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Synthesis and Antioxidant Activities of New 2-(4-methylphenylsulphonyl)-5-Aryl-1,3,4-Oxadiazole Compounds

Year 2021, Volume: 14 Issue: 1, 232 - 240, 31.03.2021
https://doi.org/10.18185/erzifbed.823431

Abstract

Bu çalışmada, antioksidan aktiviteye sahip bazı yeni heterosiklik oksadiazol türevlerinin sentezlenmesi amaçlanmıştır. 1,3,4-oksadiazoller, 4-metilfenilsülfonilhidrazidin farklı aromatik asitlerle POCl3 varlığında kondenzasyon reaksiyonu sonucu elde edilmiştir. Sentezlenen bileşiklerin yapıları 1H NMR ve 13C NMR spektroskopisi kullanılarak desteklenmiş ayrıca ince tabaka kromotografisi kullanılarak saflıkları kontrol edilmiştir. Elementel analizleri Carlo Erba 1106 elementel analiz cihazında yapılmıştır. 2,5-disübstitüye-1,3,4-oksadiazol türevlerinin (1-5) antioksidan aktiviteleri, ABTS (2,2′-Azino-bis(3-etilbenzenotiyazolin-6-sülfonik asid), DPPH (1,1-difenil-2-pikrilhidrazil) radikal giderme aktiviteleri ve demir indirgeme gücü antioksidan kapasitesine göre incelenmiştir. Elde edilen sonuçlar, sentezlenen bileşiklerin (1-5) etkili antioksidan aktiviteye sahip olduğunu göstermiştir.

