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Synthesis, Antibacterial Activity and Photophysical Properties of Bis-benzamide derivatives

Yıl 2021, , 143 - 149, 01.09.2021
https://doi.org/10.52794/hujpharm.993718

Öz

In this study, N,N’-(dodecane-1,12-diyl)bis(2,4-dichlorobenzamide) and N,N’- (dodecane-1,12-diyl)bis(4-bromobenzamide) as new bis-benzamides were syn- thesized by reaction of 1,12-diaminododecane and two different acyl chloride compounds in 88% and 92% yield, respectively. Their molecular structures were characterized using 1H NMR, 13C NMR and FT-IR techniques. Antibacterial activities of the synthesized compounds were screened against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 strains. Moreover, pho- tophysical properties of the products in CH Cl and CHCl were investigated us-
2 2 3
ing UV-vis spectroscopy. The compound 3a exhibited positive solvatochromism
about 31 nm by increasing of solvent polarity.

Destekleyen Kurum

Mersin University Research Fund

Proje Numarası

BAP 2020-1-AP5-4097

Teşekkür

This work was funded by Mersin University Research Fund (Project No: BAP 2020-1-AP5-4097).

Kaynakça

  • 1- Wei G, Huang L, Jiang Y, Shen Y, Huang Z, Huang Y, Sun X, Zhao C: Lenvatinib-zinc phthalocyanine conjugates as potential agents for enhancing synergistic therapy of multidrug-resistant cancer by glutathione depletion. Eur. J. Med. Chem. 2019, 169: 53-64.
  • 2- Lopéz-Martínez LM, García-Elías J, Ochoa-Terán A, Ortega HS, Ochoa-Lara K, Montaño-Medina CU, Yatsimirsky AK, Ramírez J, Labastida-Galván V, Ordoñez M: Synthesis, characterization and anion recognition studies of new fluorescent alkyl bis (naphthylureylbenzamide)-based receptors. Tetrahedron 2020, 76: 130815.
  • 3- García-Elías J, Ochoa-Terán A, Yatsimirsky AK, Ortega HS, Ochoa-Lara K, López-Martínez LM, Castro- Riquelme CL, Garcí ÁL, Madrigal-Peralta D, Labastida-Galván V, Ordoñez M: Synthesis and anion recognition studies of new oligomethylene bis (nitrophenylureylbenzamide) receptors. RSC Adv. 2019, 9: 39147-39162.
  • 4- Pina-Luis G, Ochoa-Teran A, Rivero IA: Solid phase synthesis of N-alkyl-bis-o-aminobenzamides for metal ion sensing based on a fluorescent dansyl platform. J. Comb. Chem. 2009, 11: 83-90.
  • 5- Winstanley KJ, Smith DK: Ortho-substituted catechol derivatives: the effect of intramolecular hydrogen-bonding pathways on chloride anion recognition. J. Org. Chem. 2007, 72: 2803-2815.
  • 6- Nguyen M, Meunier B, Robert A: Catechol‐Based Ligands as Potential Metal Chelators Inhibiting Redox Activity in Alzheimer's Disease. Eur. J. Inorg. Chem. 2017, 2017: 3198-3204.
  • 7- Wang J, Hong G, Li G, Wang W, Liu T: Novel homo-bivalent and polyvalent compounds based on ligustrazine and heterocyclic ring as anticancer agents. Molecules 2019, 24: 4505.
  • 8- Filatov AS, Knyazev NA, Shmakov SV, Bogdanov AA, Ryazantsev MN, Shtyrov AA, Starova GL, Malchanov AP, Larina AG, Boitsov VM, Stepakov AV: Concise synthesis of tryptanthrin spiro analogues with in vitro antitumor activity based on one-pot, three-component 1,3-dipolar cycloaddition of azomethine ylides to сyclopropenes. Synthesis 2019, 51: 713-729.
  • 9- Dodo K, Minato T, Hashimoto Y: Structure–activity relationship of bis-galloyl derivatives related to (−)-epigallocatechin gallate. Chemical and Pharmaceutical Bulletin 2009, 57: 190-194.
