Research Article
BibTex RIS Cite

4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi

Year 2021, Volume: 11 Issue: 4, 2870 - 2879, 15.12.2021
https://doi.org/10.21597/jist.902184

Abstract

Bu çalışmada, 4-((3-(triflorometil)piridin-2-il)oksi)benzohidrazit birimi bulunduran yedi yeni hidrazon türevlerinin sentezi gerçekleştirildi. Başlangıç bileşiği olarak kullanılan 4-hidroksibenzoik asit metanol içerisinde katalitik miktarda sülfürik asit ile metil esterine dönüştürüldü. Ester bileşiği, 2-bromo-3(triflorometil)piridin ile reaksiyona sokularak 4-((3-(triflorometil)piridin-2-il)oksi)benzoikasit metil esteri elde edildi. Daha sonra Ester bileşiği hidrazin hidrat ile hidrazitine dönüştürüldü. Hidrazit bileşiği seçilmiş sübstitüe aldehitler ile katılma-eliminasyon reaksiyonuna maruz bırakılarak hedef hidrazon türevleri sentezlendi. Sentezlenen bileşiklerin yapıları 1H, 13C NMR ve HRMS spektroskopileri ile aydınlatıldı. Toplamda dört kademe organik sentez, basit kimyasal modifikasyonlar, yüksek skalada sentezlenebilme, ucuz kimyasal reaktifler ve kısa sentez süreleri bu çalışmanın avantajları olarak belirlendi.

References

  • Andersen FA, 2008. Final amended report on the safety assessment of methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, and benzylparaben as used in cosmetic products. International Journal of Toxicology, 27: 1–82.
  • Backes GL, Neumann DM, Jursic BS, 2014. Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides. Bioorganic and Medicinal Chemistry, 22: 4629-4636.
  • Beaulieu PL, Coulombe R, Duan J, Fazal G, Godbout C, Hucke O, Jakalian A, Joly MA, Lepage O, Llinàs-Brunet M, Naud J, Poirier M, Rioux N, Thavonekham B, Kukolj G, Stammers TA, 2013. Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: Discovery of a quinazolinone chemotype. Bioorganic and Medicinal Chemistry Letters, 23: 4132–4140.
  • Bhole RP ve Bhusari KP, 2011. Synthesis, antihypertensive activity, and 3D-QSAR studies of some new p-hydroxybenzohydrazide derivatives. Archiv der Pharmazie Chemistry in Life Sciences, 2: 119–134.
  • Cukurovali A, Yilmaz I, Gur S, Kazaz C, 2006. Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring. European Journal of Medicinal Chemistry, 41: 201–207.
  • Cywin CL, Firestone RA, McNeil DW, Grygon CA, Crane KM, White DM, Kinkade PR, Hopkins JL, Davidson W, Labadia ME, Wildeson J, Morelock MM, Peterson JD, Raymond EL, Brown ML, and Spero DM, 2003. The Design of potent hydrazones and disulfides as cathepsin S inhibitors. Bioorganic and Medicinal Chemistry, 11: 733-740.
  • Evranos-Aksöz B, Baysal İ, Yabanoğlu-Çiftçi S, Djikic T, Yelekçi K, Uçar G, and Ertan R. 2015. Synthesis and Screening of Human Monoamine Oxidase-A Inhibitor Effect of New 2-Pyrazoline and Hydrazone Derivatives. Archiv der Pharmazie Chemistry in Life Sciences, 348: 743-756.
  • Lima PC, Lima LM, da Silva KCM, Léda PHO, de Miranda ALP, Fraga CAM, Barreiro EJ, 2000. Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole. European Journal of Medicinal Chemistry, 35: 187–203.
  • Lisina SV, Brel AK, Mazanova LS, Spasov AA, 2008. Synthesis and antipyretic activity of new salicylic acid derivatives. Pharmaceutical Chemistry Journal, 42: 574-576.
  • Mamolo MG, Falagiani V, Zampieri D, Vio L, Banfi E, Scialino G, 2003. Synthesis and antimycobacterial activity of (3,4-diaryl-3H-thiazol-2-ylidene)-hydrazide derivatives. Il Farmaco, 58: 631-637.
  • Nurkenov OA, Satpaeva ZB, Schepetkin IA, Khlebnikov AI, Turdybekov KM, Seilkhanov TM, Fazylov SD, 2017. Synthesis and biological activity of hydrazones of o- and p-hydroxybenzoic acids. Spatial structure of 5-bromo-2-hydroxybenzylidene-4-hydroxybenzohydrazide. Russian Journal of General Chemistry, 87: 2299–2306.
  • Oliveira PFM, Baron M, Chamayou A, Andre-Barres C, Guidetti B, Baltas M, 2014. Solvent-free mechanochemical route for green synthesis of pharmaceutically attractive phenolhydrazones. RSC Advances, 4: 56736–56742.
  • Periakaruppan P, Abraham R, Mahendran K, Ramanathan M, 2018. Simple synthesis of hydrazones with quorum quenching activity at room temperature in water. Environmental Chemistry Letters, 16: 1063-1067.
  • Raghav N. and Singh, M, 2014. SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H. Bioorganic and Medicinal Chemistry, 22: 4233-4245.
  • Rollas S ve Küçükgüzel ŞG, 2007. Biological Activities of Hydrazone Derivatives. Molecules, 12: 1910-1939.
  • Salgın-Gökşen U, Gökhan-Kelekçi N, Göktaş Ö, Köysal Y, Kılıç E. Işık Ş, Aktay G, Özalp M, 2007. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones,1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorganic and Medicinal Chemistry, 15: 5738–5751.
  • Sapra A, Kumar P, Kakkar S, Narasimhan B, 2014. Synthesis, antimicrobial evaluation and QSAR studies of p-hydroxy benzoic acid derivatives. Drug Research, 64: 17-22.
  • Siddiqui SM, Salahuddin A, Azam A, 2012. Synthesis, characterization and antiamoebic activity of some hydrazone and azole derivatives bearing pyridyl moiety as a promising heterocyclic scaffold. European Journal of Medicinal Chemistry, 49: 411-416.
  • Taha M, Ismail NH, Jamil W, Yousuf S, Jaafar FM, Ali MI, Kashif SM, Hussain E, 2013. Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones. Molecules, 18: 10912–10929.

