Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives

Özlem Akgül; İsmail Öztürk; Abdurrahman Aygül; Şafak Ermertcan

doi:10.12991/marupj.300894

Araştırma Makalesi

Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives

Yıl 2017, Cilt: 21 Sayı: 2, 361 - 370, 01.04.2017

Özlem Akgül İsmail Öztürk Abdurrahman Aygül Şafak Ermertcan

https://doi.org/10.12991/marupj.300894

Öz

In this study, a series of taurinamide derivatives were synthesized

and screened for their antimicrobial activity. The structures of

the newly synthesized compounds 11-15 were evaluated by

1H NMR, IR, MS-APCI and elemental analysis. Compounds

(1-15) were tested against standard strains of Gram(+),

Gram(−) bacteria and fungi by using disc diffusion and broth

microdilution methods. Although disc diffusion method did

not show any comparable results due to the solubility properties

of the compounds; microdilution method results indicated that

title compounds showed from poor to good activity against

only Enterococcus faecalis. It can be concluded that phtalimido

moiety, secondary aryl sulphonamide group and electrondonating

group substitution on phenyl ring are essential for

the antibacterial activity. Among the tested compounds, para

substituted methyl and methoxy derivatives of N-phenyl-2-

phthalimidotaurinamide (4, 7), displayed equipotent activity

compared to standard drug gentamicin.

Anahtar Kelimeler

Taurinamide, N-substituted-2- phtalimidoethanesulfonamide, antibacterial, Enterococcus faecalis, microdilution

