Yıl: 2021 Cilt: 25 Sayı: 2 Sayfa Aralığı: 135 - 141 Metin Dili: İngilizce DOI: 10.29228/jrp.4 İndeks Tarihi: 31-05-2021

Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents

Öz:
In this study, some N′‑(substituted arylmethylidene)-4‑nitrobenzenesulfonohydrazide derivatives were synthesis by reacting various aldehydes and 4‑nitrobenzenesulfonohydrazide. The structural characterization of the compounds was performed byIR, 1H-NMR and TOF-MS(compounds 3b and 3e) spectroscopic data besides elementel analyses results. The antibacterial activities of these compounds wereexamined against some bacteria species. The compounds showed the highest activity against Pseudomonas aeruginosaATCC 27853. Also, anti-quorum sensing activities have been determined using a biosensor bioassay with Chromobacterium violaceumCV026 and the signaling molecule N-hexanoyl-L-homoserine lactone. All the compounds were subjected for ADME predictions by computational method.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • [1] Tagliabue A, Rappuoli R. Changing priorities in vaccinology: Antibiotic resistance moving to the top. Front Immunol. 2018; 9: 1068. [CrossRef]
  • [2] Papenfort K, Bassler BL. Quorum sensing signal-response systems in Gram-negative bacteria. Nat Rev Microbiol. 2016; 14(9): 576–588. [CrossRef]
  • [3] Sakuragi Y, Kolter R. Quorum-sensing regulation of the biofilm matrix genes (pel) of Pseudomonas aeruginosa. J Bacteriol. 2007; 189(14): 5383–5386. [CrossRef]
  • [4] McClean KH, Winson MK, Fish L, Taylor A, Chhabra SR, Camara M, Daykin M, Lamb JH, Swift S, Bycroft BW, Stewart GS, Williams P. Quorum sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology. 1997; 143(12): 3703–3711. [CrossRef]
  • [5] Rafiee F, Haghi F, Bikas R, Heidari A, Gholami M, Kozakiewicz A, Zeighami H. Synthesis, characterization and assessment of anti-quorum sensing activity of copper(II)-ciprofloxacin complex against Pseudomonas aeruginosa PAO1. AMB Express. 2020; 10(1): 82. [CrossRef]
  • [6] Aminov RI. A brief history of the antibiotic era: Lessons learned and challenges for the future. Front Microbiol. 2010; 1: 134. [CrossRef]
  • [7] Fair RJ, Tor Y. Antibiotics and bacterial resistance in the 21st century. Perspect Medicin Chem. 2014; 6: 25–64. [CrossRef]
  • [8] De Oliveira KN, Costa P, Santin JR, Mazzambani L, Bürger C, Mora C, Nunes RJ, Souza MM. Synthesis and antidepressant-like activity evaluation of sulphonamides and sulphonyl-hydrazones. Bioorganic Med Chem. 2011; 19(14): 4295–4306. [CrossRef]
  • [9] Karaman N, Oruç-Emre EE, Sıcak Y, Çatıkkaş B, Karaküçük-İyidoğan A, Öztürk M. Microwave-assisted synthesis of new sulfonyl hydrazones, screening of biological activities and investigation of structure–activity relationship. Med Chem Res. 2016; 25(8): 1590–1607. [CrossRef]
  • [10] Şenkardeş S, Han Mİ, Kulabaş N, Abbak M, Çevik Ö, Küçükgüzel İ, Küçükgüzel ŞG. Synthesis, molecular docking and evaluation of novel sulfonyl hydrazones as anticancer agents and COX-2 inhibitors. Mol Divers. 2020; 24(3): 673– 689. [CrossRef]
  • [11] Özmen Özdemir Ü, Altuntaş A, Gündüzalp AB, Arslan F, Hamurcu F. New aromatic/heteroaromatic propanesulfonylhydrazone compounds: Synthesis, physical properties and inhibition studies against carbonic anhydrase II (CAII) enzyme. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2014; 128: 452–460. [CrossRef]
  • [12] Gündüzalp AB, Parlakgümüş G, Uzun D, Özmen ÜÖ, Özbek N, Sarı M, Tunç T. Carbonic anhydrase inhibitors: Synthesis, characterization and inhibition activities of furan sulfonylhydrazones against carbonic anhydrase I (hCA I). J Mol Struct. 2016; 1105: 332–340. [CrossRef]
  • [13] Aslan HG, Karacan N. Aromatic sulfonyl hydrazides and sulfonyl hydrazones: Antimicrobial activity and physical properties. Med Chem Res. 2013; 22(3): 1330–1338. [CrossRef]
  • [14] Dodoff NI, Özdemir Ü, Karacan N, Georgieva MC, Konstantinov SM, Stefanova ME. Schiff Bases of Methanesulfonylhydrazine. Synthesis, Spectroscopic Characterization, Conformational Analysis, and Biological Activity. Z Naturforsch B. 1999; 54(12): 1553–1562. [CrossRef]
  • [15] Muhammad YA, Narang R, Nayak SK, Singh SK. Synthesis, antibacterial activity and molecular docking studies of N’-benzylidene/N’-(1-phenylethylidene)hexa-2,4-dienehydrazide derivatives. J Chem Pharm Res. 2016; 8(3): 930- 937.
