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Synthesis and Structural Characterization of Some Novel Hydrazone Compounds Based on 2,4-Dinitrophenylhydrazine Containing Benzoyl Ester Group

Year 2022, Volume: 12 Issue: 1, 79 - 91, 30.06.2022
https://doi.org/10.55024/buyasambid.1135813

Abstract

Hydrazone compounds are important precursors employed to obtain candidate compounds in drug design studies. In the present study, benzoyl ester derivatives (1-5) derived from 4-(diethylamino) salicylaldehyde as a starting material were synthesized by reacting with substituted benzoyl chloride derivatives (benzoyl chloride, 2-nitrobenzoyl chloride, 3-nitrobenzoyl chloride, 4-nitrobenzoyl chloride and 3,5-dinitrobenzoyl chloride) in a 1:1 mole ratio in pyridine as a solvent. A new series of hydrazone compounds (6-10) were synthesized by the condensation reaction of 2,4-dinitrophenylhydrazine with the obtained benzoyl esters, and the structural characterization of these compounds was clarified by FT-IR, 1H NMR, 13C NMR and elemental analysis. As a result, it is thought that these compounds may show biological activities.

References

  • Angelova, V., Karabeliov, V., Andreeva‐Gateva, P. A., Tchekalarova, J. (2016). Recent developments of hydrazide/hydrazone derivatives and their analogs as anticonvulsant agents in animal models. Drug Development Research, 77, 379-392.
  • Asif, M., Husain, A. (2013). Analgesic, anti-inflammatory, and antiplatelet profile of hydrazones containing synthetic molecules. Journal of Applied Chemistry, 2013, 1-7.
  • Başaran, E., Haşimi, N., Çakmak, R., Çınar, E. (2022). Synthesis, structural characterization, and biological evaluation of some hydrazone compounds as potential antioxidant agents. Russian Journal of Bioorganic Chemistry, 48, 143-152.
  • Bingul, M., Ercan, S., Boga, M. (2020). The design of novel 4, 6-dimethoxyindole based hydrazide-hydrazones: Molecular modeling, synthesis and anticholinesterase activity. Journal of Molecular Structure, 1213, 128202.
  • Çakmak, R., Başaran, E., Kaya, S., Erkan, S. (2022). Synthesis, spectral characterization, chemical reactivity and anticancer behaviors of some novel hydrazone derivatives: experimental and theoretical insights. Journal of Molecular Structure, 1253, 132224.
  • Çakmak, R., Çınar, E., Başaran, E., Boğa, M. (2021). Synthesis, characterization and biological evaluation of ester derivatives of 4-(diethylamino) salicylaldehyde as cholinesterase, and tyrosinase inhibitors. Middle East Journal of Science, 7, 137-144.
  • Çınar, E., Başaran, E., Erdoğan, Ö., Çakmak, R., Boğa, M., Çevik, Ö. (2021). Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies. Journal of the Chinese Chemical Society, 68, 2355-2367.
  • Haghighijoo, Z., Firuzi, O., Hemmateenejad, B., Emami, S., Edraki, N., Miri, R. (2017). Synthesis and biological evaluation of quinazolinone-based hydrazones with potential use in Alzheimer’s disease. Bioorganic Chemistry, 74, 126-133.
  • Kamalı, A., Çakmak, R., Boğa, M. (2022). Anticholinesterase and antioxidant activities of novel heterocyclic Schiff base derivatives containing an aryl sulfonate moiety. Journal of the Chinese Chemical Society, 69, 731-743.
  • Naveen Kumar, H. S., Parumasivam, T., Jumaat, F., Ibrahim, P., Asmawi, M. Z., Sadikun, A. (2014). Synthesis and evaluation of isonicotinoyl hydrazone derivatives as antimycobacterial and anticancer agents. Medicinal Chemistry Research, 23, 269-279.
  • Rollas, S., Güniz Küçükgüzel, Ş. (2007). Biological activities of hydrazone derivatives. Molecules, 12, 1910-1939.
  • Shirinzadeh, H., Altanlar, N., Yucel, N., Ozden, S., Suzen, S. (2011). Antimicrobial evaluation of indole-containing hydrazone derivatives. Zeitschrift für Naturforschung C, 66, 340-344.
  • Singh, N., Ranjana, R., Kumari, M., Kumar, B. (2016). A review on biological activities of hydrazone derivatives. International Journal of Pharmaceutical and Clinical Research, 8, 162-166.
  • Surov, A. O., Voronin, A. P., Simagina, A. A., Churakov, A. V., Perlovich, G. L. (2016). Pharmaceutical salts of biologically active hydrazone compound salinazid: Crystallographic, solubility, and thermodynamic aspects. Crystal Growth & Design, 16, 2605-2617.
  • Ul Ain, N., Ansari, T. M., Shah Gilani, M. R. H., Xu, G., Liang, G., Luque, R., Alsaiari, M., Jalalah, M. (2022). Facile and straightforward synthesis of hydrazone derivatives. Journal of Nanomaterials, 2022.
  • Wang, Y., Yihuo, A., Wang, L., Dong, S., Feng, X. (2022). Catalytic asymmetric synthesis of chiral azo compounds via interrupted Japp-Klingemann reaction with aryldiazonium salts. Science China Chemistry, 65, 546-553.

