Research Article
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Year 2017, , 32 - 49, 01.06.2017
https://doi.org/10.5281/zenodo.3768580

Abstract

References

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  • [2] E. Hensler Mary, G. Bernstein, V. Nizet, A. Nefzi, Pyrrolidine bis-cyclic guanidines with antimicrobial activity against drug-resistant Gram-positive pathogens identified from a mixture-based combinatorial library, Bioorg Med Chem Lett, 16 (2006) 5073-5079
  • [3] X. Li, Y. Li, W. Xu, Design, synthesis, and evaluation of novel galloyl pyrrolidine derivatives as potential anti-tumor agents, Bioorg Med Chem, 14 (2006) 1287-1293
  • [4] J. Obniska, A. Zagorska, Synthesis and anticonvulsant properties of new N-[(4- arylpiperazin-1-yl)-methyl] derivatives of 3-aryl pyrrolidine-2,5-dione and 2- azaspiro[4.4]nonane-1,3-dione, Il Farmaco, 58 (2003) 1227-1234
  • [5] S. Imamura, Y. Ishihara, T. Hattori, O. Kurasawa, Y. Matsushita, Y. Sugihara, N. Kanzaki, Y. Lizawa, M. Baba, S. Hashiquchi, CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biological evaluation of 5-oxopyrrolidine-3-carboxamide derivatives, Chem Pharm Bull, 52 (2004) 63-73
  • [6] F.E. Onen-Bayram, I. Durmaz, D. Scherman, J. Herscovici, R. Cetin- Atalay, A novel thiazolidine compound induces caspase-9 dependent apoptosis in cancer cells, Bioorg Med Chem, 20 (2012) 5094-5102
  • [7] F.E. Onen-Bayram, K. Buran, I. Durmaz, B. Berk, R. Çetin-Atalay, 3-Propionylthiazolidine-4-carboxylic acid ethyl esters: a family of antiproliferative thiazolidines, Med Chem Commun, 6 (2015) 90-93
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  • [9] N.F. Pavin, F. Donato, F.W. Cibin, C.R. Jesse, P.H. Schneider, H.D. De Salles, L.D.A. Soares, D. Alves, L. Savegnago, Antinociceptive and anti-hypernociceptive effects of Sephenyl thiazolidine-4-carboselenoate in mice, Eur J Pharmacol, 668 (2011) 169-176
  • [10] L. Del Fabbro, C. Borges Filho, L. Cattelan Souza, L. Savegnago, D. Alves, P. Henrique Schneider, H.D. de Salles, C.R. Jesse, Effects of Se-phenyl thiazolidine-4-carboselenoate on mechanical and thermal hyperalgesia in brachial plexus avulsion in mice: mediation by cannabinoid CB1 and CB2 receptors, Brain Res 1475 (2012) 31-6
  • [11] N.V. Francine, M.M. Débora, C. Micheli, M.C. Angela, A. Diego, JL. Eder, D.S. Salles, H.S. Paulo, S. Lucielli, Antioxidant properties of (R)-Se-aryl thiazolidine-4- carboselenoate, Chem Biol Interact. 205 (2013) 100-107
  • [12] O. Rosati, M. Curini, M.C. Marcotullio, A. Macchiarulo, M. Perfumi, L. Mattioli, F. Rismondo, G. Cravotto, Synthesis, docking studies and anti-inflammatory activity of 4,5,6,7-tetrahydro-2H-indazole derivatives, Bioorg Med Chem, 15 (2007) 3463-3473
  • [13] E. Banoğlu, C. Akoğlu, S. Unlu, E. Küpeli, E. Yesilada, M.F. Şahin, Amide derivatives of [6-(5-methyl-3-phenylpyrazole-1-yl)-3(2H)-pyridazinone-2-yl]acetic acids as potential analgesic and anti-inflammatory compounds. Arch Pharm Pharm Med Chem, 337 (2004) 7-14
  • [14] N. Benaamane, B. Nedjar-Kolli, Y. Bentarzi, L. Hammal, A. Geronikaki, P. Eleftheriou, A. Lagunin, Synthesis and in silico biological activity evaluation of new N-substituted pyrazolo-oxazin-2-one systems, Bioorg Med Chem, 6 (2008) 3059-3066
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  • [17] L. Vomos-Vigyazo, Polyphenol oxidase and peroxidase in fruits and vegetables, Crit Rev Food Sci Nutr, 15 (1981) 49-127
  • [18] K.G. Strothkemp, R.L. Jolley, H.S. Mason, Quaternary structure of mushroom tyrosinase, Biochem Biophys Res Commun, 70 (1976) 519-524
  • [19] I. Parveen, M.D. Threadgill, J.M. Moorby, A. Winters, Oxidative phenols in forage crops containing polyphenol oxidase enzymes, J Agric Food Chem, 58 (2010) 1371-1382
  • [20] M. Seiberg, C. Paine, E. Sharlow, P. Andrade-Gordun, M. Costanzo, M. Eisinger, S.S. Shapiro, Inhibition of melanosome transfer results in skin lightening, J Invest Dermatol, 115 (2000)162-167
  • [21] L.A. Nguyen, H. He, Chuong, Pham-Huy, Chiral Drugs: An overview, Int J Biomed Sci, 2 (2006) 85-100
  • [22] A. Verma, S.K. Saraf, 4-Thiazolidinone - a biologically active scaffold, Eur J Med Chem, 43 (2008) 897-905
  • [23] M.R. Shaaban, A.S. Mayhoub, A.M. Farag, Recent advances in the therapeutic applications of pyrazolines, Expert Opin Ther Pat, 22 (2012) 253-291
  • [24] S. Khatib, O. Nerya, R. Musa, M. Shumel, S. Tamir, J. Vaya, Chalcones as Potent Tyrosinase Inhibitors: The Importance of 2,4-disubstituted Resorcinol Moiety, Bioorg Med Chem, 13 (13) 433-441
  • [25] G. Bruno, L. Costantino, C. Curinga, R. Maccari, F. Monforte, F. Nicolo, R. Ottana, M.G. Vigorita, Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4- thiazolidinediones, Bioorg Med Chem, 10 (2002) 1077-1084
  • [26] D. Pandey, A.K. Nag, Synthesis of Some Thiazolidinopyrazolines from Rhodanine, Asian Journal of Chemistry, 12 (2000) 612-614
  • [27] M.W. Weatherburn, Phenol-hypochlorite reaction for determination of ammonia, Anal Chem, 3 (1967) 971-4

