Research Article
BibTex RIS Cite

Yeni Tiofen Türevlerin Sentezlenmesi ve Karakterizasyonu

Year 2019, , 111 - 120, 01.03.2019
https://doi.org/10.21597/jist.422537

Abstract

Kararlı bir yapıya sahip tiyofen türevlerinin ziraat, gıda ve ilaç sanayilerinde kullanımı farklı türevlerinin sentezlenmesi gerekliliğini ortaya koymuştur. Bu amaçla, mevcut çalışmada bazı substitüe tiofen türevleri tasarlanıp sentezlendi. Sentezlenen bileşiklerin karakterizasyonu, spektroskopik yöntemlerle belirlendi. Bu bileşiklerin (3-9, 10a-e, 11-13) olası antimikrobiyal aktiviteleri gram pozitif (Bacillus subtilis ATCC 6633, Staphylococcus aureus 6538) ve gram negatif (Enterobacter aerogenes ATCC 13048, Escherichia coli) bakterilere karşı disk difüzyon metodu ile ölçüldü. Sentezlenen substitüe tiofen bileşiklerinin test bakterilerine karşı herhangi bir aktivite göstermediği belirlendi.

References

  • Andersson CD, Karlberg T, Ekblad T, Lindgren AE, Thorsell AG, Spjut S, Elofsson M, 2012. Discovery of ligands for ADP-ribosyltransferases via docking-based virtual screening. Journal Medicinal Chemistry 55:17 7706-7718.
  • Christophe M, Sylvain G, Christian L, Maria RP, Frederic F, Cyril I, Michel B, 2011. Synthesis and biological activities of triazole derivatives as inhibitors of InhA and antituberculosis agents. European Journal of Medicinal Chemistry 46:11 5524-5531.
  • Fakhr IMI, Radwan MAAS. El-Batran O, Abd El-Salam ME, El-Shenawy SM, 2009. Synthesis and pharmacological evaluation of 2-substituted benzo [b] thiophenes as anti-inflammatory and analgesic agents. European Journal of Medicinal Chemistry 44:4 1718-1725.
  • Gouda MA, Berghot MA, El-Ghani GEA, Khalil AM, 2010. Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety. European Journal of Medicinal Chemistry 45:4 1338-1345.
  • Isloor M, Kalluraya B, Pai KS, 2010. Synthesis, characterization and biological activities of some new benzo [b] thiophene derivatives. European Journal of Medicinal Chemistry 45:2 825-830.
  • Kuila BK, Nandi AK, 2006. Structural Hierarchy in Melt-Processed Poly (3-hexyl thiophene)− Montmorillonite Clay Nanocomposites: Novel Physical, Mechanical, Optical, and Conductivity Properties. The Journal of Physical Chemistry B 110:4 1621-1631.
  • Maddila S, Pagadala R, Jonnalagadda S, 2013. 1,2,4-triazoles: a review of synthetic approaches and the biological activity. Letters in Organic Chemistry 10:10 693-714.
  • Meltzer RJ, Lewis AD, McMillan FH, Genzer JD, Leonard F, King JA, 1953. Antitubercular substances. III. Nonpyridinoid heterocyclic hydrazides. Journal of the American Pharmacists Association 42: 594-600.
  • Moghaddam FM, Boinee HZ, 2004. An efficient and facile one-step synthesis of highly substituted thiophenes. Tetrahedron 60:29 6085-6089.
  • Mortaheb HR, Ghaemmaghami F, Mokhtarani B, 2012. A review on removal of sulfur components from gasoline by pervaporation. Chemical Engineering Research and Design 90:3 409-432.
  • Naresh P, Pattanaik P, Priyadarshini RL, Reddy DR, 2013. Synthetic characterization antimicrobial screening of some novel 6-fluorobenzothiazole substituted [1,2,4] triazole analogues. International Journal of Pharmacy and Pharmaceutical Sciences 1: 18-24.
  • Parai MK, Panda G, Chaturvedi V, Manju YK, Sinha S. 2008. Thiophene containing triarylmethanes as antitubercular agents. Bioorganic Medicinal Chemistry Letters 18 (1): 289-292.
  • Patel R, Kumari P, Chikhalia K, 2013. New quinolinyl-1, 3,4-oxadiazoles: Synthesis, in vitro antibacterial, antifungal and antituberculosis studies. Medicinal Chemistry 9:4 596-607.
  • Pinto E, Queiroz MRP. Vale-Silva LA, Oliveira JF, Begouin A, Begouin JM, Kirsch G, 2008. Antifungal activity of synthetic di (hetero) arylamines based on the benzo [b] thiophene moiety. Bioorganic Medicinal Chemistry 16:17 8172-8177.
  • Ramazani A, Rezaei A, 2010. Novel one-pot, four-component condensation reaction: An efficient approach for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives by a Ugi-4CR/aza-wittig sequence. Organic Letter 12:12 2852-2855.
  • Roncali J, 1992. Conjugated poly (thiophenes): synthesis, functionalization, and applications. Chemical Reviews 92:4 711-738.
  • Ren S, Wang R, Komatsu K, Bonaz-Krause P, Zyrianov Y, McKenna CE, Csipke C, Tokes ZA, Lien EJ, 2002. Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. Journal of Medicinal Chemistry 45:2 410-419.
  • Sagardoy AA, Gil MJ, Villar R, Viñas M, Arrazola A, Encío I, Martinez-Merino V, 2010. Benzo [b] thiophene-6-carboxamide 1, 1-dioxides: Inhibitors of human cancer cell growth at nanomolar concentrations. Bioorganic Medicinal Chemistry 18:15 5701-5706.
  • Zarudnitskii EV, Pervak II, Merkulov AS, Yurchenko AA, Tolmachev AA, 2008.Trimethylsilyl-1, 3, 4-oxadiazoles-new useful synthons for the synthesis of various 2, 5-disubstituted-1, 3, 4-oxadiazoles. Tetrahedron 64:45 10431-10442.
  • William OF, Principles of Medicinal Chemistry, 3rd ed. Lippincott Williams Wilkins Publication, Philadelphia, USA, p. 651 1989.
  • Zhang L, Zhang A, Chen X, Lei X, Nan X, Chen D, Zhang Z, 2002. Synthesis and Biological Activity of 3-(2-Furanyl)-6-Aryl-1, 2, 4-Triazolo [3,4-b]-1,3,4-Thiadiazoles. Molecules 7: 681-689.

