Yıl 2018, Cilt 19, Sayı 1, Sayfalar 43 - 49 2018-03-31

NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES

Hakan ÜNVER [1] , Zerrin CANTURK [2]

151 177

Thiophene belongs to a class of heterocyclic compounds. In this study, three new dimethyl-5-hydroxy isophtalate derived thiophene esters were successfully synthesized and characterized by FT-IR, elemental analysis, 1H-NMR, 13C-NMR and HR-Mass techniques. Synthesized compounds antimicrobial effects were tested on Staphylococcus aureus (ATCC 25923); Enterococcus faecalis  (ATCC 29212); Enterococcus faecalis (ATCC 51922); Klebsiella pneumoniae (ATCC 700603); Pseudomonas aeruginosa (ATCC 27853); Escherichia coli (ATCC 35218); Escherichia coli (ATCC 25922) and Candida albicans (ATCC 90028); Candida glabrata (ATCC 90030); Candida krusei (ATCC 6258); Candida parapsilosis (ATCC 22019). Compound C1 showed the highest antimicrobial activity, possessing the same potential as chloramphenicol against, P. aeruginosa ATCC 27853. According to MTT assays, this compound was identified as non-toxic.

Thiophene, Antibacterial, Anticandidal, MIC, Ketokanazole
  • [1] Martinez, J. L.; Baquero, F.; Andersson, D. I. Predicting Antibiotic Resistance, Nature Reviews Microbiology, 2007, 5, 958−965.
  • [2] Zhang, Q. C.; Lambert, G.; Liao, D.; Kim, H.; Robin, K.; Tung, C. K.; Pourmand, N.; Austin, R. H. Acceleration of Emergence of Bacterial Antibiotic Resistance in Connected Microenvironments, Science, 2011, 333, 1764−1767.
  • [3] Høiby, N.; Bjarnsholt, T.; Givskov, M.; Molinc, S.; Ciofu, O., Antibiotic resistance of bacterial biofilms, International Journal of Antimicrobial Agents, 2010, 35, 322–332.
  • [4] Andersson, D. I.; Hughes, D., Microbiological effects of sublethal levels of antibiotics, Nature Reviews Microbiology, 2014, 8, 260-271.
  • [5] Jo, Y. W.; Im, W. B.; Rhee, J. K.; Shim, M. J.; Kimb, W. B. and Choi, E. C., Synthesis and antibacterial activity of oxazolidinones containing pyridine substituted with heteroaromatic ring, Bioorganic & Medicinal Chemistry, 2004, 12, 5909–5915.
  • [6] Raja, R.; Sivasubramaniyan, A.; Murugan, D.; Subbaiah, N.; George, J.; Poovan, S.; Sangaraiah, N.; Alagusundaram, P; Shanmugam, K.; Manivachagam, C. A green synthesis of 1,2,3-triazolyl-pyridine hybrids and evaluation of their antibacterial activity, Res. Chem. Intermed., 2016, 42, 8005–8021.
  • [7] Elagamey, A. G.; Sattar, S. A; Taweel, F. E. and Said, S. An Efficient Synthesis and Antibacterial Activity of Pyrido[2,3-d] Pyrimidine, Chromeno[3,4-c]Pyridine, Pyridine, Pyrimido[2,3-c] Pyridazine, Enediamines, and Pyridazine Derivatives, J. Heterocyclic Chem., 2016, 53, 1801.
  • [8] Baharfar, R.; Asghari, S.; Rassi, S; Mohseni, M., Synthesis and evaluation of novel isatin and 5-isatinylidenerhodanine-based furan derivatives as antibacterial agents, Res. Chem. Intermed., 2015, 41, 6975–6984.
  • [9] Rani, M.; Yusuf, M.; Khan, S. A., Synthesis and in-vitro-antibacterial activity of [5-(furan-2-yl)-phenyl]-4,5-carbothioamide-pyrazolines, Journal of Saudi Chemical Society, 2012, 16, 431–436.
  • [10] Jin, Y. X.; Zhong, A. G.; Ge, C. H.; Pan, F. Y.; Yang, J. G.; Wu, Y.; Xie, M.; Feng, H. W., A novel difunctional acylhydrazone with isoxazole and furan heterocycles: Syntheses, structure, spectroscopic properties, antibacterial activities and theoretical studies of (E)-N’-(furan-2-ylmethylene)-5-methylisoxazole-4-carbohydrazide, Journal of Molecular Structure, 2012, 1010, 190–196.
  • [11] Balachandra, B.; Shanmugam, S.; Muneeswaran, T.and Ramakritinan, M., Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agents, RSC Adv., 2015, 5, 64781.
  • [12] Joshi, S. D.; More Y.; Vagdevi, H. M.; Vaidya, V. P.; Gadaginamath, G. S.; Kulkarni, V. H., Synthesis of new 4-(2,5-dimethylpyrrol-1-yl)/4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyrrole ring systems: a novel class of potential antibacterial, antifungal and antitubercular agents, Med. Chem. Res., 2013, 22, 1073–1089.
  • [13] Kaping, S.; Boiss, I.; Singha, L. I.; Helissey, P.; Vishwakarma, J. N., A facile, regioselective synthesis of novel 3-(N- phenylcarboxamide)pyrazolo[1,5-a]pyrimidine analogs in the presence of KHSO4 in aqueous media assisted by ultrasound and their antibacterial activities, Mol. Divers., 2016, 20, 379–390.
  • [14] Verbitskiy, E. V.; Baskakova, S. A.; Rasputin, N. A.; Gerasimova, N. A.; Amineva, P. G.; Evstigneeva, N. P.; Zil’berberg, N. V.; Kungurov, N. V.; Kravchenko, M. A.; Skornyakov, S. N.; Rusinov, G. L.; Chupakhin, O. N. and Charushin, V. N., Microwave-assisted synthesis and evaluation of antibacterial activity of novel 6-fluoroaryl-[1,2,4]triazolo[1,5-a]pyrimidines, ARKIVOC, 2016, 5, 268-278.
  • [15] Mabkhot, Y. N.; Kaal, N. A.; Alterary, S.; Showiman, S; Barakat, A.; Ghabbour, H. A. and Frey, W., Molecules, 2015, 20, 8712-8729.
  • [16] Kaya, E.; Turan, N.; Gündüz, B.; Çolak, N.; Körkoca, H., Synthesis, Characterization of Poly-2- (2-hydroxybenzylideneamino)-6-phenyl-4,5,6, 7-tetrahydrobenzo[b]thiophene-3-carbonitrile: Investigation of Antibacterial Activity and Optical Properties, Polymer Engineering And Science, 2012, 52, 7, 1581-1589.
  • [17] Elsabee, M. Z.; Ali, E. A.; Mokhtar, S. M.; Eweis, M., Synthesis, characterization polymerization and antibacterial properties of novel thiophene substituted acrylamide, Reactive & Functional Polymers, 2011, 71, 1187–1194.
  • [18] Wardakhan, W. W.; Louca, N. A. and Kamel, M. M, The Reaction of 2-Aminocyclohexeno[b]thiophene Derivatives with Ethoxycarbonyl isothiocyanate: Synthesis of Fused Thiophene Derivatives with Antibacterial and Antifungal Activities, Acta Chim. Slov., 2007, 229, 54, 229–241.
  • [19] Zhao, Q.; Li, J.; Zhang, X.; Li, Z. and Tang, Y., Cationic Oligo(thiophene ethynylene) with Broad-Spectrum and High Antibacterial Efficiency under White Light and Specific Biocidal Activity against S. aureus in Dark, ACS Appl. Mater. Interfaces, 2016, 8, 1019−1024.
  • [20] Patel, S.; Gheewala, N.; Suthar, A.; Shah, A. In-vitro cytotoxicity activity of Solanum nigrum extract against Hela cell line and Vero cell line. Int. J. Pharm. Pharm. Sci., 2009, 1(1), 38-46.
  • [21] Protopopova, M.; Hanrahan, C.; Nikonenko, B.; Samala, R.; Chen, P.; Gearhart, J.; Einck L.; Nacy, C.A. Identification of a new antitubercular drug candidate, SQ109, from a combinatorial library of 1,2-ethylenediamines. J. Antimicrob. Chemother., 2005, 56(5), 968-974.
  • [22] Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically Approved Standard; Wayne, PA, USA, 2006.
  • [23] Eweis, M.; Elkholy, S.; Elsabee, M. S.; Antifungal efficacy of chitosan and its thiourea derivatives upon the growth of some sugar-beet pathogens, Int. J. Biol. Macromol., 2006, 38, 1–8.
  • [24] Gündüzalp, A. B.; Özbek, N. and Karacan, N., Synthesis, characterization, and antibacterial activity of the ligands including thiophene/furan ring systems and their Cu(II), Zn(II) complexes, Med Chem Res, 2012, 21, 3435–3444.
Konular Mühendislik ve Temel Bilimler
Dergi Bölümü Araştırma Makalesi
Yazarlar

