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(1R, 2R) -1,2-BIS- (5- (4-Hidroksinaftalin-1- İlazo) - [1, 3,4] Tiyadiazol-2- Diol Yeni Bileşiğinin İn vitro Antioksidan Özellikleri

Year 2018, Volume: 39 Issue: 3, 658 - 667, 30.09.2018

Akif Evren Parlak , Pelin Koparır

https://doi.org/10.17776/csj.412123
Cited By: 1

Abstract

1,3,4-Tiyadiazoller
yapılarındaki gruplara bağlı olarak çeşitli biyolojik aktivitelere sahiptir. Bu
çalışma, (1R,2R) -l, 2-bis- (5- (4-hidroksinaftalin-1-ilazo) - [l, 3,4]
tiyaiyazol-2-il) etan-1,2-diole yeni bileşiğinin in vitro antioksidan özelliklerini araştırmayı amaçlamaktadır. Bu
çalışmada antioksidan aktiviteler;  DPPH. radikal temizleme aktivitesi, demir azaltma
gücü kapasitesi, metal şelatlama aktivitesi ve hidroksil radikali temizleme
aktivitesi gibi farklı yöntemlerle ölçüldü Sonuç olarak, bu yeni bileşiğin BHT
ve α -tokoferol gibi referans antioksidanlar ile karşılaştırıldığında etkili
antioksidan ve serbest radikal süpürücü aktiviteye sahip olduğu belirlendi.

Keywords

1-3-4 tiadiazol antioksidan aktivite radikal süpürücü aktivite biyolojik aktiviteler

