Yıl: 2021 Cilt: 14 Sayı: 1 Sayfa Aralığı: 39 - 47 Metin Dili: İngilizce DOI: 10.25135/acg.oc.95.21.01.1942 İndeks Tarihi: 24-06-2021

Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene

Öz:
In this study, a new series consisting of 12 heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzenewere synthesised. Chalcones were synthesised in high purity and efficiency, via condensation of mono, bis and tris2,4,6-trimethoxy acetophenones with hetero-2-carbaldehyde derivatives based on Claisen Schdmit condensation. Thereactions feature a good scope for the all products, mild reaction conditions and good yields. The synthesizedcompounds were characterized by using FT-IR, NMR and elemental analysis spectroscopic techniques.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • [1] Gomes, M. N.; Muratov, E. N.; Pereira, M.; Peixoto, J. C.; Rosseto, L. P.; Cravo, P. V. L.; Andrade, C. H.; Neves, B. J. Chalcone derivatives: promising starting points for drug design. Molecules 2017, 22, p. 1210.
  • [2] Sahu, N. K.; Balbhadra, S. S.; Choudhary, J.; Kohli, D. V. Exploring pharmacological significance of chalcone scaffold: a review. Curr. Med. Chem. 2012, 19, 209-25.
  • [3] Kumar, C. C. S.; Loh, W. S.; Ooi, C. W.; Quah, C. K.; Fun, H. K. Heteroaryl chalcones: design, synthesis, X-ray crystal structures and biological evaluation. Molecules 2013, 18, 12707-12724.
  • [4] Mathew, B.; Suresh, J.; Anbazghagan, S.; Paulraj, J.; Krishnan, G. K. Heteroaryl chalcones: mini review about their therapeutic voyage. Biomed. Prev. Nutr. 2014, 4, 451-458.
  • [5] Go, M. L.; Wu, X.; Liu, X. L. Chalcones: an update on cytotoxic and chemoprotective properties. Curr. Med. Chem. 2005, 12, 481-499.
  • [6] Nowakowska, Z. A review of anti-infective and anti-inflammatory chalcones. Eur. J. Med. Chem. 2007, 42, 125-137.
  • [7] PanneerSelvam, T.; Karthick, V.; Vijayaraj Kumar, P.; Ashraf Ali, M. Antiepileptic activity of novel 2- (substituted benzylidene)-7-(4- fluorophenyl)-5-(furan-2-yl)-2H-thiazolo[3,2-a]pyrimidin-3(7H)-one derivatives. Lett. Drug Des. Discov. 2013, 10, 204-211.
  • [8] Zhang, H. J.; Zhu, Di-Di; Li, Z. L.; Sun, J.; Zhu, H. L. Synthesis, molecular modeling and biological evaluation of β-ketoacyl-acyl carrier protein synthase III (FabH) as novel antibacterial agents. Bioorg. Med. Chem. 2011, 19, 4513-4519.
  • [9] Swift, L. H.; Golsteyn, R. M. Genotoxic anti-cancer agents and their relationship to DNA damage, mitosis, and checkpoint adaptation in proliferating cancer cells. Int. J. Mol. Sci. 2014, 15, 3403-3431.
  • [10] Meng, C. Q.; Ni, L.; Worsencroft, K. J.; Ye, Z.; Weingarten, M. D.; Simpson, J. E.; Skudlarek, J. W.; Marino, E. M.; Suen, K. L.; Kunsch, C.; Souder, A.; Howard, R. B.; Sundell, C. L.; Wasserman, M. A.; Sikorski, J. A. Carboxylated, heteroaryl-substituted chalcones as inhibitors of vascular cell adhesion molecule-1 expression for use in chronic inflammatory diseases. J. Med. Chem. 2007, 50, 1304-1315.
  • [11] Lee, I. S. H.; Jeoung, E. J.; Lee, C. K. Synthesis and NMR studies of (E)-1-aryl-3-(2-pyrrolyl)-2- propenones and (E)-3-aryl-1-(2-pyrrolyl)-2-propenones. Bull. Korean Chem. Soc. 2013, 34, 936-942.
  • [12] Fandakh, S.; Doğan, S.; Sellitepe, H. E.; Yaşar, A.; Yayh, N. Synthesis, theoretical calculation and αglucosidase inhibition of new chalcone oximes. Org. Commun. 2018, 11, 23-34.
  • [13] Kurpil, B.; Otte, K.; Mishchenko, A.; Lamagni, P.; Lipiński, W.; Lock, N.; Antonietti, M.; Savateev, A. Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields Nfused pyrroles. Nat. Commun. 2019, 10, p. 945.
  • [14] Suwunwong, T.; Chantrapromma, S.; Fun, H. K. Influence of trimethoxy-substituted positions on fluorescence of heteroaryl chalcone derivatives. Chem. Pap. 2011, 65, 890-897.
  • [15] Ciupa, A.; Griffiths, N. J.; Light, S. K.; Wood, P. J.; Caggiano, L. Design, synthesis and antiproliferative activity of urocanic-chalcone hybrid derivatives. Med. Chem. Comm. 2011, 2, 1011-1015.