Synthesis and Characterization of the Novel Thiophene Derivatives

Year 2019, , 111 - 120, 01.03.2019
https://doi.org/10.21597/jist.422537

Abstract

The use of thiophene derivatives that have a stable structure in agriculture, food and pharmaceutical industries has revealed the necessity of synthesizing different derivatives. For this purpose, in the current study, some substituted thiophene derivatives have been designed and synthesized. The characterization of the synthesized compounds was determined by spectroscopic methods. The possible antimicrobial activities of these compounds (3-9, 10a-e, 11-13) were measured by disc diffusion method against gram positive (Bacillus subtilis ATCC 6633, Staphylococcus aureus 6538) and gram negative (Enterobacter aerogenes ATCC 13048, Escherichia coli) bacteria. The synthesized substituted thiophene compounds do not showed any antibacterial activities against test bacteria.

References

  • Andersson CD, Karlberg T, Ekblad T, Lindgren AE, Thorsell AG, Spjut S, Elofsson M, 2012. Discovery of ligands for ADP-ribosyltransferases via docking-based virtual screening. Journal Medicinal Chemistry 55:17 7706-7718.
  • Christophe M, Sylvain G, Christian L, Maria RP, Frederic F, Cyril I, Michel B, 2011. Synthesis and biological activities of triazole derivatives as inhibitors of InhA and antituberculosis agents. European Journal of Medicinal Chemistry 46:11 5524-5531.
  • Fakhr IMI, Radwan MAAS. El-Batran O, Abd El-Salam ME, El-Shenawy SM, 2009. Synthesis and pharmacological evaluation of 2-substituted benzo [b] thiophenes as anti-inflammatory and analgesic agents. European Journal of Medicinal Chemistry 44:4 1718-1725.
  • Gouda MA, Berghot MA, El-Ghani GEA, Khalil AM, 2010. Synthesis and antimicrobial activities of some new thiazole and pyrazole derivatives based on 4,5,6,7-tetrahydrobenzothiophene moiety. European Journal of Medicinal Chemistry 45:4 1338-1345.
  • Isloor M, Kalluraya B, Pai KS, 2010. Synthesis, characterization and biological activities of some new benzo [b] thiophene derivatives. European Journal of Medicinal Chemistry 45:2 825-830.
  • Kuila BK, Nandi AK, 2006. Structural Hierarchy in Melt-Processed Poly (3-hexyl thiophene)− Montmorillonite Clay Nanocomposites: Novel Physical, Mechanical, Optical, and Conductivity Properties. The Journal of Physical Chemistry B 110:4 1621-1631.
  • Maddila S, Pagadala R, Jonnalagadda S, 2013. 1,2,4-triazoles: a review of synthetic approaches and the biological activity. Letters in Organic Chemistry 10:10 693-714.
  • Meltzer RJ, Lewis AD, McMillan FH, Genzer JD, Leonard F, King JA, 1953. Antitubercular substances. III. Nonpyridinoid heterocyclic hydrazides. Journal of the American Pharmacists Association 42: 594-600.
  • Moghaddam FM, Boinee HZ, 2004. An efficient and facile one-step synthesis of highly substituted thiophenes. Tetrahedron 60:29 6085-6089.
  • Mortaheb HR, Ghaemmaghami F, Mokhtarani B, 2012. A review on removal of sulfur components from gasoline by pervaporation. Chemical Engineering Research and Design 90:3 409-432.
  • Naresh P, Pattanaik P, Priyadarshini RL, Reddy DR, 2013. Synthetic characterization antimicrobial screening of some novel 6-fluorobenzothiazole substituted [1,2,4] triazole analogues. International Journal of Pharmacy and Pharmaceutical Sciences 1: 18-24.
  • Parai MK, Panda G, Chaturvedi V, Manju YK, Sinha S. 2008. Thiophene containing triarylmethanes as antitubercular agents. Bioorganic Medicinal Chemistry Letters 18 (1): 289-292.
  • Patel R, Kumari P, Chikhalia K, 2013. New quinolinyl-1, 3,4-oxadiazoles: Synthesis, in vitro antibacterial, antifungal and antituberculosis studies. Medicinal Chemistry 9:4 596-607.
  • Pinto E, Queiroz MRP. Vale-Silva LA, Oliveira JF, Begouin A, Begouin JM, Kirsch G, 2008. Antifungal activity of synthetic di (hetero) arylamines based on the benzo [b] thiophene moiety. Bioorganic Medicinal Chemistry 16:17 8172-8177.
  • Ramazani A, Rezaei A, 2010. Novel one-pot, four-component condensation reaction: An efficient approach for the synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazole derivatives by a Ugi-4CR/aza-wittig sequence. Organic Letter 12:12 2852-2855.
  • Roncali J, 1992. Conjugated poly (thiophenes): synthesis, functionalization, and applications. Chemical Reviews 92:4 711-738.
  • Ren S, Wang R, Komatsu K, Bonaz-Krause P, Zyrianov Y, McKenna CE, Csipke C, Tokes ZA, Lien EJ, 2002. Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. Journal of Medicinal Chemistry 45:2 410-419.
  • Sagardoy AA, Gil MJ, Villar R, Viñas M, Arrazola A, Encío I, Martinez-Merino V, 2010. Benzo [b] thiophene-6-carboxamide 1, 1-dioxides: Inhibitors of human cancer cell growth at nanomolar concentrations. Bioorganic Medicinal Chemistry 18:15 5701-5706.
  • Zarudnitskii EV, Pervak II, Merkulov AS, Yurchenko AA, Tolmachev AA, 2008.Trimethylsilyl-1, 3, 4-oxadiazoles-new useful synthons for the synthesis of various 2, 5-disubstituted-1, 3, 4-oxadiazoles. Tetrahedron 64:45 10431-10442.
  • William OF, Principles of Medicinal Chemistry, 3rd ed. Lippincott Williams Wilkins Publication, Philadelphia, USA, p. 651 1989.
  • Zhang L, Zhang A, Chen X, Lei X, Nan X, Chen D, Zhang Z, 2002. Synthesis and Biological Activity of 3-(2-Furanyl)-6-Aryl-1, 2, 4-Triazolo [3,4-b]-1,3,4-Thiadiazoles. Molecules 7: 681-689.
There are 21 citations in total.