  • 10- Nguyen TX, Morrell A, Conda-Sheridan M, Marchand C, Agama K, Bermingam A, Stephen AG, Chergui A, Naumova A, Fisher R, O’Keefe BR, Pommier Y, Cushman M: Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase I (Tdp1)–topoisomerase I (Top1) inhibitors. J. Med. Chem. 2012, 55: 4457-4478.
  • 11- Al-Masoudi NA, Al-Haidery N, Faili NT, Pannecouque C: Amino acid derivatives. Part 5. Synthesis and anti-HIV activity of new sebacoyl precursor derived thioureido-amino acid and phthalimide derivatives. Arkivoc 2010, 2010: 185-195.
  • 12- Rivero-Buceta E, Carrero P, Doyagüez EG, Madrona A, Quesada E, Camarasa MJ, Pérez- Pérez MJ, Leyssen P, Paeshuyse J, Balzarini J, Neyts J, San-Felix A: Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors. Eur. J. Med. Chem. 2015, 92: 656-671.
  • 13- Strappaghetti G, Brodi C, Giannaccini G, Betti L: New 4-(4-methyl-phenyl) phthalazin-1 (2H)-one derivatives and their effects on α1-receptors. Bioorg. Med. Chem. Lett. 2006, 16: 2575-2579.
  • 14- García ME, Borioni JL, Cavallaro V, Puiatti M, Pierini AB, Murray AP, Peñéñory AB: Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: synthesis, molecular docking and biological studies. Steroids 2015,104: 95-110.
  • 15- Jiang Y, Zhuang C, Chen L, Lu J, Dong G, Miao Z, Zhang W, Li J, Sheng C: Structural biology-inspired discovery of novel KRAS–PDEδ inhibitors. J. Med. Chem. 2017, 60: 9400-9406.
  • 16- He J, Li D, Xiong K, Ge Y, Jin H, Zhang G, Hong M, Tian Y, Yin J, Zeng H: Inhibition of thioredoxin reductase by a novel series of bis-1, 2-benzisoselenazol-3 (2H)-ones: Organoselenium compounds for cancer therapy. Bioorgan. Med. Chem. 2012, 20: 3816-3827.
  • 17- Zhu M, Fang J, Zhang J, Zhang Z, Xie J, Yu Y, Ruan JJ, Chen Z, Hou W, Yang G, Su W, Ruan BH: Biomolecular interaction assays identified dual inhibitors of glutaminase and glutamate dehydrogenase that disrupt mitochondrial function and prevent growth of cancer cells. Anal. Chem. 2017, 89: 1689-1696.
  • 18- Islam MK, Jackson PJM, Thurston DE, Rahman KM: Methylene-linked bis-phenylbenzimidazoles–a new scaffold to target telomeric DNA/RNA hybrid duplex. Org. Biomol. Chem. 2018, 16: 4424-4428.
  • 19- Berger O, Ortial S, Wein S, Denoyelle S, Bressolle F, Durand T, Escale R, Vial HJ, Vo-Hoang Y: Evaluation of amidoxime derivatives as prodrug candidates of potent bis-cationic antimalarials. Bioorg. Med. Chem. Lett. 2019, 29: 2203-2207.
  • 20- Azuma M, Yoshikawa T, Kogure N, Kitajima M, Takayama H: Biogenetically inspired total syntheses of Lycopodium alkaloids, (+)-flabellidine and (−)-lycodine. J. Am. Chem. Soc. 2014, 136: 11618-11621.
  • 21- Bani-Yaseen AD: Solvatochromic and fluorescence behavior of sulfisoxazole. J. Fluoresc. 2011, 21: 1061-1067.
  • 22- Miotke MM, Marek J: Solvatochromism of antiinflammatory drug–naproxen sodium. J. Mol. Liq. 2017, 230: 129-136.
  • 23- Yalcin E, Matković M, Jukić M, Obrovac LG, Piantanida I, Seferoğlu Z: Novel fluorene/fluorenone DNA and RNA binders as efficient non-toxic ds-RNA selective fluorescent probes. Tetrahedron 2018, 74: 535-543.
  • 24- Yalcin E, Erkmen C, Taskin-Tok T, Caglayan MG: Fluorescence chemosensing of meldonium using a cross-reactive sensor array. Analyst, 2020, 145: 3345-3352.
  • 25- Reichardt C: Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 1994, 94: 2319-2358.