SYNTHESIS, CHARACTERIZATION, UREASE INHIBITORY AND TYROSINASE INHIBITORY ACTIVITIES OF SOME CHIRAL PYRAZOLO DERIVATIVES

Year 2017, , 32 - 49, 01.06.2017
https://doi.org/10.5281/zenodo.3768580

Abstract

A series of some pyrazolo derivatives a-f were synthesized and their urease inhibitory and tyrosinase inhibitory activities were evaluated. Among synthesized compounds, 2f, 2e, 1f, 2d, 1e, 2b, and 1d showed excellent activities IC50 i.e. 11.73±0.28, 14.21±0.56, 15.37±0.89, 17.66±0.82, 18.64±0.19, 19.55±0.39, and 22.08±0.96 µM, respectively. According to tyrosinase assay results, compound 2f showed the good tyrosinase inhibitory activity i.e. 6.12±0.40 mM of IC50

References

  • [1] F. Bellina, R. Rossi, Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions, Tetrahedron, 62 (2006) 7213
  • [2] E. Hensler Mary, G. Bernstein, V. Nizet, A. Nefzi, Pyrrolidine bis-cyclic guanidines with antimicrobial activity against drug-resistant Gram-positive pathogens identified from a mixture-based combinatorial library, Bioorg Med Chem Lett, 16 (2006) 5073-5079
  • [3] X. Li, Y. Li, W. Xu, Design, synthesis, and evaluation of novel galloyl pyrrolidine derivatives as potential anti-tumor agents, Bioorg Med Chem, 14 (2006) 1287-1293
  • [4] J. Obniska, A. Zagorska, Synthesis and anticonvulsant properties of new N-[(4- arylpiperazin-1-yl)-methyl] derivatives of 3-aryl pyrrolidine-2,5-dione and 2- azaspiro[4.4]nonane-1,3-dione, Il Farmaco, 58 (2003) 1227-1234
  • [5] S. Imamura, Y. Ishihara, T. Hattori, O. Kurasawa, Y. Matsushita, Y. Sugihara, N. Kanzaki, Y. Lizawa, M. Baba, S. Hashiquchi, CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biological evaluation of 5-oxopyrrolidine-3-carboxamide derivatives, Chem Pharm Bull, 52 (2004) 63-73
  • [6] F.E. Onen-Bayram, I. Durmaz, D. Scherman, J. Herscovici, R. Cetin- Atalay, A novel thiazolidine compound induces caspase-9 dependent apoptosis in cancer cells, Bioorg Med Chem, 20 (2012) 5094-5102
  • [7] F.E. Onen-Bayram, K. Buran, I. Durmaz, B. Berk, R. Çetin-Atalay, 3-Propionylthiazolidine-4-carboxylic acid ethyl esters: a family of antiproliferative thiazolidines, Med Chem Commun, 6 (2015) 90-93
  • [8] P. Prabhakar, H.S. Thatte, R.M. Goetz, M.R. Cho, D.E. Golan, T. Michel, Receptorregulated translocation of endothelial nitric-oxide synthase, J Biol Chem 273 (1998) 27383-27388
  • [9] N.F. Pavin, F. Donato, F.W. Cibin, C.R. Jesse, P.H. Schneider, H.D. De Salles, L.D.A. Soares, D. Alves, L. Savegnago, Antinociceptive and anti-hypernociceptive effects of Sephenyl thiazolidine-4-carboselenoate in mice, Eur J Pharmacol, 668 (2011) 169-176