Kaynakça

1. Docquier JD, Cusi MG. Editorial overview: Anti-infectives:Towards novel antiviral and antibacterial drugs? Currentapproaches to address a growing medical need. Curr OpinPharmacol 2014; 18: iv–vi.
2. Davis DC, Mohammad H, Kyei-Baffour K, Younis W, CreemerCN, Seleem MN, Dai, M. Discovery and characterization ofaryl isonitriles as a new class of compounds versus methicillinandvancomycin-resistant Staphylococcus aureus. Eur J MedChem 2015; 101: 384–90.
3. Qin W, Panunzio M, Biondi S. β-Lactam AntibioticsRenaissance. Antibiotics 2014; 3: 193–215.
4. Walsh CT, Wencewicz TA. Prospects for new antibiotics: amolecule-centered perspective. J Antibiot 2014; 67: 7–22.
5. Elumalai K, Ali MA, Elumalai M, Eluri K, Srinivasan S,Sivannan S, Mohanthi SK. Synthesis, characterization andbiological evaluation of acetazolamide, cycloserine andisoniazid condensed some novel phthalimide derivatives. IntJ Chem Anal Sci 2013; 4: 57–61.
6. Orzeszko A, Kamińska B, Starościak BJ. Synthesis andantimicrobial activity of new adamantane derivatives III.Farmaco 2002; 57: 619–24.
7. Sachan D, Singh JP, Sachan D, Gangwar S. Design, synthesisand antimicrobial evaluation of mannich bases of novelisoindole analogues. Am J PharmTech Res 2012;2: 491-7.
8. Kamiński K, Obniska J, Wiklik B, Atamanyuk D. Synthesisand anticonvulsant properties of new acetamide derivativesof phthalimide, and its saturated cyclohexane and norborneneanalogs. Eur J Med Chem 2011; 46: 4634–41.
9. Santos JL, Yamasaki PR, Chin CM, Takashi CH, PavanFR, Leite CQF. Synthesis and in vitro anti Mycobacteriumtuberculosis activity of a series of phthalimide derivatives.Bioorg Med Chem 2009; 17: 3795–9.
10. Yang YJ, Yang YN, Jiang JS, Feng ZM, Liu HY, Pan XD, Zhang,PC. Synthesis and cytotoxic activity of heterocycle-substitutedphthalimide derivatives. Chin Chem Lett 2010; 21: 902–4.
11. Lima LM, Castro P, Machado AL, Fraga CAM, Lugnier C, DeMoraes VLG, Barreiro, EJ. Synthesis and anti-inflammatoryactivity of phthalimide derivatives, designed as newthalidomide analogues. Bioorg Med Chem 2002; 10: 3067–73.
12. Winterbottom R, Clapp JW, Miller WH, English JP, RoblinRO. Studies in chemotherapy. XV. Amides of pantoyltaurine 1.J Am Chem Soc 1947; 69: 1393–1401.
13. Smits RA, Adami M, Istyastono EP, Zuiderveld OP, van DamCME, de Kanter FJJ, Jongejan A, Coruzzi G, Leurs R, de EschIJP. Synthesis and QSAR of quinazoline sulfonamides ashighly potent human histamine H4 receptor inverse agonists.J Med Chem 2010; 53: 2390–2400.
14. Chung MC, Malatesta P, Bosquesi PL, Yamasaki PR, dosSantos JL, Vizioli EO. Advances in drug design based on theamino acid approach: Taurine analogues for the treatment ofCNS diseases. Pharmaceuticals 2012; 5: 1128–46.
15. Sharma R, Soman SS. Design and synthesis of sulfonamidederivatives of pyrrolidine and piperidine as anti-diabeticagents. Eur J Med Chem 2015; 90: 342–50.
16. Capasso C, Supuran CT. Anti-infective carbonic anhydraseinhibitors: A patent and literature review. Expert Opin TherPat 2013; 23: 693–704.
17. Supuran CT, Casini A, Scozzafava A. Protease inhibitors of thesulfonamide type: Anticancer, antiinflammatory, and antiviralagents. Med Res Rev 2003; 23: 535–58.
18. Kumar M, Ramasamy K, Mani V, Mishra RK, MajeedABA, Clercq ED, Narasimhan, B. Synthesis, antimicrobial,anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substitutedbenzene sulfonamides. Arab J Chem 2014; 7: 396–408.
19. Chohan ZH, Youssoufi MH, Jarrahpour A, Ben Hadda T.Identification of antibacterial and antifungal pharmacophoresites for potent bacteria and fungi inhibition: Indolenylsulfonamide derivatives. Eur J Med Chem 2010; 45: 1189–99.
20. Zani F, Vicini P, Incerti M. Synthesis and antimicrobialproperties of 2-(benzylidene-amino)benzo[d]isothiazol-3-ones. Eur J Med Chem 2004; 39: 135–40.
21. Jarrahpour A, Shirvani P, Sharghi H, Aberi M, Sinou V,Latour C, Brunel J. Synthesis of novel mono- and bis-Schiffbases of morpholine derivatives and the investigation of theirantimalarial and antiproliferative activities. Med Chem Res2015; 24: 4105–12.
22. Oliveira MTA, Teixeira AMR, Cassiano CJM, Sena DM,Coutinho HDM, Menezes IRA, Figueredo FG, Silva LE, ToledoTA, Bento RR.F. Modulation of the antibiotic activity againstmultidrug resistant strains of 4-(phenylsulfonyl) morpholine.Saudi J Biol Sci 2016; 23: 34–8.
23. Akgul O, Sultan Kılıc F, Erol K, Pabuccuoglu V. Synthesisand anticonvulsant activity of some N-Phenyl-2-phtalimidoethanesulfonamide derivatives. Arch Pharm(Weinheim) 2007; 340: 656–60.
24. Romanowski EG, Yates KA, Teuchner B, Nagl M, Irschick EU,Gordon YJ. N-Chlorotaurine is an effective antiviral agentagainst adenovirus in vitro and in the Ad5/NZW rabbit ocularmodel. Invest Ophthalmol Vis Sci 2006; 47: 2021–6.
25. Corte DL, Crichton, RR, Duburs G, Nolan K, Tipton KF,Tirzitis G, Ward RJ. The use of taurine analogues to investigatetaurine functions and their potential therapeutic applications.Amino Acids 2002; 23: 367–79.
26. Curley OMS, McCormick JE, McElhinney RS, McMurryTBH. Intermediates in the Ing Manske reaction. Arkivoc 2003;7: 180–9.
27. Jorgensen JH, Ferraro MJ. Antimicrobial susceptibility testing:A review of general principles and contemporary practices.Clin Infect Dis 2009; 49: 1749–55.
28. Bielenica A, Stefanska J, Stepien K, Napiorkowska A,Augustynowicz-Kopec E, Sanna G, Madeddu, S, Boi S,Giliberti G, Wrzosek M, Struga M. Synthesis, cytotoxicity andantimicrobial activity of thiourea derivatives incorporating3-(trifluoromethyl)phenyl moiety. Eur J Med Chem 2015; 101:111–25.
29. De Almeida CG, Garbois GD, Amaral LM, Diniz CC, LeHyaric M. Relationship between structure and antibacterialactivity of lipophilic N-acyldiamines. Biomed Pharmacother2010; 64: 287–90.
30. Koktaş Koca S, Sevincek R, Akgul O, Aygun M. Positionalisomeric effect on the crystallization of chlorine-substitutedN-phenyl-2-phthalimidoethanesulfonamide derivatives. ActaCrystallogr Sect C Struct Chem 2015; 71: 839–43.
31. Lien EJC, Hansch C, Anderson SM. Structure-activitycorrelations for antibacterial agents on gram-positive andgram-negative cells. J Med Chem 1968; 11: 430–41.
32. Ozkan-Ariksoysal D, Akgul O, Aydinlik S, Topkaya SN, AladagN, Ozsoz M. New electroactive hybridization indicators2-phthalimido-N-substitutedphenylethane-sulfonamidederivatives for biosensor applications: Ring substituent effecton interaction between compound and DNA. Electroanalysis2010; 22: 2225–34.
33. Gold HS. Vancomycin-Resistant Enterococci: Mechanisms andclinical observations. Clin Infect Dis 2001; 33: 210–9.34. Marothi YA, Agnihotri H, Dubey D. Enterococcal resistance-anoverview. Indian J Med Microbiol 2005; 23: 214–9.
35. http://www.molinspiration.com/cgi-bin/properties (LastAccess: 01.12.2016 )
36. Mujumdar P, Teruya K, Tonissen KF, Vullo D, Supuran CT,Peat TS, Poulsen S. An unusual natural product primarysulfonamide: Synthesis, carbonic anhydrase inhibition, andprotein X-ray structures of psammaplin C. J Med Chem 2016;59: 5462–70.
37. Li L, Li Z, Wang K, Liu Y, Li Y, Wang Q. Synthesis and antiviral,insecticidal, and fungicidal activities of gossypol derivativescontaining alkylimine, oxime or hydrazine moiety. BioorgMed Chem 2016; 24: 474–83.
38. Usifoh CO, Lambert DM, Wouters J, Scriba GKE. Synthesisand anticonvulsant activity of N,N-phthaloyl derivatives of (Weinheim) 2001; 334: 323–31.
39. Chatterjee S, Mallamo JP, Bihovsky R, Wells GJ, inventor;Cephalon INC. Peptide-containing α-ketoamide cysteineand serine protease inhibitors. WO 99/17790 A1 PCT/US1998/021055. 15 Apr. 1999.
40. Performance Standards for Antimicrobial SusceptibilityTesting; Twenty-Fifth Informational Supplement. CLSIdocument M100-S25. Wayne, PA: Clinical and LaboratoryStandards Institute; 2015.
41. Wayne, PA: Clinical and Laboratory Standards Institute; 2009.42. Kotmakci M, Ozturk İ, Kantarci G, Ermertcan Ş.Characterization and antimicrobial activity of novel hazelnutoil microemulsion loaded with Mitomycin C. Lat Am J Pharm2015; 34: 529–36.