Bis-benzamid Türevlerinin Sentezi, Antibakteriyel Aktivitesi ve Fotofiziksel Özellikleri

Yıl 2021, , 143 - 149, 01.09.2021
https://doi.org/10.52794/hujpharm.993718

Öz

Bu çalışmada, 1,12-diaminododekan ve iki farklı açil klorür bileşiğinin reaksiyonu ile N,N'-(dodekan-1,12-diil)bis(2,4-diklorobenzamid) ve N,N'-(dodekan-1,12-diil)bis(4-bromobenzamid) olmak üzere yeni bis-benzamidler sırasıyla %88 ve %92 verimle sentezlendi. Moleküler yapıları 1H NMR, 13C NMR ve FT-IR teknikleri kullanılarak karakterize edildi. Sentezlenen bileşiklerin antibakteriyel aktiviteleri Staphylococcus aureus ATCC 25923 ve Escherichia coli ATCC 25922 suşlarına karşı tarandı. Ayrıca, CH2Cl2 ve CHCl3 içindeki ürünlerin fotofiziksel özellikleri UV-vis spektroskopisi kullanılarak incelendi. Bileşik 3a, çözücü polaritesinin artmasıyla yaklaşık 31 nm'de pozitif solvatokromizm gösterdi.

Proje Numarası

BAP 2020-1-AP5-4097

Kaynakça

  • 1- Wei G, Huang L, Jiang Y, Shen Y, Huang Z, Huang Y, Sun X, Zhao C: Lenvatinib-zinc phthalocyanine conjugates as potential agents for enhancing synergistic therapy of multidrug-resistant cancer by glutathione depletion. Eur. J. Med. Chem. 2019, 169: 53-64.
  • 2- Lopéz-Martínez LM, García-Elías J, Ochoa-Terán A, Ortega HS, Ochoa-Lara K, Montaño-Medina CU, Yatsimirsky AK, Ramírez J, Labastida-Galván V, Ordoñez M: Synthesis, characterization and anion recognition studies of new fluorescent alkyl bis (naphthylureylbenzamide)-based receptors. Tetrahedron 2020, 76: 130815.
  • 3- García-Elías J, Ochoa-Terán A, Yatsimirsky AK, Ortega HS, Ochoa-Lara K, López-Martínez LM, Castro- Riquelme CL, Garcí ÁL, Madrigal-Peralta D, Labastida-Galván V, Ordoñez M: Synthesis and anion recognition studies of new oligomethylene bis (nitrophenylureylbenzamide) receptors. RSC Adv. 2019, 9: 39147-39162.
  • 4- Pina-Luis G, Ochoa-Teran A, Rivero IA: Solid phase synthesis of N-alkyl-bis-o-aminobenzamides for metal ion sensing based on a fluorescent dansyl platform. J. Comb. Chem. 2009, 11: 83-90.
  • 5- Winstanley KJ, Smith DK: Ortho-substituted catechol derivatives: the effect of intramolecular hydrogen-bonding pathways on chloride anion recognition. J. Org. Chem. 2007, 72: 2803-2815.
  • 6- Nguyen M, Meunier B, Robert A: Catechol‐Based Ligands as Potential Metal Chelators Inhibiting Redox Activity in Alzheimer's Disease. Eur. J. Inorg. Chem. 2017, 2017: 3198-3204.
  • 7- Wang J, Hong G, Li G, Wang W, Liu T: Novel homo-bivalent and polyvalent compounds based on ligustrazine and heterocyclic ring as anticancer agents. Molecules 2019, 24: 4505.
  • 8- Filatov AS, Knyazev NA, Shmakov SV, Bogdanov AA, Ryazantsev MN, Shtyrov AA, Starova GL, Malchanov AP, Larina AG, Boitsov VM, Stepakov AV: Concise synthesis of tryptanthrin spiro analogues with in vitro antitumor activity based on one-pot, three-component 1,3-dipolar cycloaddition of azomethine ylides to сyclopropenes. Synthesis 2019, 51: 713-729.
  • 9- Dodo K, Minato T, Hashimoto Y: Structure–activity relationship of bis-galloyl derivatives related to (−)-epigallocatechin gallate. Chemical and Pharmaceutical Bulletin 2009, 57: 190-194.
  • 10- Nguyen TX, Morrell A, Conda-Sheridan M, Marchand C, Agama K, Bermingam A, Stephen AG, Chergui A, Naumova A, Fisher R, O’Keefe BR, Pommier Y, Cushman M: Synthesis and biological evaluation of the first dual tyrosyl-DNA phosphodiesterase I (Tdp1)–topoisomerase I (Top1) inhibitors. J. Med. Chem. 2012, 55: 4457-4478.
