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

Year 2021, , 143 - 149, 01.09.2021

Günseli Bobuş Alkaya , Çağla Efeoğlu , İrem Acar , Ergin Yalçın , Fadime Nazlı Dincer Kaya , Yahya Nural

https://doi.org/10.52794/hujpharm.993718

Abstract

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.

Keywords

Antibacterial activity, Bis-benzamide, Photophysical property

Supporting Institution

Mersin University Research Fund

Project Number

BAP 2020-1-AP5-4097

Thanks

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

Bis-benzamid Türevlerinin Sentezi, Antibakteriyel Aktivitesi ve Fotofiziksel Özellikleri

Abstract

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.

Keywords

Antibakteriyel aktivite, Bis-benzamid, Fotofiziksel özellik

Project Number

BAP 2020-1-AP5-4097

References

• 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.