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Yıl 2017, Cilt: 21 Sayı: 2, 361 - 370, 01.04.2017

Özlem Akgül İsmail Öztürk Abdurrahman Aygül Şafak Ermertcan

https://doi.org/10.12991/marupj.300894

Öz

Bu çalışmada, bir seri taurinamit türevi sentezlenmiş ve

antimikrobiyal aktiviteleri test edilmiştir. Yeni sentezlenen

11-15 no’lu bileşiklerin yapıları 1H NMR, IR, MS-APCI

ve elementel analiz yöntemleri ile aydınlatılmıştır. Hedef

bileşiklerin (1-15), antimikrobiyal aktiviteleri disk diffüzyon

ve mikrodilüsyon yöntemleri kullanılarak, Gram(+),

Gram(−) bakteri ve mantar standart suşlarına karşı

gerçekleştirilmiştir. Bileşiklerin çözünürlük özelliklerinden

dolayı disk diffüzyon testi ile karşılaştırılabilir sonuçlar

alınamasa da, mikrodilüsyon yöntemi sonuçları bileşiklerin

sadece Enterococcus faecalis üzerinde değişen oranlarda

etkili olduklarını göstermiştir. Elde edilen bilgilerle;

ftalimido, sekonder sülfonamit ve fenil halkasındaki

elektron verici grupların antibakteriyel aktivite için

gerekli olduğu sonucuna varılmıştır. Test edilen bileşikler

arasından, N-fenil-2-ftalimidotaurinamit’in fenil halkasının

para konumundan metil ve metoksi ile sübstitüe edildiği

türevlerin (4, 7), standart

Anahtar Kelimeler

Taurinamit, N-sübstitüe-2- ftalimidoetansülfonamit, antibakteriyel, Enterococcus faecalis, mikrodilüsyon

