Synthesis, characterization, antibacterial and antifungal evaluation of novel cyclohexanone benzoylhydrazones

Year 2019, Volume: 49 Issue: 3, 142 - 147, 01.12.2019

Gökçe Cihan-üstündağ , Emel Mataracı-kara Gültaze Çapan

https://izlik.org/JA69FF69JJ

Abstract

A novel series of benzoyl hydrazones (2a-j) were synthesized and evaluated, in vitro, for antimicrobial activity against selected bacteria and fungi. The structures of the compounds were established by IR, 1 H-NMR, 13C-NMR (APT), electrospray ionization mass spectrometry (ESI-MS) and microanalysis (C, H, N). All of the tested compounds, except for compound 2h, displayed weak antibacterial properties against Staphylococcus epidermidis ATCC 12228 and Staphylococcus aureus ATCC 29213. Compounds 2a, 2b, 2e, 2f and 2i further exhibited marginal antifungal activity against Candida parapsilosis

Keywords

Hydrazone , cyclohexanone , antibacterial activity , antifungal activity

References

•  (2018) WHO-World Health Organization. Antibiotic resistance, https://www.who.int/news-room/fact-sheets/detail/antibiotic-resistance. Accessed 05.04.2019.  Backes GL, Neumann DM, Jursic BS (2014) Synthesis and antifungal activity of substituted salicylaldehyde hydrazones, hydrazides and sulfohydrazides. Bioorg Med Chem 22: 4629-36.  Clinical Laboratory Standards Institute (CLSI) document (1997) Approved standard-2nd edition M27-A2. Clinical and Laboratory Standards Institute. Wayne, PA, USA.  Clinical Laboratory Standards Institute (CLSI) document (2006). Approved standard-7th edition M7-A7. Clinical and Laboratory Standards Institute. Wayne, PA, USA.  Ge YQ, Li FR, Zhang YJ, Bi YS, Cao XQ, Duan GY, Wang JW, Liu ZL (2014) Synthesis, crystal structure, optical properties and antibacterial evaluation of novel imidazo[1,5‐a]pyridine derivatives bearing a hydrazone moiety. Luminescence 29: 293-300.  Gürkök G, Altanlar N, Süzen S (2009) Investigation of antimicrobial activities of indole-3-aldehyde hydrazide/hydrazone derivatives. Chemotherapy 55: 15-19.  Kaplancıklı ZA, Yurttas L, Turan-Zitouni G, Özdemir A, Göğer G, Demirci F, Mohsen UA (2014) Synthesis and antimicrobial activity of new pyrimidine-hydrazones. Lett Drug Des Discov 11: 76-81.  Kumar D, Judge V, Narang R, Sangwan S, De Clercq E, Balzarini J, Narasimhan B (2010) Benzylidene/2-chlorobenzylidene hydrazides: Synthesis, antimicrobial activity, QSAR studies and antiviral evaluation. Eur J Med Chem 45: 2806-2816.  Laxminarayan R, Sridhar D, Blaser M, Wang M, Woolhouse M (2016) Achieving global targets for antimicrobial resistance. Science 353: 874-875.  Luepke KH, Suda KJ, Boucher H, Russo RL, Bonney MW, Hunt TD, Mohr (2017) Past, present, and future of antibacterial economics: Increasing bacterial resistance, limited antibiotic pipeline and societal implications. Pharmacotherapy 37: 71-84.  Moldovan C, Oniga O, Meda R, Tiperciuc B, Verite P, Pirnau A, Crisan O, Bojita M (2011) Synthesis and antimicrobial screening of novel 2, 3 or 4-[2-aryl-thiazol-ylmethoxy (oxo-ethoxy)]-benzaldehyde isonicotinoyl hydrazone analogs. Farmacia 59: 659-668.  Morjan RY, Mkadmh AM, Beadham I, Elmanama AA, Mattar MR, Raftery J, Pritchard RG, Awadallah AM, Gardiner JM (2014) Antibacterial activities of novel nicotinic acid hydrazides and their conversion into N-acetyl-1,3,4-oxadiazoles. Bioorg Med Chem Lett 24: 5796-5800.  Nastasa C, Tiperciuc B, Duma M, Benedec D, Oniga O (2015) New hydrazones bearing thiazole scaffold: Synthesis, characterization, antimicrobial, and antioxidant investigation. Molecules 20: 17325-17338.  Niazi S, Javali C, Paramesh M, Shivaraja S (2010) Study of influence of linkers and substitutions on antimicrobial activity of some Schiff bases. Int J Pharm Pharm Sci 2: 108-112.  Pieczonka AM, Strzelczyk A, Sadowska B, Mlostoń G, Stączek P (2013) Synthesis and evaluation of antimicrobial activity of hydrazones derived from 3-oxido-1H-imidazole-4-carbohydrazides. Eur J Med Chem 64: 389-395.  Popiolek L (2017) Hydrazide–hydrazones as potential antimicrobial agents: overview of the literature since 2010. Med Chem Res 26: 287–301.  Sapra A, Kumar P, Kakkar S, Narasimhan B (2014) Synthesis, antimicrobial evaluation and QSAR studies of p-hydroxy benzoic acid derivatives. Drug Res 64: 17-22.  Shlaes DM, Sahm D, Opiela C, Spellberg B (2013) The FDA reboot of antibiotic development. Antimicrob Agents Chemother 57: 4605-4607.  Silverstein RM, Webster FX, Kiemle DJ (2005) Spectrometric identification of organic compounds. 7th ed, John Wiley & Sons, New York.  Sridhar P, Alagumuthu M, Arumugam S, Reddy SR (2016) Synthesis of quinoline acetohydrazide-hydrazone derivatives evaluated as DNA gyrase inhibitors and potent antimicrobial agents. RSC Adv 6: 64460-64468.  Tacconelli E, Carrara E, Savoldi A, Harbarth S, Mendelson M, Monnet DL, Pulcini C, Kahlmeter G, Kluytmans J, Carmeli Y, Ouellette M, Outterson K, Patel J, Cavaleri M, Cox EM, Houchens CR, Grayson ML, Hansen P, Singh N, Theuretzbacher U, Magrini N (2018) Discovery, research, and development of new antibiotics: the WHO priority list of antibiotic-resistant bacteria and tuberculosis. Lancet Infect Dis 18: 318-327.  Tajudeen SS, Kannappan G (2013) Synthetic, structural and pharmacological studies on some isonicotinohydrazide and benzohydrazide analogues. J Pharm Res 7: 534-539.  Tatar E, Şenkardeş S, Sellitepe HE, Küçükgüzel ŞG, Karaoğlu ŞA, Bozdeveci A, De Clercq E, Pannecouque C, Hadda TB, Küçükgüzel İ (2016) Synthesis and prediction of molecular properties and antimicrobial activity of some acylhydrazones derived from N-(arylsulfonyl)methionine. Turk J Chem 40: 510-534.  Vicini P, Zani F, Cozzini P, Doytchinova I (2002) Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem 37: 553-564.  Xavier JJF, Krishnasamy K, Sankar C (2012) Synthesis and antibacterial, antifungal activities of some 2r,4c-diaryl-3-azabicyclo[3.3.1]nonan-9-one-4-aminobenzoyl hydrazones. Med Chem Res 21: 345-350.