Next Article in Journal
4-[5-(2-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]benzohydrazide
Previous Article in Journal
3-(4-Amino-1,2,5-oxadiazol-3-yl)-4-(4-nitro-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

3,5-Bis(2-hydroxybenzylidene)piperidin-4-one

1
Department of Chemistry, Faculty of Mathematics and Narural Sciences, Padjadjaran University, Jalan Raya Bandung-Sumedang Km 21, Jatinangor 45363, Sumedang, Indonesia
2
Laboratory of Organic Synthesis, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Riau University, Pekanbaru, 26293, Indonesia
3
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 59100, Malaysia
4
Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, 1-23 Wakabamachi, Tsuruoka 997-8555, Japan
5
Department of Chemistry, Faculty of Matematics and Natural Sciences, Institut Teknology Bandung, Bandung 40132, Indonesia
*
Author to whom correspondence should be addressed.
Molbank 2014, 2014(2), M825; https://doi.org/10.3390/M825
Submission received: 24 March 2014 / Accepted: 20 May 2014 / Published: 26 May 2014

Abstract

:
The title compound, 3,5-bis(2-hydroxybenzylidene)piperidin-4-one (3), was prepared via reaction of 2-hydroxybenzaldehyde (1) and 4-piperidone (2) under microwave irradiation in the presence of 10% NaOH solution. The compound was fully characterized from its UV, IR, NMR and MS data.

Graphical Abstract

Curcumin is ubiquitous in many Curcuma species and is the major pigment found in the tumeric plant, Curcuma longa. Chemically, curcumin is a phenolic secondary metabolite known to possess anti-inflammatory [1], antioxidant [2], antiviral, anti-infective and anti-allergic activity [4], as well as anti-HIV [5] and anti-cancer [6] properties. Based on the wide range of its biological activities, curcumin has attracted much interst as a model for new target compounds to be synthesized. However, the isolation of curcuminoids from natural substances is low-yielding (3%–5% of the dry-weight), and in addition, the curcuminoids thus obtained possess limited structural variability. Indeed, this method presents an obstacle to optimize the function of curcumin [7]. Therefore, synthesis of curcumin analogues is a practical alternative to obtain a reasonable amount of material as well as a wider variety of structural features. These observation led to us to synthesize a new curcumin analog from 2-hydroxybenzaldehyde and 4-piperidone under microwave irradiation (Scheme 1).

Experimental

Synthesis of 3,5-Bis(2-hydroxybenzylidene)piperidin-4-one (3)

A mixture of 4-piperidone (0.4960 g, 0.01 mol), 2-hydroxybenzaldehyde (1.2212 g, 0.02 mol), 40% aq. NaOH (0.7 mL) and 95% EtOH (5 mL) was stirred at room temperature for 30 min, according to the partially modified procedure of a previous report [8]. The reaction mixture was subjected to microwave irradiation for 3 min at a power of 180 W and temperature of 60 °C. The reaction product was cooled and cold water was added. The precipitate formed was filtered and recrystallized from mixture of n-hexane-ethyl acetate to afford 3 (1.1128 g, 74%) as dark red crystals, m.p: 138 °C (decomp.). UV (MeOH) λmax: 316 (ε 6,100). IR (KBr) νmax cm−1: 3399, 3065, 1796, 1658 and 1600. 1H-NMR (Agilent DD2, 500 MHz, CDCl3): δ (ppm) 8.10 (2H, s), 6.87 (2H, dd, J = 7.7, 2.0 Hz), 6.77 (2H, dt, J = 7.5, 2.0 Hz), 6.17 (2H, d, J = 8 Hz), 5.91 (2H, t, J = 7.5 Hz), 3.86 (4H, s), 2.40 (1H, br.s). 13C-NMR (125 MHz, CDCl3): δ (ppm) 187.4, 174.0, 134.8, 130.9, 130.7, 128.9, 125.1, 124.5, 107.0, 49.4. HR-ESI-TOFMS: calculated for C19H18NO3 [M + H]+, m/z 308.1287, found m/z 308.1289.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgments

This research was partially supported by Directorate General of Hidgher Education, Ministry of Educatioan and Culture, Indonesia and University of Malaya Grant (UMRP) Malaysia, No. RP 001/2012A.