Benzoil Ester Grubu İçeren 2,4-Dinitrofenilhidrazin Temelli Bazı Yeni Hidrazon Bileşiklerinin Sentezi ve Yapısal Karakterizasyonu

Year 2022, Volume: 12 Issue: 1, 79 - 91, 30.06.2022
https://doi.org/10.55024/buyasambid.1135813

Abstract

Hidrazon bileşikleri, ilaç tasarımı çalışmalarında aday bileşikleri elde etmek için kullanılan önemli öncülerdir. Bu çalışmada, başlangıç materyali olarak 4-(dietilamino) salisilaldehitten türetilen benzoil ester türevleri (1-5) sübstitüe benzoil klorür türevleri (benzoil klorür, 2-nitrobenzoil klorür, 3-nitrobenzoil klorür, 4-nitrobenzoil klorür ve 3,5-dinitrobenzoil klorür) ile çözücü olarak piridin ortamında 1:1 mol oranında reaksiyona girmesiyle sentezlendi. Elde edilen benzoil esterler ile 2,4-dinitrofenilhidrazinin kondenzasyon reaksiyonu ile yeni bir dizi hidrazon bileşikleri (6-10) sentezlendi ve bu bileşikler yapısal karakterizasyonu FT-IR, 1H NMR, 13C NMR ve element analizi aydınlatıldı. Sonuç olarak, bu bileşiklerin biyolojik aktiviteler gösterebileceği düşünülmektedir.