Details

Primary Language English
Subjects Engineering, Chemical Engineering
Journal Section Kimya / Chemistry
Authors

Adnan Çetin 0000-0001-6487-9489

Havva Kurt This is me 0000-0002-2951-1934

Sedat Bozarı This is me 0000-0001-5265-2236

Publication Date March 1, 2019
Submission Date May 10, 2018
Acceptance Date September 24, 2018
Published in Issue Year 2019

Cite

APA Çetin, A., Kurt, H., & Bozarı, S. (2019). Synthesis and Characterization of the Novel Thiophene Derivatives. Journal of the Institute of Science and Technology, 9(1), 111-120. https://doi.org/10.21597/jist.422537
AMA Çetin A, Kurt H, Bozarı S. Synthesis and Characterization of the Novel Thiophene Derivatives. J. Inst. Sci. and Tech. March 2019;9(1):111-120. doi:10.21597/jist.422537
Chicago Çetin, Adnan, Havva Kurt, and Sedat Bozarı. “Synthesis and Characterization of the Novel Thiophene Derivatives”. Journal of the Institute of Science and Technology 9, no. 1 (March 2019): 111-20. https://doi.org/10.21597/jist.422537.
EndNote Çetin A, Kurt H, Bozarı S (March 1, 2019) Synthesis and Characterization of the Novel Thiophene Derivatives. Journal of the Institute of Science and Technology 9 1 111–120.
IEEE A. Çetin, H. Kurt, and S. Bozarı, “Synthesis and Characterization of the Novel Thiophene Derivatives”, J. Inst. Sci. and Tech., vol. 9, no. 1, pp. 111–120, 2019, doi: 10.21597/jist.422537.
ISNAD Çetin, Adnan et al. “Synthesis and Characterization of the Novel Thiophene Derivatives”. Journal of the Institute of Science and Technology 9/1 (March 2019), 111-120. https://doi.org/10.21597/jist.422537.
JAMA Çetin A, Kurt H, Bozarı S. Synthesis and Characterization of the Novel Thiophene Derivatives. J. Inst. Sci. and Tech. 2019;9:111–120.
MLA Çetin, Adnan et al. “Synthesis and Characterization of the Novel Thiophene Derivatives”. Journal of the Institute of Science and Technology, vol. 9, no. 1, 2019, pp. 111-20, doi:10.21597/jist.422537.
Vancouver Çetin A, Kurt H, Bozarı S. Synthesis and Characterization of the Novel Thiophene Derivatives. J. Inst. Sci. and Tech. 2019;9(1):111-20.