Kaynakça

1. Docquier JD, Cusi MG. Editorial overview: Anti-infectives:Towards novel antiviral and antibacterial drugs? Currentapproaches to address a growing medical need. Curr OpinPharmacol 2014; 18: iv–vi.
2. Davis DC, Mohammad H, Kyei-Baffour K, Younis W, CreemerCN, Seleem MN, Dai, M. Discovery and characterization ofaryl isonitriles as a new class of compounds versus methicillinandvancomycin-resistant Staphylococcus aureus. Eur J MedChem 2015; 101: 384–90.
3. Qin W, Panunzio M, Biondi S. β-Lactam AntibioticsRenaissance. Antibiotics 2014; 3: 193–215.
4. Walsh CT, Wencewicz TA. Prospects for new antibiotics: amolecule-centered perspective. J Antibiot 2014; 67: 7–22.
5. Elumalai K, Ali MA, Elumalai M, Eluri K, Srinivasan S,Sivannan S, Mohanthi SK. Synthesis, characterization andbiological evaluation of acetazolamide, cycloserine andisoniazid condensed some novel phthalimide derivatives. IntJ Chem Anal Sci 2013; 4: 57–61.
6. Orzeszko A, Kamińska B, Starościak BJ. Synthesis andantimicrobial activity of new adamantane derivatives III.Farmaco 2002; 57: 619–24.
7. Sachan D, Singh JP, Sachan D, Gangwar S. Design, synthesisand antimicrobial evaluation of mannich bases of novelisoindole analogues. Am J PharmTech Res 2012;2: 491-7.
8. Kamiński K, Obniska J, Wiklik B, Atamanyuk D. Synthesisand anticonvulsant properties of new acetamide derivativesof phthalimide, and its saturated cyclohexane and norborneneanalogs. Eur J Med Chem 2011; 46: 4634–41.
9. Santos JL, Yamasaki PR, Chin CM, Takashi CH, PavanFR, Leite CQF. Synthesis and in vitro anti Mycobacteriumtuberculosis activity of a series of phthalimide derivatives.Bioorg Med Chem 2009; 17: 3795–9.
10. Yang YJ, Yang YN, Jiang JS, Feng ZM, Liu HY, Pan XD, Zhang,PC. Synthesis and cytotoxic activity of heterocycle-substitutedphthalimide derivatives. Chin Chem Lett 2010; 21: 902–4.
11. Lima LM, Castro P, Machado AL, Fraga CAM, Lugnier C, DeMoraes VLG, Barreiro, EJ. Synthesis and anti-inflammatoryactivity of phthalimide derivatives, designed as newthalidomide analogues. Bioorg Med Chem 2002; 10: 3067–73.
12. Winterbottom R, Clapp JW, Miller WH, English JP, RoblinRO. Studies in chemotherapy. XV. Amides of pantoyltaurine 1.J Am Chem Soc 1947; 69: 1393–1401.
13. Smits RA, Adami M, Istyastono EP, Zuiderveld OP, van DamCME, de Kanter FJJ, Jongejan A, Coruzzi G, Leurs R, de EschIJP. Synthesis and QSAR of quinazoline sulfonamides ashighly potent human histamine H4 receptor inverse agonists.J Med Chem 2010; 53: 2390–2400.
14. Chung MC, Malatesta P, Bosquesi PL, Yamasaki PR, dosSantos JL, Vizioli EO. Advances in drug design based on theamino acid approach: Taurine analogues for the treatment ofCNS diseases. Pharmaceuticals 2012; 5: 1128–46.
15. Sharma R, Soman SS. Design and synthesis of sulfonamidederivatives of pyrrolidine and piperidine as anti-diabeticagents. Eur J Med Chem 2015; 90: 342–50.
16. Capasso C, Supuran CT. Anti-infective carbonic anhydraseinhibitors: A patent and literature review. Expert Opin TherPat 2013; 23: 693–704.
17. Supuran CT, Casini A, Scozzafava A. Protease inhibitors of thesulfonamide type: Anticancer, antiinflammatory, and antiviralagents. Med Res Rev 2003; 23: 535–58.
18. Kumar M, Ramasamy K, Mani V, Mishra RK, MajeedABA, Clercq ED, Narasimhan, B. Synthesis, antimicrobial,anticancer, antiviral evaluation and QSAR studies of 4-(1-aryl-2-oxo-1,2-dihydro-indol-3-ylideneamino)-N-substitutedbenzene sulfonamides. Arab J Chem 2014; 7: 396–408.
19. Chohan ZH, Youssoufi MH, Jarrahpour A, Ben Hadda T.Identification of antibacterial and antifungal pharmacophoresites for potent bacteria and fungi inhibition: Indolenylsulfonamide derivatives. Eur J Med Chem 2010; 45: 1189–99.
20. Zani F, Vicini P, Incerti M. Synthesis and antimicrobialproperties of 2-(benzylidene-amino)benzo[d]isothiazol-3-ones. Eur J Med Chem 2004; 39: 135–40.
21. Jarrahpour A, Shirvani P, Sharghi H, Aberi M, Sinou V,Latour C, Brunel J. Synthesis of novel mono- and bis-Schiffbases of morpholine derivatives and the investigation of theirantimalarial and antiproliferative activities. Med Chem Res2015; 24: 4105–12.