References

  • [1]. Genestra M., Oxyl radicals, redox-sensitive signalling cascades and antioxidants, Cell Signal, 19(9) (2007) 1807-1819.
  • [2]. Bagchi D., Bagchi M., Stohs S.J., Das D.K., Ray S.D., Kuszynski C.A., Joshi S.S, Pruess H.G., Free radicals and grape seed proanthocyanidin extract: Importance in human health and disease prevention, Toxicology, 148 (2000) 187-197.
  • [3]. Datta K., Sinha S., Chattopadhyay P., Reactive oxygen species in health and disease. Natl Med J India., 13 (2000) 304-10.
  • [4]. Blois M. S., Antioxidant determinations by the use of a stable free radical. Nature, 26 (1958) 1119-1200.
  • [5]. Nagar R., Syntheses, characterization, and microbial activity of some transition metal complexes involving potentially active O and N donor heterocyclic ligands. J Inorg Biochem., 40 (1990) 349-356.
  • [6]. Cavigiolioa G., Benedettoa L., Boccaleria E., Colangelob D., Vianob I., Osellac D., Pt[II] complexes with different N-donor aromatic ligands for specific inhibition of telmerase. Inorg Chim Acta., 305 (2000) 61-68.
  • [7]. Pires dos Santos M.L., Alairo A.F., Mangrich, A.S., Ferreira A.M.C., Antioxidant and Prooxidant Properties of some di-Schiff Base Copper(II) Complexes. J. of Inorg. Biochem. 71 (1998)71-78.
  • [8]. İkizler A., Hetero halkalı Bileşikler, Karadeniz Teknik Üniversitesi Fen-Edebiyat Fakültesi, (1985).Genel Yayın No: 84, Fakülte Yayın No: 38, Trabzon, 225-231, 243-245
  • [9]. Chapleo C.B., Myers M., Myers P.L., Saville J.F., Smith A.C.B., Stillings M.R., Tulloch I.F., Walter D.S., Welbourn A.P., Substituted 1,3,4-thiadiazoles with anticonvulsant activity. J Med Chem, 29 (1986) 2273-2280.
  • [10]. Palaska E., Şahin G., Kelicen P., Durlu N.T., Altinok G., Synthesis and antiinflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and l,2,4-triazole-3-thiones. Farmaco, 57 (2002) 101-110.
  • [11]. Gawande N.G., Shingare M.S., Synthesis of some thiazolyl-thiosemicarbazides, triazoles, oxadiazoles, thiadiazoles and their microbial activity, Ind J Chem, 26 (1987) 387-389.
  • [12]. Patel H.V., Fernandes P.S., Synthesis and biological activities of some substituted pyrazolylmethylene-1,2,4-triazoles, -1,3,4-thiadiazoles and -1,3,4-oxadiazoles., J Ind Chem Soc, 67 (1990) 401-403.
  • [13]. Oral B., Rollas S., The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5-one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety, Marmara Pharm J, 16 (2012) 222-228.
  • [14]. Turner S., Myers M., Gadie B., Hale S.A., Horsley A., Nelson A.J., Pape R, Saville J.F., Doxey J.C., Berridge T.L., Antihypertensive thiadiazoles. 2. Vasodilator activity of some 2-aryl-5-guanidino-l,3,4-thiadiazoles with., J Med Chem, 31 (1988) 906- 913.
  • [15]. Mhasalkar M.Y., Shah M.H., Nikam S.T., Further studies in substituted 4H-1,2,4-Triazoles for Possible Hypoglycemic Activity. J Med Chem, 14(3) (1970) 260-262.
  • [16]. Rzeski W., Matysiak J., Szerszen M.K., Anticancer, neuroprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound., Bioorg Med Chem, 15 (2007) 3201-3207.
  • [17]. Ulusoy-Güzeldemirci N., Küçükbasmacı Ö., Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety, Eur J Med Chem, 45 (2010) 63-68.
  • [18]. Koparir M,. Cansiz A,. Cetin A, and Kazaz C., Synthesıs Of (1R,2R)-1,2-Bıs-(5-(4-Hydroxynaphthalen-1-Ylazo)- [1,3,4]Thıadıazol-2-Yl)-Ethane-1,2-Dıol, Chemistry of Natural Compounds, 41(5)(2005) .
  • [19]. Dinis T.C.P, Madeira V.M.C., Almeida L.M., Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers, Arch. Biochem. Biophys., 315 (1994) 161–169.
  • [20]. Oyaizu M., Studies on products of browning reaction prepared from glucosamine, Jpn. Nutr. 44 (1986) 307–316.
  • [21]. Halliwell B., Gutteridge J. M. C., Aruoma, O. I., The deoxyribose method: a simple test-tube assay for determination of rate constants for reactions of hydroxyl radicals, Analytical Biochemistry, 165 (1987) 215–219.
  • [22]. Edwin N.F., Huang S.W., Kanner J., Bruce German, J., Interfacial phenomena in the evaluation of antioxidants: bulk oils versus emulsions. J Agric Food Chem., 42(1994) 1054-1059.
  • [23]. Kolevai I.I., Van Beek T.A., Linssen J.P., De Groot A., Evstatieva L.N., Screening of plant extracts for antioxidant activity: a comparative study on three testing methods., Phytochem Anal., 13 (2002) 8-17.
  • [24]. Macdonald-Wicks L.K., Wood L.G., Garg M.L., Methodology For The Determination Of Biological Antioxidant Capacity İn Vitro: A Review. J Sci Food Agric., 86 (2006) 2046-2056.
  • [25]. Scalzo R.L., Organic Acids İnfluence on DPPH Scavenging By Ascorbic Acid. Food Chem. 107 (2008) 40-43.
  • [26]. Meir S., Kanner J., Akiri B., Hadas S.P., Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves,J. Agri. Food. Chem., 43 (1995) 1813.
  • [27]. Chung Y.C., Chang C.T., Chao W.W., Lin C.F, Chou S.T., Antioxidative activity and safety of the 50% ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1,J. Agric. Food Chem., 50 (2002) 2454.
  • [28]. Yildirim A., Mavi A., Kara A.A., Determination of antioxidant and antimicrobial activities of Rumexcrispus L. extracts,J. Agri. Food. Chem. 49 (2001) 4083.
  • [29]. Yamaguchi F., Ariga T,. Yoshimira Y, Nakazawa H., Antioxidative and anti-glycation activity of garcinol from garciniaindica fruit rind, Journal of Agricultural and Food Chemistry, 48 (2000) 180.
  • [30]. Finefrock A. E., Bush A. I., Doraiswamy P. M., Current status of metals as therapeutic targets in Alzheimer’s disease, Journal of the American Geriatrics Society., 51 (2003) 1143.
  • [31]. Çiftci S.Y., Kelekçi N.G., Gökşen U.S., Uçar G., Free-Radical Scavenging Activities of 2-Benzoxazolinone Derivatives Containing Thiosemicarbazide, Triazole, Thiadiazole and Hydrazone Units, Hacettepe University Journal of the Faculty of Pharmacy, 31 (2011) 27-50.
  • [32]. Kulisic T., Radonic A., Katalinic V., Milos M., Use of different methods for testing antioxidative activity of oregano essential oil. Food Chem., 85 (2004) 633-640.