References

  • Abadi, A.H., Eissa, A.A. and Hassan, G.S. 2003. “Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents”, Chemical and Pharmaceutical Bulletin, 51, 838-844.
  • Aboraia, A.S., Abdel-Rahman, H.M., Mahfouz, N.M. and EL-Gendy, M.A. 2006. “Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: promising anticancer agents”, Bioorganic Medicinal Chemistry, 14, 1236-1246.
  • Akhilesh, K., Saritha, S.D., Souza, S., Nagaraj, S., Gaonkar, S. L., Bharathi, S. P., and Rai, K.M. 2009. “Antiangiogenic and antiproliferative effects of Substituted-1,3,4-oxadiazole derivatives is mediated by down regulation of VEGF and inhibition of translocation of HIF-1 alpha in Ehrlich ascites tumor cells”, Cancer Chemotherapy And Pharmacology, 64, 1221-1233.
  • Ali, A., Tatabai, S. A., Faizi, M., Kebriaeezadeh, A., Mehrabi, N., Dalvandi, A. and Shafiee, A. 2004. “Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles”, Bioorganic Medicinal Chemistry Letter, 14, 6057-6059.
  • Amir, M., Shikha, K. 2004. “Synthesis and anti-inflammatory, analgesis, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino)phenyl] acetic acid derivatives”, Eurepean Journal Medicinal Chemistry 39, 535-545.
  • Arnao, M. B., Cano, A. and Acosta, M. 2001. “The hydrophilic and lipophilic contribution to total antioxidant activity”, Food Chemistry, 73, 239-244.
  • Bankar, R.G., Nandakumar, K., Nayak, G. P., Thakur, A., Rao, C. M. and Kutty, N. G. 2009. “vasorelaxant effect in rat aortic rings through calcium channel blockage:a preliminary in vitro assessment of a 1,3,4-oxadiazole derivative”, Chemico-Biological Interactions, 181, 377-382.
  • Bhat, K.S., Karthikeyan, M. S., Holla, B.S. and Shetty, N.S. 2004. “Synthesis of some new fluorine containing 1,3,4-oxadiazole derivatives as potential antibacterial and anticancer agents”, Indian Journal of Chemistry-Section B, 43, 1765-1769.
  • Brand-Williams, W., Cuvelier, M.E. and Berset, C. 1995. “Use of a free radical method to evaluate antioxidant activity”, LWT-Food Science and Technology, 28, 25-30.
  • Cao, S., Qian, X., Song, G. and Huang, Q. 2002. “Syntheses and insecticidal activity of new 2-(5-(trifluoromethyl)pyridyloxymethyl) -1,3,4-oxadiazoles”, Journal of Fluorine Chemistry, 117, 63-66.
  • El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. and Lehmann, J. 2004. “Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones”, Bioorganic & Medicinal Chemistry, 12, 5107-5113.
  • Filho, S., Jose, M., Lima, D., Jose, G. and Leite Lucia, F. C. 2009. “Synthesis, characterization, and anti-inflammatory evaluation of 1,2,4‐oxadiazoles combined with thiosemicarbazide and 1,3,4-oxadiazole moieties”, Indian Journal of Heterocyclic Chemistry, 46, 722-727.
  • Ghania, U., Ullah, N. 2010. “New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site”, Bioorganic & Medicinal Chemistry, 18, 4042-4048. Gumrukcuoglu, N. and Sokmen, B. 2019. “Some 2,5-disubstitue-1,3,4-oxadiazoles as new antioxidants”, The Black Sea Journal of Sciences, 9, 10-15.
  • Ilango, K., Valentina, P., Umarani, N., Kumar, T. and Young Pharm, J. 2009. “Synthesis and characterization of 2,5-disubstituted-1,3,4-oxadiazoles as potential anti-inflammatory agents”, Pharmaceutical Chemistry, 1, 72-76.
  • Jayashankar, B., Lokanath Rai, K.M., Baskaran, N. and Sathish, S.H. 2009. “Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as anti-ınflammatory and analgesic agents”, European Journal of Medicinal Chemistry, 44, 3898-3902.
  • Jha, K. K., Samad, A., Kumar, Y., Shaharyar, M., Khosa, R., Jain, J. and Bansal, S. 2009. “3D QSAR Studies of 1,3,4-oxadiazole derivatives as antimycobacterial agents”, Iranian Journal of Pharmaceutical Research, 8, 163-167.
  • Kachroo, P.L., Gupta, K., Gupta, S.C. and Gupta, A.K. 1990. “Synthesis of some substituted-1,3,4-oxadiazoles, their antibacterial, antiamebic activity”, National Academy Science Letters, 13, 125-126.
  • Khan, M.T., Choudhary, M.I., Khan, K.M. and Rani, M. 2005. “Structure–activity relationships of tyrosinase ınhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues”, Bioorganic & Medicinal Chemistry, 13, 3385-3395.
  • Kim, R. M., Rouse, E. A., Chapman, K. T. and Tata, J. R. 2004. “P1' Oxadiazole protease ınhibitors with excellent activity against native and protease ınhibitor-resistant HIV-1”, Bioorganic & Medicinal Chemistry Letters, 14, 4651-4654.
  • Maa, L., Xiao, L., Li, C., Xie, Z.L., Li, D.D., Wang, Y.T., Ma, H.T., Zhu, H.L., Wang, M.H. and Ye, Y.H. 2013. “Synthesis and antioxidant activity of novel mannich base of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan”, Bioorganic & Medicinal Chemistry, 21, 6763-6770.
  • Maslat, A.O., Abussaud, M., Tashtoush, H. and Mahmoud A.T. 2002. “Synthesis, antibacterial, antifungal and genotoxic activity of bis-1,3,4-oxadiazole derivatives”, Polish Journal of Pharmacology, 54, 55-59.
  • Mohan, T. P., Vishalakshi, B., Bhat, K. S., Rao, K. S. and Kendappa, G. N. 2004. “Synthesis and ınsecticidal activity of some 1,3,4-oxadiazole derivatives containing phenoxyfluorophenyl group”, Indian Journal of Chemistry -Section B, 43,1798-1801.
  • Oyaizu, M. 1986. “Studies on products of browning reactions: antioxidative activities of products of browning reaction prepared from glucosamine”, The Japanese Journal of Nutrition and Dietetics, 44, 307-315.
  • Palaska, E., Şahin, G., Kelicen, P., Durlu, N. T. ve Altınok, G. 2002. “Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones”, II Farmaco, 57, 101-107.
  • Pandeya, S. N., Sriram, D., Nath, G., and De Clercq, E. 2000. “Synthesis, antibacterial, antifungal and Anti-HIV evaluation of Schiff and mannich bases of ısatin and its derivatives with triazole”, Arzneim Forsch./Drug Research, 50, 55-59.
  • Rostom, S.A., Shalaby, M.A. and El-Demellawy, M.A. 2003. “Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1h-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents”, European Journal of Medicinal Chemistry, 38, 959-974.
  • Shaoyong, K., Zhong, L. and Xuhong, Q. 2008. “1,3,4-Oxadiazole-3(2H)-carboxamide derivatives as potential novel class of monoamine oxidase (mao) ınhibitors: synthesis, evaluation, and role of urea moiety”, Bioorganic & Medicinal Chemistry, 16, 7565-7572.
  • Zarghi, A., Hajimahdi, Z., Mohebbi, S., Rashidi, H., Mozaffari, S., Sarraf, S., Faizi, M., Tabatabaee, S. A. and Shafiee, A. 2008. “Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)-phenyl]-1,3,4-oxadiazoles as anticonvulsant agents”, Chemical and Pharmaceutical Bulletin, 56, 509-512.
  • Zarghi, A., Tatabai, S. A., Faizi, M., Ahadian, A., Navabi, P., Zanganeh, V. and Shafiee A. 2005. “Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles”, Bioorganic & Medicinal Chemistry Letters, 15, 1863-1865.
  • Zheng, X.J., Li, C.S., Cui, M.Y., Songa, Z.W., Bai, X.Q. Lianga, C.W., Wanga, H.Y. and Zhang, T.Y. 2020. “Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents”, Bioorganic & Medicinal Chemistry Letters, 30, 127237.
  • Zuhair, Z. M., Ghada, J., Elham, A. and Lina, N. 2008. “Antimicrobial activity of some new oxadiazole derivatives”, Jordan Journal of Chemistry, 3, 233-243.