22. Oliveira MTA, Teixeira AMR, Cassiano CJM, Sena DM,Coutinho HDM, Menezes IRA, Figueredo FG, Silva LE, ToledoTA, Bento RR.F. Modulation of the antibiotic activity againstmultidrug resistant strains of 4-(phenylsulfonyl) morpholine.Saudi J Biol Sci 2016; 23: 34–8.
23. Akgul O, Sultan Kılıc F, Erol K, Pabuccuoglu V. Synthesisand anticonvulsant activity of some N-Phenyl-2-phtalimidoethanesulfonamide derivatives. Arch Pharm(Weinheim) 2007; 340: 656–60.
24. Romanowski EG, Yates KA, Teuchner B, Nagl M, Irschick EU,Gordon YJ. N-Chlorotaurine is an effective antiviral agentagainst adenovirus in vitro and in the Ad5/NZW rabbit ocularmodel. Invest Ophthalmol Vis Sci 2006; 47: 2021–6.
25. Corte DL, Crichton, RR, Duburs G, Nolan K, Tipton KF,Tirzitis G, Ward RJ. The use of taurine analogues to investigatetaurine functions and their potential therapeutic applications.Amino Acids 2002; 23: 367–79.
26. Curley OMS, McCormick JE, McElhinney RS, McMurryTBH. Intermediates in the Ing Manske reaction. Arkivoc 2003;7: 180–9.
27. Jorgensen JH, Ferraro MJ. Antimicrobial susceptibility testing:A review of general principles and contemporary practices.Clin Infect Dis 2009; 49: 1749–55.
28. Bielenica A, Stefanska J, Stepien K, Napiorkowska A,Augustynowicz-Kopec E, Sanna G, Madeddu, S, Boi S,Giliberti G, Wrzosek M, Struga M. Synthesis, cytotoxicity andantimicrobial activity of thiourea derivatives incorporating3-(trifluoromethyl)phenyl moiety. Eur J Med Chem 2015; 101:111–25.
29. De Almeida CG, Garbois GD, Amaral LM, Diniz CC, LeHyaric M. Relationship between structure and antibacterialactivity of lipophilic N-acyldiamines. Biomed Pharmacother2010; 64: 287–90.
30. Koktaş Koca S, Sevincek R, Akgul O, Aygun M. Positionalisomeric effect on the crystallization of chlorine-substitutedN-phenyl-2-phthalimidoethanesulfonamide derivatives. ActaCrystallogr Sect C Struct Chem 2015; 71: 839–43.
31. Lien EJC, Hansch C, Anderson SM. Structure-activitycorrelations for antibacterial agents on gram-positive andgram-negative cells. J Med Chem 1968; 11: 430–41.
32. Ozkan-Ariksoysal D, Akgul O, Aydinlik S, Topkaya SN, AladagN, Ozsoz M. New electroactive hybridization indicators2-phthalimido-N-substitutedphenylethane-sulfonamidederivatives for biosensor applications: Ring substituent effecton interaction between compound and DNA. Electroanalysis2010; 22: 2225–34.
33. Gold HS. Vancomycin-Resistant Enterococci: Mechanisms andclinical observations. Clin Infect Dis 2001; 33: 210–9.34. Marothi YA, Agnihotri H, Dubey D. Enterococcal resistance-anoverview. Indian J Med Microbiol 2005; 23: 214–9.
35. http://www.molinspiration.com/cgi-bin/properties (LastAccess: 01.12.2016 )
36. Mujumdar P, Teruya K, Tonissen KF, Vullo D, Supuran CT,Peat TS, Poulsen S. An unusual natural product primarysulfonamide: Synthesis, carbonic anhydrase inhibition, andprotein X-ray structures of psammaplin C. J Med Chem 2016;59: 5462–70.
37. Li L, Li Z, Wang K, Liu Y, Li Y, Wang Q. Synthesis and antiviral,insecticidal, and fungicidal activities of gossypol derivativescontaining alkylimine, oxime or hydrazine moiety. BioorgMed Chem 2016; 24: 474–83.
38. Usifoh CO, Lambert DM, Wouters J, Scriba GKE. Synthesisand anticonvulsant activity of N,N-phthaloyl derivatives of (Weinheim) 2001; 334: 323–31.
39. Chatterjee S, Mallamo JP, Bihovsky R, Wells GJ, inventor;Cephalon INC. Peptide-containing α-ketoamide cysteineand serine protease inhibitors. WO 99/17790 A1 PCT/US1998/021055. 15 Apr. 1999.
40. Performance Standards for Antimicrobial SusceptibilityTesting; Twenty-Fifth Informational Supplement. CLSIdocument M100-S25. Wayne, PA: Clinical and LaboratoryStandards Institute; 2015.
41. Wayne, PA: Clinical and Laboratory Standards Institute; 2009.42. Kotmakci M, Ozturk İ, Kantarci G, Ermertcan Ş.Characterization and antimicrobial activity of novel hazelnutoil microemulsion loaded with Mitomycin C. Lat Am J Pharm2015; 34: 529–36.