Synthesis of New Hydrazone Derivatives Bearing 4-((3-(trifluoromethyl)pyridin-2- yl)oxy)benzohydrazide

Year 2021, Volume: 11 Issue: 4, 2870 - 2879, 15.12.2021
https://doi.org/10.21597/jist.902184

Abstract

In this work, seven new hydrazone derivatives containing 4-((3-(trifluoromethyl)pyridin-2-yl)oxy) benzohydrazide unit were synthesized. The 4-hydroxybenzoic acid used as the starting compound was converted to its methyl ester with a catalytic amount of sulfuric acid in methanol. The ester compound was reacted with 2-bromo-3-(trifluoromethyl)pyridine to give 4-((3-(trifluoromethyl)pyridin-2-yl)oxy)benzoic acid methyl ester. The ester compound was then converted to hydrazide with hydrazine hydrate. Target hydrazone derivatives were synthesized by reacting the hydrazide compound with selected substituted aldehydes via an addition-elimination reaction. The structures of the synthesized compounds were elucidated by 1H, 13C NMR and HRMS spectroscopies. In total, four steps of organic synthesis, simple chemical modifications, high-scaled synthesizing, cheap chemical reagents and short synthesis times were determined as the advantages of this study.

References

  • Andersen FA, 2008. Final amended report on the safety assessment of methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, and benzylparaben as used in cosmetic products. International Journal of Toxicology, 27: 1–82.
  • Backes GL, Neumann DM, Jursic BS, 2014. Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides. Bioorganic and Medicinal Chemistry, 22: 4629-4636.
  • Beaulieu PL, Coulombe R, Duan J, Fazal G, Godbout C, Hucke O, Jakalian A, Joly MA, Lepage O, Llinàs-Brunet M, Naud J, Poirier M, Rioux N, Thavonekham B, Kukolj G, Stammers TA, 2013. Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: Discovery of a quinazolinone chemotype. Bioorganic and Medicinal Chemistry Letters, 23: 4132–4140.
  • Bhole RP ve Bhusari KP, 2011. Synthesis, antihypertensive activity, and 3D-QSAR studies of some new p-hydroxybenzohydrazide derivatives. Archiv der Pharmazie Chemistry in Life Sciences, 2: 119–134.
  • Cukurovali A, Yilmaz I, Gur S, Kazaz C, 2006. Synthesis, antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring. European Journal of Medicinal Chemistry, 41: 201–207.
  • Cywin CL, Firestone RA, McNeil DW, Grygon CA, Crane KM, White DM, Kinkade PR, Hopkins JL, Davidson W, Labadia ME, Wildeson J, Morelock MM, Peterson JD, Raymond EL, Brown ML, and Spero DM, 2003. The Design of potent hydrazones and disulfides as cathepsin S inhibitors. Bioorganic and Medicinal Chemistry, 11: 733-740.
  • Evranos-Aksöz B, Baysal İ, Yabanoğlu-Çiftçi S, Djikic T, Yelekçi K, Uçar G, and Ertan R. 2015. Synthesis and Screening of Human Monoamine Oxidase-A Inhibitor Effect of New 2-Pyrazoline and Hydrazone Derivatives. Archiv der Pharmazie Chemistry in Life Sciences, 348: 743-756.
  • Lima PC, Lima LM, da Silva KCM, Léda PHO, de Miranda ALP, Fraga CAM, Barreiro EJ, 2000. Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole. European Journal of Medicinal Chemistry, 35: 187–203.
  • Lisina SV, Brel AK, Mazanova LS, Spasov AA, 2008. Synthesis and antipyretic activity of new salicylic acid derivatives. Pharmaceutical Chemistry Journal, 42: 574-576.
  • Mamolo MG, Falagiani V, Zampieri D, Vio L, Banfi E, Scialino G, 2003. Synthesis and antimycobacterial activity of (3,4-diaryl-3H-thiazol-2-ylidene)-hydrazide derivatives. Il Farmaco, 58: 631-637.