In vıtro Antioxidant Properties of Novel Compound (1R, 2R) -1,2-bis- (5- (4- Hydroxynaphthalen-1-ylazo) - [1,3,4] Thiadiazol-2-YL) -Ethane- 1,2-Diole

Year 2018, Volume: 39 Issue: 3, 658 - 667, 30.09.2018

Akif Evren Parlak , Pelin Koparır

https://doi.org/10.17776/csj.412123
Cited By: 1

Abstract

1,3,4-Thiadiazoles have a variety of biological
activities depending on their substituents. This study aims to investigate
the in vitro antioxidant properties of 1R,2R
-1,2-bis- (5- (4-hydroxynaphthalen-1-ylazo) - [1,3,4] thiadiazol-2-yl) -ethane- 1,2-diole novel
compound.  In this study, antioxidant activities were measured by different methods
such as, DPPH. radical scavenging activity, iron reducing
power capacity, metal chelating activity and hydroxyl radical scavenging
activity. As a result, it was determined that this new compound has effective
antioxidant and free radical scavenging activity when compared to reference
antioxidants such as BHT and α-tocopherol.

Keywords

antioxidant activity radical scavenging activity 1-3-4 Thiadiazol biological activities biological activities

References

  • [1]. Genestra M., Oxyl radicals, redox-sensitive signalling cascades and antioxidants, Cell Signal, 19(9) (2007) 1807-1819.
  • [2]. Bagchi D., Bagchi M., Stohs S.J., Das D.K., Ray S.D., Kuszynski C.A., Joshi S.S, Pruess H.G., Free radicals and grape seed proanthocyanidin extract: Importance in human health and disease prevention, Toxicology, 148 (2000) 187-197.
  • [3]. Datta K., Sinha S., Chattopadhyay P., Reactive oxygen species in health and disease. Natl Med J India., 13 (2000) 304-10.
  • [4]. Blois M. S., Antioxidant determinations by the use of a stable free radical. Nature, 26 (1958) 1119-1200.
  • [5]. Nagar R., Syntheses, characterization, and microbial activity of some transition metal complexes involving potentially active O and N donor heterocyclic ligands. J Inorg Biochem., 40 (1990) 349-356.
  • [6]. Cavigiolioa G., Benedettoa L., Boccaleria E., Colangelob D., Vianob I., Osellac D., Pt[II] complexes with different N-donor aromatic ligands for specific inhibition of telmerase. Inorg Chim Acta., 305 (2000) 61-68.
  • [7]. Pires dos Santos M.L., Alairo A.F., Mangrich, A.S., Ferreira A.M.C., Antioxidant and Prooxidant Properties of some di-Schiff Base Copper(II) Complexes. J. of Inorg. Biochem. 71 (1998)71-78.
  • [8]. İkizler A., Hetero halkalı Bileşikler, Karadeniz Teknik Üniversitesi Fen-Edebiyat Fakültesi, (1985).Genel Yayın No: 84, Fakülte Yayın No: 38, Trabzon, 225-231, 243-245
  • [9]. Chapleo C.B., Myers M., Myers P.L., Saville J.F., Smith A.C.B., Stillings M.R., Tulloch I.F., Walter D.S., Welbourn A.P., Substituted 1,3,4-thiadiazoles with anticonvulsant activity. J Med Chem, 29 (1986) 2273-2280.
  • [10]. Palaska E., Şahin G., Kelicen P., Durlu N.T., Altinok G., Synthesis and antiinflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and l,2,4-triazole-3-thiones. Farmaco, 57 (2002) 101-110.
  • [11]. Gawande N.G., Shingare M.S., Synthesis of some thiazolyl-thiosemicarbazides, triazoles, oxadiazoles, thiadiazoles and their microbial activity, Ind J Chem, 26 (1987) 387-389.
  • [12]. Patel H.V., Fernandes P.S., Synthesis and biological activities of some substituted pyrazolylmethylene-1,2,4-triazoles, -1,3,4-thiadiazoles and -1,3,4-oxadiazoles., J Ind Chem Soc, 67 (1990) 401-403.
  • [13]. Oral B., Rollas S., The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5-one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety, Marmara Pharm J, 16 (2012) 222-228.
  • [14]. Turner S., Myers M., Gadie B., Hale S.A., Horsley A., Nelson A.J., Pape R, Saville J.F., Doxey J.C., Berridge T.L., Antihypertensive thiadiazoles. 2. Vasodilator activity of some 2-aryl-5-guanidino-l,3,4-thiadiazoles with., J Med Chem, 31 (1988) 906- 913.
  • [15]. Mhasalkar M.Y., Shah M.H., Nikam S.T., Further studies in substituted 4H-1,2,4-Triazoles for Possible Hypoglycemic Activity. J Med Chem, 14(3) (1970) 260-262.