Yeni 2-(4-metilfenilsülfonil)-5-Aril-1,3,4-Oksadiazol Bileşiklerinin Sentezi ve Antioksidan Aktiviteleri

Year 2021, Volume: 14 Issue: 1, 232 - 240, 31.03.2021
https://doi.org/10.18185/erzifbed.823431

Abstract

Bu çalışmada, antioksidan aktiviteye sahip bazı yeni heterosiklik oksadiazol türevlerinin sentezlenmesi amaçlanmıştır. 1,3,4-oksadiazoller, 4-metilfenilsülfonilhidrazidin farklı aromatik asitlerle POCl3 varlığında kondenzasyon reaksiyonu sonucu elde edilmiştir. Sentezlenen bileşiklerin yapıları 1H NMR ve 13C NMR spektroskopisi kullanılarak desteklenmiş ayrıca ince tabaka kromotografisi kullanılarak saflıkları kontrol edilmiştir. Elementel analizleri Carlo Erba 1106 elementel analiz cihazında yapılmıştır. 2,5-disübstitüye-1,3,4-oksadiazol türevlerinin (1-5) antioksidan aktiviteleri, ABTS (2,2′-Azino-bis(3-etilbenzenotiyazolin-6-sülfonik asid), DPPH (1,1-difenil-2-pikrilhidrazil) radikal giderme aktiviteleri ve demir indirgeme gücü antioksidan kapasitesine göre incelenmiştir. Elde edilen sonuçlar, sentezlenen bileşiklerin (1-5) etkili antioksidan aktiviteye sahip olduğunu göstermiştir.