References

  • Angelova, V., Karabeliov, V., Andreeva‐Gateva, P. A., Tchekalarova, J. (2016). Recent developments of hydrazide/hydrazone derivatives and their analogs as anticonvulsant agents in animal models. Drug Development Research, 77, 379-392.
  • Asif, M., Husain, A. (2013). Analgesic, anti-inflammatory, and antiplatelet profile of hydrazones containing synthetic molecules. Journal of Applied Chemistry, 2013, 1-7.
  • Başaran, E., Haşimi, N., Çakmak, R., Çınar, E. (2022). Synthesis, structural characterization, and biological evaluation of some hydrazone compounds as potential antioxidant agents. Russian Journal of Bioorganic Chemistry, 48, 143-152.
  • Bingul, M., Ercan, S., Boga, M. (2020). The design of novel 4, 6-dimethoxyindole based hydrazide-hydrazones: Molecular modeling, synthesis and anticholinesterase activity. Journal of Molecular Structure, 1213, 128202.
  • Çakmak, R., Başaran, E., Kaya, S., Erkan, S. (2022). Synthesis, spectral characterization, chemical reactivity and anticancer behaviors of some novel hydrazone derivatives: experimental and theoretical insights. Journal of Molecular Structure, 1253, 132224.
  • Çakmak, R., Çınar, E., Başaran, E., Boğa, M. (2021). Synthesis, characterization and biological evaluation of ester derivatives of 4-(diethylamino) salicylaldehyde as cholinesterase, and tyrosinase inhibitors. Middle East Journal of Science, 7, 137-144.
  • Çınar, E., Başaran, E., Erdoğan, Ö., Çakmak, R., Boğa, M., Çevik, Ö. (2021). Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies. Journal of the Chinese Chemical Society, 68, 2355-2367.
  • Haghighijoo, Z., Firuzi, O., Hemmateenejad, B., Emami, S., Edraki, N., Miri, R. (2017). Synthesis and biological evaluation of quinazolinone-based hydrazones with potential use in Alzheimer’s disease. Bioorganic Chemistry, 74, 126-133.
  • Kamalı, A., Çakmak, R., Boğa, M. (2022). Anticholinesterase and antioxidant activities of novel heterocyclic Schiff base derivatives containing an aryl sulfonate moiety. Journal of the Chinese Chemical Society, 69, 731-743.
  • Naveen Kumar, H. S., Parumasivam, T., Jumaat, F., Ibrahim, P., Asmawi, M. Z., Sadikun, A. (2014). Synthesis and evaluation of isonicotinoyl hydrazone derivatives as antimycobacterial and anticancer agents. Medicinal Chemistry Research, 23, 269-279.
  • Rollas, S., Güniz Küçükgüzel, Ş. (2007). Biological activities of hydrazone derivatives. Molecules, 12, 1910-1939.
  • Shirinzadeh, H., Altanlar, N., Yucel, N., Ozden, S., Suzen, S. (2011). Antimicrobial evaluation of indole-containing hydrazone derivatives. Zeitschrift für Naturforschung C, 66, 340-344.
  • Singh, N., Ranjana, R., Kumari, M., Kumar, B. (2016). A review on biological activities of hydrazone derivatives. International Journal of Pharmaceutical and Clinical Research, 8, 162-166.
  • Surov, A. O., Voronin, A. P., Simagina, A. A., Churakov, A. V., Perlovich, G. L. (2016). Pharmaceutical salts of biologically active hydrazone compound salinazid: Crystallographic, solubility, and thermodynamic aspects. Crystal Growth & Design, 16, 2605-2617.
  • Ul Ain, N., Ansari, T. M., Shah Gilani, M. R. H., Xu, G., Liang, G., Luque, R., Alsaiari, M., Jalalah, M. (2022). Facile and straightforward synthesis of hydrazone derivatives. Journal of Nanomaterials, 2022.
  • Wang, Y., Yihuo, A., Wang, L., Dong, S., Feng, X. (2022). Catalytic asymmetric synthesis of chiral azo compounds via interrupted Japp-Klingemann reaction with aryldiazonium salts. Science China Chemistry, 65, 546-553.
There are 16 citations in total.

Details

Primary Language Turkish
Journal Section Research Article
Authors

Reşit Çakmak 0000-0003-0401-7419

Eyüp Başaran 0000-0002-7840-5919

Publication Date June 30, 2022
Submission Date June 25, 2022
Acceptance Date June 27, 2022
Published in Issue Year 2022 Volume: 12 Issue: 1

Cite

APA Çakmak, R., & Başaran, E. (2022). Benzoil Ester Grubu İçeren 2,4-Dinitrofenilhidrazin Temelli Bazı Yeni Hidrazon Bileşiklerinin Sentezi ve Yapısal Karakterizasyonu. Batman Üniversitesi Yaşam Bilimleri Dergisi, 12(1), 79-91. https://doi.org/10.55024/buyasambid.1135813