  • [16]. Rzeski W., Matysiak J., Szerszen M.K., Anticancer, neuroprotective activities and computational studies of 2-amino-1,3,4-thiadiazole based compound., Bioorg Med Chem, 15 (2007) 3201-3207.
  • [17]. Ulusoy-Güzeldemirci N., Küçükbasmacı Ö., Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety, Eur J Med Chem, 45 (2010) 63-68.
  • [18]. Koparir M,. Cansiz A,. Cetin A, and Kazaz C., Synthesıs Of (1R,2R)-1,2-Bıs-(5-(4-Hydroxynaphthalen-1-Ylazo)- [1,3,4]Thıadıazol-2-Yl)-Ethane-1,2-Dıol, Chemistry of Natural Compounds, 41(5)(2005) .
  • [19]. Dinis T.C.P, Madeira V.M.C., Almeida L.M., Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers, Arch. Biochem. Biophys., 315 (1994) 161–169.
  • [20]. Oyaizu M., Studies on products of browning reaction prepared from glucosamine, Jpn. Nutr. 44 (1986) 307–316.
  • [21]. Halliwell B., Gutteridge J. M. C., Aruoma, O. I., The deoxyribose method: a simple test-tube assay for determination of rate constants for reactions of hydroxyl radicals, Analytical Biochemistry, 165 (1987) 215–219.
  • [22]. Edwin N.F., Huang S.W., Kanner J., Bruce German, J., Interfacial phenomena in the evaluation of antioxidants: bulk oils versus emulsions. J Agric Food Chem., 42(1994) 1054-1059.
  • [23]. Kolevai I.I., Van Beek T.A., Linssen J.P., De Groot A., Evstatieva L.N., Screening of plant extracts for antioxidant activity: a comparative study on three testing methods., Phytochem Anal., 13 (2002) 8-17.
  • [24]. Macdonald-Wicks L.K., Wood L.G., Garg M.L., Methodology For The Determination Of Biological Antioxidant Capacity İn Vitro: A Review. J Sci Food Agric., 86 (2006) 2046-2056.
  • [25]. Scalzo R.L., Organic Acids İnfluence on DPPH Scavenging By Ascorbic Acid. Food Chem. 107 (2008) 40-43.
  • [26]. Meir S., Kanner J., Akiri B., Hadas S.P., Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves,J. Agri. Food. Chem., 43 (1995) 1813.
  • [27]. Chung Y.C., Chang C.T., Chao W.W., Lin C.F, Chou S.T., Antioxidative activity and safety of the 50% ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1,J. Agric. Food Chem., 50 (2002) 2454.
  • [28]. Yildirim A., Mavi A., Kara A.A., Determination of antioxidant and antimicrobial activities of Rumexcrispus L. extracts,J. Agri. Food. Chem. 49 (2001) 4083.
  • [29]. Yamaguchi F., Ariga T,. Yoshimira Y, Nakazawa H., Antioxidative and anti-glycation activity of garcinol from garciniaindica fruit rind, Journal of Agricultural and Food Chemistry, 48 (2000) 180.
  • [30]. Finefrock A. E., Bush A. I., Doraiswamy P. M., Current status of metals as therapeutic targets in Alzheimer’s disease, Journal of the American Geriatrics Society., 51 (2003) 1143.
  • [31]. Çiftci S.Y., Kelekçi N.G., Gökşen U.S., Uçar G., Free-Radical Scavenging Activities of 2-Benzoxazolinone Derivatives Containing Thiosemicarbazide, Triazole, Thiadiazole and Hydrazone Units, Hacettepe University Journal of the Faculty of Pharmacy, 31 (2011) 27-50.
  • [32]. Kulisic T., Radonic A., Katalinic V., Milos M., Use of different methods for testing antioxidative activity of oregano essential oil. Food Chem., 85 (2004) 633-640.
There are 32 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Akif Evren Parlak

Pelin Koparır

Publication Date September 30, 2018
Submission Date April 3, 2018
Acceptance Date May 22, 2018
Published in Issue Year 2018Volume: 39 Issue: 3

Cite

APA Parlak, A. E., & Koparır, P. (2018). In vıtro Antioxidant Properties of Novel Compound (1R, 2R) -1,2-bis- (5- (4- Hydroxynaphthalen-1-ylazo) - [1,3,4] Thiadiazol-2-YL) -Ethane- 1,2-Diole. Cumhuriyet Science Journal, 39(3), 658-667. https://doi.org/10.17776/csj.412123

Cited By

Novel Bis-1,3,4-Thiadiazoles Derivatives: Synthesis, Spectroscopic Characterization, DFT Calculations and Evaluation of their Antimicrobial and Antioxidant Activities
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