  • [16] Nastasa C, Tiperciuc B, Duma M, Benedec D, Oniga O. New hydrazones bearing thiazole scaffold: Synthesis, characterization, antimicrobial, and antioxidant investigation. Molecules. 2015; 20(9): 17325–17338. [CrossRef]
  • [17] Ibrahim HM, Behbehani H, Elnagdi MH. Approaches towards the synthesis of a novel class of 2-amino-5- arylazonicotinate, pyridazinone and pyrido[2,3-d]pyrimidine derivatives as potent antimicrobial agents. Chem Cent J. 2013; 7(1): 1–16. [CrossRef]
  • [18] Fernandes TB, Cunha MR, Sakata RP, Candido TM, Baby AR, Tavares MT, et al. Synthesis, molecular modeling, and evaluation of novel sulfonylhydrazones as acetylcholinesterase inhibitors for Alzheimer’s disease. Arch Pharm (Weinheim). 2017; 350(11): 1–16. [CrossRef]
  • [19] Younus HA, Hameed A, Mahmood A, Khan MS, Saeed M, Batool F, Asair A, Mohamad H, Pelletier J, Sevigny J, Iqbal J, al-Rashida M. Sulfonylhydrazones: Design, synthesis and investigation of ectonucleotidase (ALP&e5’NT) inhibition activities. Bioorg Chem. 2020; 100: 103827. [CrossRef]
  • [20] Tacic A, Nikolic V, Nikolic L, Savic I. Antimicrobial sulfonamide drugs. Adv Technol. 2017;6(1):58–71.
  • [21] Daina A, Michielin O, Zoete V. SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017; 7: 42717. [CrossRef]
  • [22] Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 2012; 64(SUPPL.): 4–17. [CrossRef]
  • [23] Zhao YH, Abraham MH, Le J, Hersey A, Luscombe CN, Beck G, Sherborne B, Cooper I. Rate-limited steps of human oral absorption and QSAR studies. Pharm Res. 2002; 19(10): 1446–1457. [CrossRef]
  • [24] ISO 20776-1 (2006). Clinical laboratory testing and in vitro diagnostic test systems - Susceptibility testing of infectious agents and evaluation of performance of antimicrobial susceptibility test devices -Part 1: Reference method for testing the in vitro activity of antimicrobial agents against rapidly growing aerobic bacteria involved in infectious diseases.
  • [25] The European Committee on Antimicrobial Susceptibility Testing (EUCAST). Routine and extended internal quality control for MIC determination and disk diffusion as recommended by EUCAST. Version 8.0, 2018.
  • [26] Erdönmez D, Rad AY, Aksöz N. Anti-Quorum sensing potential of antioxidant quercetin and resveratrol. Brazilian Arch Biol Technol. 2018; 61: 18160756. [CrossRef]
APA şenkardeş s, Kiymaci M, KALE K, Kozanoğlu İ, Kaskatepe B, Küçükgüzel Ş (2021). Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. , 135 - 141. 10.29228/jrp.4
Chicago şenkardeş sevil,Kiymaci Merve Eylul,KALE Kübra,Kozanoğlu İsa Murat,Kaskatepe Banu,Küçükgüzel Ş.Güniz Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. (2021): 135 - 141. 10.29228/jrp.4
MLA şenkardeş sevil,Kiymaci Merve Eylul,KALE Kübra,Kozanoğlu İsa Murat,Kaskatepe Banu,Küçükgüzel Ş.Güniz Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. , 2021, ss.135 - 141. 10.29228/jrp.4
AMA şenkardeş s,Kiymaci M,KALE K,Kozanoğlu İ,Kaskatepe B,Küçükgüzel Ş Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. . 2021; 135 - 141. 10.29228/jrp.4
Vancouver şenkardeş s,Kiymaci M,KALE K,Kozanoğlu İ,Kaskatepe B,Küçükgüzel Ş Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. . 2021; 135 - 141. 10.29228/jrp.4
IEEE şenkardeş s,Kiymaci M,KALE K,Kozanoğlu İ,Kaskatepe B,Küçükgüzel Ş "Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents." , ss.135 - 141, 2021. 10.29228/jrp.4
ISNAD şenkardeş, sevil vd. "Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents". (2021), 135-141. https://doi.org/10.29228/jrp.4
APA şenkardeş s, Kiymaci M, KALE K, Kozanoğlu İ, Kaskatepe B, Küçükgüzel Ş (2021). Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. Journal of research in pharmacy (online), 25(2), 135 - 141. 10.29228/jrp.4
Chicago şenkardeş sevil,Kiymaci Merve Eylul,KALE Kübra,Kozanoğlu İsa Murat,Kaskatepe Banu,Küçükgüzel Ş.Güniz Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. Journal of research in pharmacy (online) 25, no.2 (2021): 135 - 141. 10.29228/jrp.4
MLA şenkardeş sevil,Kiymaci Merve Eylul,KALE Kübra,Kozanoğlu İsa Murat,Kaskatepe Banu,Küçükgüzel Ş.Güniz Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. Journal of research in pharmacy (online), vol.25, no.2, 2021, ss.135 - 141. 10.29228/jrp.4
AMA şenkardeş s,Kiymaci M,KALE K,Kozanoğlu İ,Kaskatepe B,Küçükgüzel Ş Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. Journal of research in pharmacy (online). 2021; 25(2): 135 - 141. 10.29228/jrp.4
Vancouver şenkardeş s,Kiymaci M,KALE K,Kozanoğlu İ,Kaskatepe B,Küçükgüzel Ş Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents. Journal of research in pharmacy (online). 2021; 25(2): 135 - 141. 10.29228/jrp.4
IEEE şenkardeş s,Kiymaci M,KALE K,Kozanoğlu İ,Kaskatepe B,Küçükgüzel Ş "Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents." Journal of research in pharmacy (online), 25, ss.135 - 141, 2021. 10.29228/jrp.4
ISNAD şenkardeş, sevil vd. "Synthesis, structural elucidation and biological activities of some novel sulfonyl hydrazones as antibacterial agents". Journal of research in pharmacy (online) 25/2 (2021), 135-141. https://doi.org/10.29228/jrp.4