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Yeni Tiofen Türevlerin Sentezlenmesi ve Karakterizasyonu

Yıl 2019, Cilt: 9 Sayı: 1, 111 - 120, 01.03.2019

Adnan Çetin , Havva Kurt Sedat Bozarı

https://doi.org/10.21597/jist.422537
Cited By: 1

Öz

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.

Anahtar Kelimeler

Heterosiklik bileşikler hidrazid tiofen okzadiazol pirazol

Kaynakça

  • 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

Yıl 2019, Cilt: 9 Sayı: 1, 111 - 120, 01.03.2019

Adnan Çetin , Havva Kurt Sedat Bozarı

https://doi.org/10.21597/jist.422537
Cited By: 1

Öz

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.

Anahtar Kelimeler

Heterocyclic compounds hydrazide thiophene oxadiazole pyrazole

Kaynakça

  • 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.
Toplam 21 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik, Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

Adnan Çetin 0000-0001-6487-9489

Havva Kurt Bu kişi benim 0000-0002-2951-1934

Sedat Bozarı Bu kişi benim 0000-0001-5265-2236

Yayımlanma Tarihi 1 Mart 2019
Gönderilme Tarihi 10 Mayıs 2018
Kabul Tarihi 24 Eylül 2018
Yayımlandığı Sayı Yıl 2019 Cilt: 9 Sayı: 1

Kaynak Göster

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. Iğdır Üniv. Fen Bil Enst. Der. Mart 2019;9(1):111-120. doi:10.21597/jist.422537
Chicago Çetin, Adnan, Havva Kurt, ve Sedat Bozarı. “Synthesis and Characterization of the Novel Thiophene Derivatives”. Journal of the Institute of Science and Technology 9, sy. 1 (Mart 2019): 111-20. https://doi.org/10.21597/jist.422537.
EndNote Çetin A, Kurt H, Bozarı S (01 Mart 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, ve S. Bozarı, “Synthesis and Characterization of the Novel Thiophene Derivatives”, Iğdır Üniv. Fen Bil Enst. Der., c. 9, sy. 1, ss. 111–120, 2019, doi: 10.21597/jist.422537.
ISNAD Çetin, Adnan vd. “Synthesis and Characterization of the Novel Thiophene Derivatives”. Journal of the Institute of Science and Technology 9/1 (Mart 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. Iğdır Üniv. Fen Bil Enst. Der. 2019;9:111–120.
MLA Çetin, Adnan vd. “Synthesis and Characterization of the Novel Thiophene Derivatives”. Journal of the Institute of Science and Technology, c. 9, sy. 1, 2019, ss. 111-20, doi:10.21597/jist.422537.
Vancouver Çetin A, Kurt H, Bozarı S. Synthesis and Characterization of the Novel Thiophene Derivatives. Iğdır Üniv. Fen Bil Enst. Der. 2019;9(1):111-20.

Cited By

Synthesis of Tetrasubstituted Thiophenes Starting from Amino Mercaptoacrylates and α-brominated Acetamides
Current Organic Chemistry
https://doi.org/10.2174/1385272825666210111112449