phytochemisy 2002, 61, 931–936. [Google Scholar] [CrossRef]
  10. Sharma, M.; Chaturvedi, V.; Manju, Y.K.; Bhatnagar, S.; Srivastava, K.; Puri, S.K.; Chauhan, P.M.S. Substituted quinolinyl chalcones and quinolinyl pyrimidines as a new class of anti-infective agents. Eur. J. Med. Chem. 2009, 44, 2081–2091. [Google Scholar] [CrossRef] [PubMed]
  11. Hassan, M.A.; Batterjee, S.; Taib, L.A. Stereoselective crossed-aldol condensation of 3-acetyl-2,5-dimethylthiophene/furan with aromatic aldehydes in water: Synthesis of (2E)-3-aryl-1-(thien-3-yl/fur-3-yl)-prop-2-en-1-ones. Ind. J. Chem. B 2006, 45B, 1936–1941. [Google Scholar] [CrossRef]

Share and Cite

MDPI and ACS Style

Asiri, A.M.; Khan, S.A.; Khan, K.A. (2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone. Molbank 2011, 2011, M713. https://doi.org/10.3390/M713

AMA Style

Asiri AM, Khan SA, Khan KA. (2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone. Molbank. 2011; 2011(1):M713. https://doi.org/10.3390/M713

Chicago/Turabian Style

Asiri, Abdullah M., Salman A. Khan, and Khalid A. Khan. 2011. "(2E)-1-(2,5-Dimethyl-3-thienyl)-3-(4-nitrophenyl)propenone" Molbank 2011, no. 1: M713. https://doi.org/10.3390/M713

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