  • Nurkenov OA, Satpaeva ZB, Schepetkin IA, Khlebnikov AI, Turdybekov KM, Seilkhanov TM, Fazylov SD, 2017. Synthesis and biological activity of hydrazones of o- and p-hydroxybenzoic acids. Spatial structure of 5-bromo-2-hydroxybenzylidene-4-hydroxybenzohydrazide. Russian Journal of General Chemistry, 87: 2299–2306.
  • Oliveira PFM, Baron M, Chamayou A, Andre-Barres C, Guidetti B, Baltas M, 2014. Solvent-free mechanochemical route for green synthesis of pharmaceutically attractive phenolhydrazones. RSC Advances, 4: 56736–56742.
  • Periakaruppan P, Abraham R, Mahendran K, Ramanathan M, 2018. Simple synthesis of hydrazones with quorum quenching activity at room temperature in water. Environmental Chemistry Letters, 16: 1063-1067.
  • Raghav N. and Singh, M, 2014. SAR studies of differently functionalized chalcones based hydrazones and their cyclized derivatives as inhibitors of mammalian cathepsin B and cathepsin H. Bioorganic and Medicinal Chemistry, 22: 4233-4245.
  • Rollas S ve Küçükgüzel ŞG, 2007. Biological Activities of Hydrazone Derivatives. Molecules, 12: 1910-1939.
  • Salgın-Gökşen U, Gökhan-Kelekçi N, Göktaş Ö, Köysal Y, Kılıç E. Işık Ş, Aktay G, Özalp M, 2007. 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones,1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorganic and Medicinal Chemistry, 15: 5738–5751.
  • Sapra A, Kumar P, Kakkar S, Narasimhan B, 2014. Synthesis, antimicrobial evaluation and QSAR studies of p-hydroxy benzoic acid derivatives. Drug Research, 64: 17-22.
  • Siddiqui SM, Salahuddin A, Azam A, 2012. Synthesis, characterization and antiamoebic activity of some hydrazone and azole derivatives bearing pyridyl moiety as a promising heterocyclic scaffold. European Journal of Medicinal Chemistry, 49: 411-416.
  • Taha M, Ismail NH, Jamil W, Yousuf S, Jaafar FM, Ali MI, Kashif SM, Hussain E, 2013. Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones. Molecules, 18: 10912–10929.
There are 19 citations in total.

Details

Primary Language Turkish
Journal Section Kimya / Chemistry
Authors

Aytekin Köse 0000-0003-2448-3716

Publication Date December 15, 2021
Submission Date March 24, 2021
Acceptance Date June 29, 2021
Published in Issue Year 2021 Volume: 11 Issue: 4

Cite

APA Köse, A. (2021). 4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi. Journal of the Institute of Science and Technology, 11(4), 2870-2879. https://doi.org/10.21597/jist.902184
AMA Köse A. 4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi. J. Inst. Sci. and Tech. December 2021;11(4):2870-2879. doi:10.21597/jist.902184
Chicago Köse, Aytekin. “4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi”. Journal of the Institute of Science and Technology 11, no. 4 (December 2021): 2870-79. https://doi.org/10.21597/jist.902184.
EndNote Köse A (December 1, 2021) 4-(3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi. Journal of the Institute of Science and Technology 11 4 2870–2879.
IEEE A. Köse, “4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi”, J. Inst. Sci. and Tech., vol. 11, no. 4, pp. 2870–2879, 2021, doi: 10.21597/jist.902184.
ISNAD Köse, Aytekin. “4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi”. Journal of the Institute of Science and Technology 11/4 (December 2021), 2870-2879. https://doi.org/10.21597/jist.902184.
JAMA Köse A. 4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi. J. Inst. Sci. and Tech. 2021;11:2870–2879.
MLA Köse, Aytekin. “4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi”. Journal of the Institute of Science and Technology, vol. 11, no. 4, 2021, pp. 2870-9, doi:10.21597/jist.902184.
Vancouver Köse A. 4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi. J. Inst. Sci. and Tech. 2021;11(4):2870-9.