Author Contributions

Unang Supratman and Adel Zamri designed the whole experiment and contributed to the manuscript. Yoshihito Shino and Yana M. Syah measured the NMR and HR-ESITOFMS spectra. Yum Eryanti and Tati Herlina synthesize a new curcumin analog and wrote the manuscript. Khalijah Awang and Siti Nadiah Abdul Halim analyzed the NMR and HR-ESITOFMS spectra. All authors read and approved the final manuscript.

Conflicts of Interest

The authors declare no conflict of interst.

References

  1. Rostom, S.A.F.; Hassan, G.S.; El-Subbagh, H.I. Synthesis and biological evaluation of some polymethoxylated fused pyridine ring system as antitumor agents. Arch. Pharm. (Weinheim, Germany) 2009, 342, 584–590. [Google Scholar] [CrossRef] [PubMed]
  2. Dandia, A.; Jain, A.K.; Sharma, S. An efficient and highly selective approach for the construction of novel dispiro heterocycles in guanidine-based task-spesific [TMG][Ac] ionic liquid. Tetrahedron Lett. 2012, 53, 5859–5863. [Google Scholar] [CrossRef]
  3. Kumar, R.R.; Perumal, S.; Senthilkumar, P.; Yogeswari, P.; Stiram, D. An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles. Bioorg. Med. Chem. Lett. 2007, 17, 6459–6462. [Google Scholar] [CrossRef] [PubMed]
  4. Suzuki, M.; Nakamura, T.; Iyoki, S.; Fujiwara, A.; Watanabe, Y.; Mohri, K.; Isobe, K.; Ono, K.; Yano, S. Elucidation of anti-allergic activities of curcumin-related compounds with a special reference to their anti-oxidative activities. Biol. Pharm. Bull. 2005, 28, 1438–1443. [Google Scholar] [CrossRef] [PubMed]
  5. Handler, N.; Jaeger, W.; Puschacher, H.; Leiser, K.; Erker, T. Synthesis of Novel Curcumin Anologues and Their Evaluation as Selective Cyloxigenase-1(cox-1) Inhibitors. Chem. Pharm. Bull. 2007, 55, 64–71. [Google Scholar] [CrossRef] [PubMed]
  6. Babasaheb, Y.; Sebastian, T.; Rhonda, J.R.; Schumacher, N.; Diederich, Somer-Edgar, Tiffany, J.; Lesley, L. Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin. Bioorg. Med. Chem. 2010, 18, 6701–6707. [Google Scholar]
  7. Wichitnithad, W.; Nimmannit, U.; Wacharasindhu, S.; Rojsitthisak, P. Synthesis, Characterization and Biological Evalution of Succinate Pro-drugs of Curcuminoids for Colon Cancer Treatment. Molecules 2011, 16, 1888–1900. [Google Scholar] [CrossRef] [PubMed]
  8. Wu, J.; Zhang, Y.; Wang, J.; Weng, B.; Tang, Q.; Chen, X.; Pan, Z.; Liang, G.; Yang, S. Discovery and evaluation of piperid-4-one-containing mono-carbonyl analogs of curcumin as anti-inflammatory agents. Bioorg. Med. Chem. 2013, 21, 3058–3065. [Google Scholar] [CrossRef] [PubMed]
Scheme 1. The synthesis of 3,5-bis(2-hydroxybenzylidene)piperidin-4-one.
Scheme 1. The synthesis of 3,5-bis(2-hydroxybenzylidene)piperidin-4-one.
Molbank 2014 m825 sch001

Share and Cite

MDPI and ACS Style

Eryanti, Y.; Herlina, T.; Zamri, A.; Halim, S.N.A.; Shiono, Y.; Syah, Y.M.; Awang, K.; Supratman, U. 3,5-Bis(2-hydroxybenzylidene)piperidin-4-one. Molbank 2014, 2014, M825. https://doi.org/10.3390/M825

AMA Style

Eryanti Y, Herlina T, Zamri A, Halim SNA, Shiono Y, Syah YM, Awang K, Supratman U. 3,5-Bis(2-hydroxybenzylidene)piperidin-4-one. Molbank. 2014; 2014(2):M825. https://doi.org/10.3390/M825

Chicago/Turabian Style

Eryanti, Yum, Tati Herlina, Adel Zamri, Siti Nadiah Abdul Halim, Yoshihito Shiono, Yana M. Syah, Khalijah Awang, and Unang Supratman. 2014. "3,5-Bis(2-hydroxybenzylidene)piperidin-4-one" Molbank 2014, no. 2: M825. https://doi.org/10.3390/M825

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