Toplam 40 adet kaynakça vardır.

Ayrıntılar

Konular	Sağlık Kurumları Yönetimi
Bölüm	Makaleler
Yazarlar	Özlem Akgül İsmail Öztürk Bu kişi benim Abdurrahman Aygül Bu kişi benim Şafak Ermertcan Bu kişi benim
Yayımlanma Tarihi	1 Nisan 2017
Yayımlandığı Sayı	Yıl 2017 Cilt: 21 Sayı: 2

Kaynak Göster

APA	Akgül, Ö., Öztürk, İ., Aygül, A., Ermertcan, Ş. (2017). Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives. Marmara Pharmaceutical Journal, 21(2), 361-370. https://doi.org/10.12991/marupj.300894
AMA	Akgül Ö, Öztürk İ, Aygül A, Ermertcan Ş. Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives. mpj. Mayıs 2017;21(2):361-370. doi:10.12991/marupj.300894
Chicago	Akgül, Özlem, İsmail Öztürk, Abdurrahman Aygül, ve Şafak Ermertcan. “Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives”. Marmara Pharmaceutical Journal 21, sy. 2 (Mayıs 2017): 361-70. https://doi.org/10.12991/marupj.300894.
EndNote	Akgül Ö, Öztürk İ, Aygül A, Ermertcan Ş (01 Mayıs 2017) Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives. Marmara Pharmaceutical Journal 21 2 361–370.
IEEE	Ö. Akgül, İ. Öztürk, A. Aygül, ve Ş. Ermertcan, “Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives”, mpj, c. 21, sy. 2, ss. 361–370, 2017, doi: 10.12991/marupj.300894.
ISNAD	Akgül, Özlem vd. “Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives”. Marmara Pharmaceutical Journal 21/2 (Mayıs 2017), 361-370. https://doi.org/10.12991/marupj.300894.
JAMA	Akgül Ö, Öztürk İ, Aygül A, Ermertcan Ş. Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives. mpj. 2017;21:361–370.
MLA	Akgül, Özlem vd. “Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives”. Marmara Pharmaceutical Journal, c. 21, sy. 2, 2017, ss. 361-70, doi:10.12991/marupj.300894.
Vancouver	Akgül Ö, Öztürk İ, Aygül A, Ermertcan Ş. Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives. mpj. 2017;21(2):361-70.

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