  • [16] Burmaoglu, S.; Yilmaz, A. O.; Polat, M. F.; Kaya, R.; Gulcin, İ.; Algul, O. Synthesis and biological evaluation of novel tris-chalcones as potent carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase and α-glycosidase inhibitors. Bioorg. Chem. 2019, 85, 191-197.
  • [17] Ardiansah, B. Chalcones bearing N, O, and S-heterocycles: recent notes on their biological significances. J. Appl. Pharm. Sci. 2019, 9, 117-129.
  • [18] Krishna Prasad, C.; Machiraju, P. V. S. Synthesis and characterization of some novel aryl and heteroaryl chalcone derivatives of 3-(3,4,5-trimethoxyphenyl)-1-phenyl-1h-pyrazole-4-carbaldehyde for assessing their potentials as anticancer agents. Russ. J. Gen. Chem. 2017, 87, 2056-2066.
  • [19] Tsukerman, S. V.; Izvekov, V. P.; Lavrushin Khimiya, V. F. Synthesis of chalcone analogs containing a pyrrole ring. Khim. Geterotsikl. Soedin. 1965, 1, 527-530.
  • [20] Roy, T.; Boateng, S. T.; Banang-Mbeumi, S.; Singh, P. K.; Basnet, P.; Chamcheu, R. C. N.; Ladu, F.; Chauvin, I.; Spiegelman, V. S.; Hill, R. A.; Kousoulas, K. G.; Nagalo, B. M.; Walker, A. L.; Fotie, J.; Murru, S.; Sechi, M.; Chamcheu, J. C. Synthesis, inverse docking-assisted identification and in vitro biological characterization of flavonol-based analogs of fisetin as c-Kit, CDK2 and MTOR inhibitors against melanoma and non-melanoma skin cancers. Bioorg. Chem. 2021, 107. https://doi.org/10.1016/j.bioorg.2020.104595.
  • [21] Zhang, L.; Yang, C.; Huang, Y.; Huang, H.; Yuan, X.; Zhang, P.; Ye, C.; Wei, M.; Wang, Y.; Luo, X.; Luo, J. Cardamonin inhibits the growth of human osteosarcoma cells through activating P38 and JNK signaling pathway. Biomed. Pharmacother. 2021, 134. https://doi.org/10.1016/j.biopha.2020.111155.
  • [22] Salgin-Goksen, U.; Telli, G.; Erikci, A.; Dedecengiz, E.; Tel, B. C.; Kaynak, F. B.; Yelekci, K.; Ucar, G.; Gokhan-Kelekci, N. New 2-pyrazoline and hydrazone derivatives as potent and selective monoamine oxidase A inhibitors. J. Med. Chem. 2021, 64, 1989-2009.
APA POLAT M, AKTAS ANIL D (2021). Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. , 39 - 47. 10.25135/acg.oc.95.21.01.1942
Chicago POLAT M. Fatih,AKTAS ANIL DERYA Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. (2021): 39 - 47. 10.25135/acg.oc.95.21.01.1942
MLA POLAT M. Fatih,AKTAS ANIL DERYA Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. , 2021, ss.39 - 47. 10.25135/acg.oc.95.21.01.1942
AMA POLAT M,AKTAS ANIL D Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. . 2021; 39 - 47. 10.25135/acg.oc.95.21.01.1942
Vancouver POLAT M,AKTAS ANIL D Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. . 2021; 39 - 47. 10.25135/acg.oc.95.21.01.1942
IEEE POLAT M,AKTAS ANIL D "Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene." , ss.39 - 47, 2021. 10.25135/acg.oc.95.21.01.1942
ISNAD POLAT, M. Fatih - AKTAS ANIL, DERYA. "Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene". (2021), 39-47. https://doi.org/10.25135/acg.oc.95.21.01.1942
APA POLAT M, AKTAS ANIL D (2021). Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. Organic Communications, 14(1), 39 - 47. 10.25135/acg.oc.95.21.01.1942
Chicago POLAT M. Fatih,AKTAS ANIL DERYA Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. Organic Communications 14, no.1 (2021): 39 - 47. 10.25135/acg.oc.95.21.01.1942
MLA POLAT M. Fatih,AKTAS ANIL DERYA Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. Organic Communications, vol.14, no.1, 2021, ss.39 - 47. 10.25135/acg.oc.95.21.01.1942
AMA POLAT M,AKTAS ANIL D Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. Organic Communications. 2021; 14(1): 39 - 47. 10.25135/acg.oc.95.21.01.1942
Vancouver POLAT M,AKTAS ANIL D Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene. Organic Communications. 2021; 14(1): 39 - 47. 10.25135/acg.oc.95.21.01.1942
IEEE POLAT M,AKTAS ANIL D "Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene." Organic Communications, 14, ss.39 - 47, 2021. 10.25135/acg.oc.95.21.01.1942
ISNAD POLAT, M. Fatih - AKTAS ANIL, DERYA. "Synthesis and characterization of novel mono, bis and tris heteroaryl chalcone derivatives of 1,3,5-trimethoxybenzene". Organic Communications 14/1 (2021), 39-47. https://doi.org/10.25135/acg.oc.95.21.01.1942