References

  • Abadi, A.H., Eissa, A.A. and Hassan, G.S. 2003. “Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents”, Chemical and Pharmaceutical Bulletin, 51, 838-844.
  • Aboraia, A.S., Abdel-Rahman, H.M., Mahfouz, N.M. and EL-Gendy, M.A. 2006. “Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: promising anticancer agents”, Bioorganic Medicinal Chemistry, 14, 1236-1246.
  • Akhilesh, K., Saritha, S.D., Souza, S., Nagaraj, S., Gaonkar, S. L., Bharathi, S. P., and Rai, K.M. 2009. “Antiangiogenic and antiproliferative effects of Substituted-1,3,4-oxadiazole derivatives is mediated by down regulation of VEGF and inhibition of translocation of HIF-1 alpha in Ehrlich ascites tumor cells”, Cancer Chemotherapy And Pharmacology, 64, 1221-1233.
  • Ali, A., Tatabai, S. A., Faizi, M., Kebriaeezadeh, A., Mehrabi, N., Dalvandi, A. and Shafiee, A. 2004. “Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles”, Bioorganic Medicinal Chemistry Letter, 14, 6057-6059.
  • Amir, M., Shikha, K. 2004. “Synthesis and anti-inflammatory, analgesis, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino)phenyl] acetic acid derivatives”, Eurepean Journal Medicinal Chemistry 39, 535-545.
  • Arnao, M. B., Cano, A. and Acosta, M. 2001. “The hydrophilic and lipophilic contribution to total antioxidant activity”, Food Chemistry, 73, 239-244.
  • Bankar, R.G., Nandakumar, K., Nayak, G. P., Thakur, A., Rao, C. M. and Kutty, N. G. 2009. “vasorelaxant effect in rat aortic rings through calcium channel blockage:a preliminary in vitro assessment of a 1,3,4-oxadiazole derivative”, Chemico-Biological Interactions, 181, 377-382.
  • Bhat, K.S., Karthikeyan, M. S., Holla, B.S. and Shetty, N.S. 2004. “Synthesis of some new fluorine containing 1,3,4-oxadiazole derivatives as potential antibacterial and anticancer agents”, Indian Journal of Chemistry-Section B, 43, 1765-1769.
  • Brand-Williams, W., Cuvelier, M.E. and Berset, C. 1995. “Use of a free radical method to evaluate antioxidant activity”, LWT-Food Science and Technology, 28, 25-30.
  • Cao, S., Qian, X., Song, G. and Huang, Q. 2002. “Syntheses and insecticidal activity of new 2-(5-(trifluoromethyl)pyridyloxymethyl) -1,3,4-oxadiazoles”, Journal of Fluorine Chemistry, 117, 63-66.
  • El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. and Lehmann, J. 2004. “Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones”, Bioorganic & Medicinal Chemistry, 12, 5107-5113.
  • Filho, S., Jose, M., Lima, D., Jose, G. and Leite Lucia, F. C. 2009. “Synthesis, characterization, and anti-inflammatory evaluation of 1,2,4‐oxadiazoles combined with thiosemicarbazide and 1,3,4-oxadiazole moieties”, Indian Journal of Heterocyclic Chemistry, 46, 722-727.
  • Ghania, U., Ullah, N. 2010. “New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site”, Bioorganic & Medicinal Chemistry, 18, 4042-4048. Gumrukcuoglu, N. and Sokmen, B. 2019. “Some 2,5-disubstitue-1,3,4-oxadiazoles as new antioxidants”, The Black Sea Journal of Sciences, 9, 10-15.
  • Ilango, K., Valentina, P., Umarani, N., Kumar, T. and Young Pharm, J. 2009. “Synthesis and characterization of 2,5-disubstituted-1,3,4-oxadiazoles as potential anti-inflammatory agents”, Pharmaceutical Chemistry, 1, 72-76.
  • Jayashankar, B., Lokanath Rai, K.M., Baskaran, N. and Sathish, S.H. 2009. “Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as anti-ınflammatory and analgesic agents”, European Journal of Medicinal Chemistry, 44, 3898-3902.
  • Jha, K. K., Samad, A., Kumar, Y., Shaharyar, M., Khosa, R., Jain, J. and Bansal, S. 2009. “3D QSAR Studies of 1,3,4-oxadiazole derivatives as antimycobacterial agents”, Iranian Journal of Pharmaceutical Research, 8, 163-167.
  • Kachroo, P.L., Gupta, K., Gupta, S.C. and Gupta, A.K. 1990. “Synthesis of some substituted-1,3,4-oxadiazoles, their antibacterial, antiamebic activity”, National Academy Science Letters, 13, 125-126.
