Araştırma Makalesi

Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold

Cilt: 14 Sayı: 1 1 Mart 2024
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Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold

Öz

2,3-disubstituted acrylonitriles derivatives are among the most important molecules in medicinal chemistry due to their bioactivity and their role as starting compounds for many bioactive molecules. Many heterocyclic structures have been investigated as AChE enzyme inhibitors. Nowadays, E/Z acrylonitrile derivatives are being studied as new AChE inhibitors. This study aimed to synthesis new heteroaryl-acrylonitrile compounds using Knoevenagel condensation. In this context, acrylonitrile compounds with aryl and heteroaryl structures at positions 2 and 3 (respectively )were synthesized from the reactions of pyrazole aldehyde derivative (4) with various acetonitrile compounds. Synthesized novel heteroarylacrylonitrile derivatives (5a-d) containing pyrazole ring are potential AChE inhibitors. The structures of the synthesized compounds were elucidated by FTIR, 1H-NMR and 13C-NMR spectroscopic techniques.

Anahtar Kelimeler

Teşekkür

I would like to thank Akdeniz University and Atatürk University Chemistry Departments for spectroscopic measurements.

Kaynakça

  1. Abu-Hashem, A. A., Gouda, M. A., & Badria, F. A. (2010). Synthesis of some new pyrimido[2’,1’:2,3]thiazolo[4,5-b]quinoxaline derivatives as anti-inflammatory and analgesic agents. European Journal of Medicinal Chemistry, 45(5), 1976-1981. https://doi.org/10.1016/J.EJMECH.2010.01.042
  2. Anas, S. (2022). Synthesis and biological activity studies of some 3-aryl-2-(4-(substituted phenyl)thiazol-2-yl)acrylonitrile derivatives, Hacettepe Üniversitesi, Sağlık Bilimleri Enstitüsü, Farmasötik Kimya Ana Bilim Dalı, Yüksek lisans Tezi, Ankara.
  3. Biçer, A., & Altundaş, R. (2023). Formylation reactions of N-protecting 2-Amino-4-phenyl thiazole compounds. Journal of Molecular Structure, 1289, 135840. https://doi.org/10.1016/J.MOLSTRUC.2023.135840
  4. Biçer, A., Cin, G., & Yakalı, G. (2022). Prediction of the Charge Transport and Electronic Properties of Two Pyrazole Derivatives in terms of Their Solid Molecular Arrangements and Reorganization Energy: The Effects of Nitro Groups on Structure-Property Relationship. Authorea. September 27, 2022. https://doi.org/10.22541/au.166425484.40387842/v1
  5. De La Torre, P., Saavedra, L. A., Caballero, J., Quiroga, J., Alzate-Morales, J. H., Cabrera, M. G., & Trilleras, J. (2012a). A Novel Class of Selective Acetylcholinesterase Inhibitors: Synthesis and Evaluation of (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles. Molecules 2012, Vol. 17, Pages 12072-12085, 17(10), 12072–12085. https://doi.org/10.3390/MOLECULES171012072
  6. De La Torre, P., Saavedra, L. A., Caballero, J., Quiroga, J., Alzate-Morales, J. H., Cabrera, M. G., & Trilleras, J. (2012b). A novel class of selective acetylcholinesterase inhibitors: Synthesis and evaluation of (E)-2-(benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles. Molecules, 17(10), 12072-12085. https://doi.org/10.3390/MOLECULES171012072
  7. De-La-Torre, P., Treuer, A. V., Gutierrez, M., Poblete, H., Alzate-Morales, J. H., Trilleras, J., Astudillo-Saavedra, L., & Caballero, J. (2016). Synthesis and in silico analysis of the quantitative structure–activity relationship of heteroaryl–acrylonitriles as AChE inhibitors. Journal of the Taiwan Institute of Chemical Engineers, 59, 45-60. https://doi.org/10.1016/J.JTICE.2015.07.022
  8. Fringuelli, F., Pani, G., Piermatti, O., & Pizzo, F. (1994). Condensation reactions in water of active methylene compounds with arylaldehydes. One-pot synthesis of flavonols. Tetrahedron, 50(39), 11499-11508. https://doi.org/10.1016/S0040-4020(01)89287-5

Ayrıntılar

Birincil Dil

İngilizce

Konular

Organik Kimyasal Sentez

Bölüm

Araştırma Makalesi

Erken Görünüm Tarihi

20 Şubat 2024

Yayımlanma Tarihi

1 Mart 2024

Gönderilme Tarihi

8 Ağustos 2023

Kabul Tarihi

1 Kasım 2023

Yayımlandığı Sayı

Yıl 2024 Cilt: 14 Sayı: 1

Kaynak Göster

APA
Biçer, A. (2024). Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold. Journal of the Institute of Science and Technology, 14(1), 326-332. https://doi.org/10.21597/jist.1339475
AMA
1.Biçer A. Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold. Iğdır Üniv. Fen Bil Enst. Der. 2024;14(1):326-332. doi:10.21597/jist.1339475
Chicago
Biçer, Abdullah. 2024. “Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold”. Journal of the Institute of Science and Technology 14 (1): 326-32. https://doi.org/10.21597/jist.1339475.
EndNote
Biçer A (01 Mart 2024) Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold. Journal of the Institute of Science and Technology 14 1 326–332.
IEEE
[1]A. Biçer, “Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold”, Iğdır Üniv. Fen Bil Enst. Der., c. 14, sy 1, ss. 326–332, Mar. 2024, doi: 10.21597/jist.1339475.
ISNAD
Biçer, Abdullah. “Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold”. Journal of the Institute of Science and Technology 14/1 (01 Mart 2024): 326-332. https://doi.org/10.21597/jist.1339475.
JAMA
1.Biçer A. Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold. Iğdır Üniv. Fen Bil Enst. Der. 2024;14:326–332.
MLA
Biçer, Abdullah. “Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold”. Journal of the Institute of Science and Technology, c. 14, sy 1, Mart 2024, ss. 326-32, doi:10.21597/jist.1339475.
Vancouver
1.Abdullah Biçer. Synthesis and Characterization of Novel Heteroarylacrylonitrile Derivatives Containing Pyrazole Scaffold. Iğdır Üniv. Fen Bil Enst. Der. 01 Mart 2024;14(1):326-32. doi:10.21597/jist.1339475

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