Yazar: Hakan ÜNVER
Kurum: Anadolu University
Ülke: Turkey


Yazar: Zerrin CANTURK
Kurum: Anadolu University
Ülke: Turkey


Bibtex @araştırma makalesi { aubtda335519, journal = {Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi A - Uygulamalı Bilimler ve Mühendislik}, issn = {1302-3160}, eissn = {2146-0205}, address = {Anadolu Üniversitesi}, year = {2018}, volume = {19}, pages = {43 - 49}, doi = {10.18038/aubtda.335519}, title = {NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES}, key = {cite}, author = {CANTURK, Zerrin and ÜNVER, Hakan} }
APA ÜNVER, H , CANTURK, Z . (2018). NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES. Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi A - Uygulamalı Bilimler ve Mühendislik, 19 (1), 43-49. DOI: 10.18038/aubtda.335519
MLA ÜNVER, H , CANTURK, Z . "NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES". Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi A - Uygulamalı Bilimler ve Mühendislik 19 (2018): 43-49 <http://dergipark.gov.tr/aubtda/issue/36292/335519>
Chicago ÜNVER, H , CANTURK, Z . "NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES". Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi A - Uygulamalı Bilimler ve Mühendislik 19 (2018): 43-49
RIS TY - JOUR T1 - NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES AU - Hakan ÜNVER , Zerrin CANTURK Y1 - 2018 PY - 2018 N1 - doi: 10.18038/aubtda.335519 DO - 10.18038/aubtda.335519 T2 - Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi A - Uygulamalı Bilimler ve Mühendislik JF - Journal JO - JOR SP - 43 EP - 49 VL - 19 IS - 1 SN - 1302-3160-2146-0205 M3 - doi: 10.18038/aubtda.335519 UR - http://dx.doi.org/10.18038/aubtda.335519 Y2 - 2017 ER -
EndNote %0 Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi A - Uygulamalı Bilimler ve Mühendislik NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES %A Hakan ÜNVER , Zerrin CANTURK %T NEW THIOPHENE BEARING DIMETHYL-5-HYDROXY ISOPHTALATE ESTERS AND THEIR ANTIMICROBIAL ACTIVITIES %D 2018 %J Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi A - Uygulamalı Bilimler ve Mühendislik %P 1302-3160-2146-0205 %V 19 %N 1 %R doi: 10.18038/aubtda.335519 %U 10.18038/aubtda.335519