  • Khan, M.T., Choudhary, M.I., Khan, K.M. and Rani, M. 2005. “Structure–activity relationships of tyrosinase ınhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues”, Bioorganic & Medicinal Chemistry, 13, 3385-3395.
  • Kim, R. M., Rouse, E. A., Chapman, K. T. and Tata, J. R. 2004. “P1' Oxadiazole protease ınhibitors with excellent activity against native and protease ınhibitor-resistant HIV-1”, Bioorganic & Medicinal Chemistry Letters, 14, 4651-4654.
  • Maa, L., Xiao, L., Li, C., Xie, Z.L., Li, D.D., Wang, Y.T., Ma, H.T., Zhu, H.L., Wang, M.H. and Ye, Y.H. 2013. “Synthesis and antioxidant activity of novel mannich base of 1,3,4-oxadiazole derivatives possessing 1,4-benzodioxan”, Bioorganic & Medicinal Chemistry, 21, 6763-6770.
  • Maslat, A.O., Abussaud, M., Tashtoush, H. and Mahmoud A.T. 2002. “Synthesis, antibacterial, antifungal and genotoxic activity of bis-1,3,4-oxadiazole derivatives”, Polish Journal of Pharmacology, 54, 55-59.
  • Mohan, T. P., Vishalakshi, B., Bhat, K. S., Rao, K. S. and Kendappa, G. N. 2004. “Synthesis and ınsecticidal activity of some 1,3,4-oxadiazole derivatives containing phenoxyfluorophenyl group”, Indian Journal of Chemistry -Section B, 43,1798-1801.
  • Oyaizu, M. 1986. “Studies on products of browning reactions: antioxidative activities of products of browning reaction prepared from glucosamine”, The Japanese Journal of Nutrition and Dietetics, 44, 307-315.
  • Palaska, E., Şahin, G., Kelicen, P., Durlu, N. T. ve Altınok, G. 2002. “Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones”, II Farmaco, 57, 101-107.
  • Pandeya, S. N., Sriram, D., Nath, G., and De Clercq, E. 2000. “Synthesis, antibacterial, antifungal and Anti-HIV evaluation of Schiff and mannich bases of ısatin and its derivatives with triazole”, Arzneim Forsch./Drug Research, 50, 55-59.
  • Rostom, S.A., Shalaby, M.A. and El-Demellawy, M.A. 2003. “Polysubstituted pyrazoles, part 5. Synthesis of new 1-(4-chlorophenyl)-4-hydroxy-1h-pyrazole-3-carboxylic acid hydrazide analogs and some derived ring systems. A novel class of potential antitumor and anti-HCV agents”, European Journal of Medicinal Chemistry, 38, 959-974.
  • Shaoyong, K., Zhong, L. and Xuhong, Q. 2008. “1,3,4-Oxadiazole-3(2H)-carboxamide derivatives as potential novel class of monoamine oxidase (mao) ınhibitors: synthesis, evaluation, and role of urea moiety”, Bioorganic & Medicinal Chemistry, 16, 7565-7572.
  • Zarghi, A., Hajimahdi, Z., Mohebbi, S., Rashidi, H., Mozaffari, S., Sarraf, S., Faizi, M., Tabatabaee, S. A. and Shafiee, A. 2008. “Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)-phenyl]-1,3,4-oxadiazoles as anticonvulsant agents”, Chemical and Pharmaceutical Bulletin, 56, 509-512.
  • Zarghi, A., Tatabai, S. A., Faizi, M., Ahadian, A., Navabi, P., Zanganeh, V. and Shafiee A. 2005. “Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles”, Bioorganic & Medicinal Chemistry Letters, 15, 1863-1865.
  • Zheng, X.J., Li, C.S., Cui, M.Y., Songa, Z.W., Bai, X.Q. Lianga, C.W., Wanga, H.Y. and Zhang, T.Y. 2020. “Synthesis, biological evaluation of benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents”, Bioorganic & Medicinal Chemistry Letters, 30, 127237.
  • Zuhair, Z. M., Ghada, J., Elham, A. and Lina, N. 2008. “Antimicrobial activity of some new oxadiazole derivatives”, Jordan Journal of Chemistry, 3, 233-243.
There are 31 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Makaleler
Authors

Nurhan Gümrükçüoğlu 0000-0002-9669-6318

Bahar Bilgin Sökmen 0000-0003-3904-8178

Publication Date March 31, 2021
Published in Issue Year 2021 Volume: 14 Issue: 1

Cite

APA Gümrükçüoğlu, N., & Bilgin Sökmen, B. (2021). Synthesis and Antioxidant Activities of New 2-(4-methylphenylsulphonyl)-5-Aryl-1,3,4-Oxadiazole Compounds. Erzincan University Journal of Science and Technology, 14(1), 232-240. https://doi.org/10.18185/erzifbed.823431