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  3. Volume 16, Number 1, 2022
  4. Synthesis of Heterocyclic Pyridine-Based Chalcones with Dimeric Structure

Synthesis of Heterocyclic Pyridine-Based Chalcones with Dimeric Structure

JCCT.
2022;
Volume 16, Number 1
: pp. 1–6
https://doi.org/10.23939/chcht16.01.001
Authors:
  1. Pui-Mun Lai
  2. Sie-Tiong Ha
1
Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti
2
Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat

Three new heterocyclic chalcones containing pyridine moiety were synthesized and their chemical structures were determined via IR, 1H NMR and 13C NMR spectroscopy. General name of these compounds are α,ω-bis{3-(pyridin-3-yl)-1-(phenyl-4-oxy)prop-2-en-1-one}alkanes. The chalcones are dimers having a symmetrical structure and they can be differed by the alkyl spacer length (CnH2n, where n = 8, 10 or 12). Differential scanning calorimetry (DSC) technique was employed to study their phase transition behaviors. DSC thermograms displayed direct isotropization and recrystallization during heating and cooling processes, respectively. The crystal phase turned into isotropic phase without exhibiting any mesophase. Influence of structure-liquid crystalline property relationships of the symmetrical dimers was examined in order to explain the reasons for the non-liquid crystalline properties in the current chalcones.