  • 11- Al-Masoudi NA, Al-Haidery N, Faili NT, Pannecouque C: Amino acid derivatives. Part 5. Synthesis and anti-HIV activity of new sebacoyl precursor derived thioureido-amino acid and phthalimide derivatives. Arkivoc 2010, 2010: 185-195.
  • 12- Rivero-Buceta E, Carrero P, Doyagüez EG, Madrona A, Quesada E, Camarasa MJ, Pérez- Pérez MJ, Leyssen P, Paeshuyse J, Balzarini J, Neyts J, San-Felix A: Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors. Eur. J. Med. Chem. 2015, 92: 656-671.
  • 13- Strappaghetti G, Brodi C, Giannaccini G, Betti L: New 4-(4-methyl-phenyl) phthalazin-1 (2H)-one derivatives and their effects on α1-receptors. Bioorg. Med. Chem. Lett. 2006, 16: 2575-2579.
  • 14- García ME, Borioni JL, Cavallaro V, Puiatti M, Pierini AB, Murray AP, Peñéñory AB: Solanocapsine derivatives as potential inhibitors of acetylcholinesterase: synthesis, molecular docking and biological studies. Steroids 2015,104: 95-110.
  • 15- Jiang Y, Zhuang C, Chen L, Lu J, Dong G, Miao Z, Zhang W, Li J, Sheng C: Structural biology-inspired discovery of novel KRAS–PDEδ inhibitors. J. Med. Chem. 2017, 60: 9400-9406.
  • 16- He J, Li D, Xiong K, Ge Y, Jin H, Zhang G, Hong M, Tian Y, Yin J, Zeng H: Inhibition of thioredoxin reductase by a novel series of bis-1, 2-benzisoselenazol-3 (2H)-ones: Organoselenium compounds for cancer therapy. Bioorgan. Med. Chem. 2012, 20: 3816-3827.
  • 17- Zhu M, Fang J, Zhang J, Zhang Z, Xie J, Yu Y, Ruan JJ, Chen Z, Hou W, Yang G, Su W, Ruan BH: Biomolecular interaction assays identified dual inhibitors of glutaminase and glutamate dehydrogenase that disrupt mitochondrial function and prevent growth of cancer cells. Anal. Chem. 2017, 89: 1689-1696.
  • 18- Islam MK, Jackson PJM, Thurston DE, Rahman KM: Methylene-linked bis-phenylbenzimidazoles–a new scaffold to target telomeric DNA/RNA hybrid duplex. Org. Biomol. Chem. 2018, 16: 4424-4428.
  • 19- Berger O, Ortial S, Wein S, Denoyelle S, Bressolle F, Durand T, Escale R, Vial HJ, Vo-Hoang Y: Evaluation of amidoxime derivatives as prodrug candidates of potent bis-cationic antimalarials. Bioorg. Med. Chem. Lett. 2019, 29: 2203-2207.
  • 20- Azuma M, Yoshikawa T, Kogure N, Kitajima M, Takayama H: Biogenetically inspired total syntheses of Lycopodium alkaloids, (+)-flabellidine and (−)-lycodine. J. Am. Chem. Soc. 2014, 136: 11618-11621.
  • 21- Bani-Yaseen AD: Solvatochromic and fluorescence behavior of sulfisoxazole. J. Fluoresc. 2011, 21: 1061-1067.
  • 22- Miotke MM, Marek J: Solvatochromism of antiinflammatory drug–naproxen sodium. J. Mol. Liq. 2017, 230: 129-136.
  • 23- Yalcin E, Matković M, Jukić M, Obrovac LG, Piantanida I, Seferoğlu Z: Novel fluorene/fluorenone DNA and RNA binders as efficient non-toxic ds-RNA selective fluorescent probes. Tetrahedron 2018, 74: 535-543.
  • 24- Yalcin E, Erkmen C, Taskin-Tok T, Caglayan MG: Fluorescence chemosensing of meldonium using a cross-reactive sensor array. Analyst, 2020, 145: 3345-3352.
  • 25- Reichardt C: Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 1994, 94: 2319-2358.
Toplam 25 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık ve İlaç Bilimleri
Bölüm Research Articles
Yazarlar

Günseli Bobuş Alkaya 0000-0003-1732-9163

Çağla Efeoğlu

İrem Acar

Ergin Yalçın

Fadime Nazlı Dincer Kaya

Yahya Nural 0000-0002-5986-8248

Proje Numarası BAP 2020-1-AP5-4097
Yayımlanma Tarihi 1 Eylül 2021
Kabul Tarihi 15 Ekim 2021
Yayımlandığı Sayı Yıl 2021

Kaynak Göster

Vancouver Bobuş Alkaya G, Efeoğlu Ç, Acar İ, Yalçın E, Dincer Kaya FN, Nural Y. Synthesis, Antibacterial Activity and Photophysical Properties of Bis-benzamide derivatives. HUJPHARM. 2021;41(3):143-9.