heterocycle
pyridine
chalcone
dimer
synthesis
  1. Achanta, G.; Modzelewska, A.; Feng, L.; Khan, S.R.; Huang P. A Boronic-Chalcone Derivative Exhibits Potent Anticancer Activity through Inhibition of the Proteasome. Mol. Pharmacol. 2005, 70, 426-433. https://doi.org/10.1124/mol.105.021311
  2. Bukhari, S.N.A.; Jasamai, M.; Jantan, I.; Ahmad, W. Review of Methods and Various Catalysts Used for Chalcone Synthesis. Mini Rev. Org. Chem. 2013, 10, 73-83. https://doi.org/10.2174/1570193X11310010006
  3. Bukhari, S.; Jasamai, M.; Jantan, I. Synthesis and Biological Evaluation of Chalcone Derivatives (Mini Review). Mini Rev. Med. Chem. 2012, 12, 1394-1403. https://doi.org/10.2174/138955712804586648
  4. Saydam, G.; Aydin, H.H.; Şahin, F.; Kucukoglu, O.; Erciyas, E.; Terzioglu, E.; Buyukkeçeci, F.; Omay, S.B. Cytotoxic and Inhibitory Effects of 4,4′-Dihydroxy Chalcone (RVC-588) on Proliferation of Human Leukemic HL-60 Cells. Leukemia Res. 2003, 27, 57-64. https://doi.org/10.1016/S0145-2126(02)00058-9
  5. Mishra, L.; Itokawa, H.; Bastow, K.F.; Tachibana, Y.; Nakanishi, Y.; Kilgore, N.; Lee, K.-H.; Sinha, R. Anti-HIV and Cytotoxic Activities of Ru(II)/Ru(III) Polypyridyl Complexes Containing 2,6-(2′-Benzimidazolyl)-pyridine/chalcone as Co-Ligand. Bioorg. Med. Chem. 2001, 9, 1667-1671. https://doi.org/10.1016/S0968-0896(01)00074-8
  6. Ko, H.-H.; Tsao, L.-T.; Yu, K.-L.; Liu, C.-T.; Wang, J.-P.; Lin, C.-N. Structure-Activity Relationship Studies on Chalcone Derivatives: The Potent Inhibition of Chemical Mediators Release. Bioorg. Med. Chem. 2003, 11, 105-111. https://doi.org/10.1016/S0968-0896(02)00312-7
  7. Tuchinda, P.; Reutrakul, V.; Claeson, P.; Pongprayoon, U.; Sematong, T.; Santisuk, T.; Taylor, W.C. Anti-Inflammatory Cyclohexenyl Chalcone Derivatives in Boesenbergia Pandurate. Phytochem. 2002, 59, 169-173. https://doi.org/10.1016/S0031-9422(01)00451-4
  8. Bukhari, S.N.A.; Jantan, I.B.; Jasamai, M.; Ahmad, W.; Amjad, M.W.B. Synthesis and Biological Evaluation of Curcumin Analogues. Mini Rev. Med. Chem. 2013, 13, 501-513. https://doi.org/10.3923/jms.2013.501.513
  9. Domínguez, J.N.; León, C.; Rodrigues, J.; de Domínguez, N.G.; Gut, J.; Rosenthal, P.J. Synthesis and Evaluation of New Antimalarial Phenylurenyl Chalcone Derivatives. J. Med. Chem. 2005, 48, 3654-3658. https://doi.org/10.1021/jm058208o
  10. Shin, D.-M.; Song, D.-M.; Jung, K.-H.; Moon, J.-H. Photochemical Transformation of Chalcone Derivatives. J. Photosci. 2001, 8, 9-12.
  11. Suwunwong, T. Syntheses and Fluorescent Properties of Chalcone Derivatives and Heteroarylchalcones. MSc thesis, Prince of Songkla University, Thailand, 2010.
  12. Chudgar, N.K.; Shah, S.N. New Fluorescent Mesogens with a Chalcone Central Linkage. Liq. Cryst. 1989, 4, 661-668. https://doi.org/10.1080/02678298908033201
  13. Yeap, G.-Y.; Susanti, I.; Teoh, B.-S.; Mahmood, W.A.K.; Harrison, W.T.A. Synthesis and Phase Transition in New Chalcone Derivatives: Crystal Structure of 1-Phenyl-3-(4′-undecylcarbonyloxyphenyl)-2-propen-1-one. Mol. Cryst. Liq. Cryst. 2005, 442, 133-146. https://doi.org/10.1080/154214090964753
  14. Thaker, B.T.; Patel, P.H.; Vansadiya, A.D.; Kanojiya, J.D. Substitution Effects on the Liquid Crystalline Properties of Thermotropic Liquid Crystals Containing Schiff Base Chalcone Linkages. Mol. Cryst. Liq. Cryst. 2009, 515, 135-147. https://doi.org/10.1080/15421400903291533
  15. https://doi.org/10.1080/15421400903291533
  16.  Ha, S.T.; Low, Y.W. Synthesis and Phase Transition Behaviours of New Chalcone Derivatives. J. Chem. 2013, 2013. https://doi.org/10.1155/2013/943723
  17. https://doi.org/10.1155/2013/943723
  18.  Lim, Y.-W.C.; Ha, S.-T.; Yeap, G.-Y.; Sastry, S.S. Synthesis and Mesomorphic Properties of New Heterocyclic Liquid Crystals with Central Ester-Chalcone Linkages. J. Taibah Univ. Sci. 2017, 11, 133-140. https://doi.org/10.1016/j.jtusci.2015.12.004
  19. https://doi.org/10.1016/j.jtusci.2015.12.004
  20. Collings, P.J.; Hilger, A. Liquid Crystal: Nature's Delicate Phase of Matter. IOP Publishing Ltd.: Bristol, 1990.
  21.  Yeap, G.-Y.; Al-Taifi, E.A.; Ong, C.-H.; Mahmood, W.A.K.; Takeuchi, D.; Ito, M.M. Synthesis and Phase Transition Studies on Non-Symmetric Liquid Crystal Dimers: N-(4-(n-(4-(Benzothiazol-2-yl)phenoxy)alkyloxy)-benzylidene)-4-chloroanilines. Phase Trans. 2012, 85, 483-496. https://doi.org/10.1080/01411594.2011.624278
  22. Prajapati, A.K.; Bonde, N.L.; Patel, H.N. Mesogenic Schiff's Base Ester with Chloroethyl Tail. Phase Trans. 2005, 78, 507-513. https://doi.org/10.1080/01411590500188876
  23. Parameswara Rao Alapati; Bhuyan, D.; Madhavi Latha, D.; Pardhasaradhi, P.; Pisipati, V.G.K.M.; Datta Prasad, P.V.; Singh, K.N. Study of Molecular Polarizabilities and Orientational Order Parameter in the Nematic Phase of 6.O12O.6 and 7.O12O.7. World J. Condens. Matt. Phys. 2011, 1, 167-174. https://doi.org/10.4236/wjcmp.2011.14025
  24. Gogoi, B.; Alapati, P.R.; Verma, A.L. Phase Transition Studies in Mesogenic Dimers. Cryst. Res. Technol. 2002, 37, 1331-1337. https://doi.org/10.1002/crat.200290010
  25. Yeap, G.-Y.; Hng, T.-C.; Takeuchi, D.; Osakada, K.; Mahmood, W.A.K.; Ito, M.M. Non-Symmetric Liquid Crystal Dimers: High Thermal Stability in Nematic Phase Enhanced by Thiophene-2-Carboxylate Moiety. Mol. Cryst. Liq. Cryst. 2009, 506, 134-149. https://doi.org/10.1080/15421400902987248
  26. Vill, V. Liquid Crystals, Molecular Design of: Calamitics. In Encyclopedia of Materials: Science and Technology; Buschow, K.H.J.; Cahn, R.W.; Flemings, M.C.; Ilschner, B.; Kramer, E.J.; Mahajan, S.; Veyssière, P., Eds.; Elsevier Science Ltd, 2001; pp 4545-4550. https://doi.org/10.1016/B0-08-043152-6/00796-8