  • [10] L. Del Fabbro, C. Borges Filho, L. Cattelan Souza, L. Savegnago, D. Alves, P. Henrique Schneider, H.D. de Salles, C.R. Jesse, Effects of Se-phenyl thiazolidine-4-carboselenoate on mechanical and thermal hyperalgesia in brachial plexus avulsion in mice: mediation by cannabinoid CB1 and CB2 receptors, Brain Res 1475 (2012) 31-6
  • [11] N.V. Francine, M.M. Débora, C. Micheli, M.C. Angela, A. Diego, JL. Eder, D.S. Salles, H.S. Paulo, S. Lucielli, Antioxidant properties of (R)-Se-aryl thiazolidine-4- carboselenoate, Chem Biol Interact. 205 (2013) 100-107
  • [12] O. Rosati, M. Curini, M.C. Marcotullio, A. Macchiarulo, M. Perfumi, L. Mattioli, F. Rismondo, G. Cravotto, Synthesis, docking studies and anti-inflammatory activity of 4,5,6,7-tetrahydro-2H-indazole derivatives, Bioorg Med Chem, 15 (2007) 3463-3473
  • [13] E. Banoğlu, C. Akoğlu, S. Unlu, E. Küpeli, E. Yesilada, M.F. Şahin, Amide derivatives of [6-(5-methyl-3-phenylpyrazole-1-yl)-3(2H)-pyridazinone-2-yl]acetic acids as potential analgesic and anti-inflammatory compounds. Arch Pharm Pharm Med Chem, 337 (2004) 7-14
  • [14] N. Benaamane, B. Nedjar-Kolli, Y. Bentarzi, L. Hammal, A. Geronikaki, P. Eleftheriou, A. Lagunin, Synthesis and in silico biological activity evaluation of new N-substituted pyrazolo-oxazin-2-one systems, Bioorg Med Chem, 6 (2008) 3059-3066
  • [15] Z. Amtul, R. Atta-ur., R.A. Siddiqui, M.I. Choudhary, Chemistry and mechanisim of urease inhibition. Curr Med Chem, 9 (2002) 1323-1348
  • [16] L.V. Modolo, A.X. Souza, L.P. Horta, D.P. Araujo, A. Fátima, An overview on the potential of natural products as ureases inhibors: a review, J Adv Res, 6 (2015) 35-44
  • [17] L. Vomos-Vigyazo, Polyphenol oxidase and peroxidase in fruits and vegetables, Crit Rev Food Sci Nutr, 15 (1981) 49-127
  • [18] K.G. Strothkemp, R.L. Jolley, H.S. Mason, Quaternary structure of mushroom tyrosinase, Biochem Biophys Res Commun, 70 (1976) 519-524
  • [19] I. Parveen, M.D. Threadgill, J.M. Moorby, A. Winters, Oxidative phenols in forage crops containing polyphenol oxidase enzymes, J Agric Food Chem, 58 (2010) 1371-1382
  • [20] M. Seiberg, C. Paine, E. Sharlow, P. Andrade-Gordun, M. Costanzo, M. Eisinger, S.S. Shapiro, Inhibition of melanosome transfer results in skin lightening, J Invest Dermatol, 115 (2000)162-167
  • [21] L.A. Nguyen, H. He, Chuong, Pham-Huy, Chiral Drugs: An overview, Int J Biomed Sci, 2 (2006) 85-100
  • [22] A. Verma, S.K. Saraf, 4-Thiazolidinone - a biologically active scaffold, Eur J Med Chem, 43 (2008) 897-905
  • [23] M.R. Shaaban, A.S. Mayhoub, A.M. Farag, Recent advances in the therapeutic applications of pyrazolines, Expert Opin Ther Pat, 22 (2012) 253-291
  • [24] S. Khatib, O. Nerya, R. Musa, M. Shumel, S. Tamir, J. Vaya, Chalcones as Potent Tyrosinase Inhibitors: The Importance of 2,4-disubstituted Resorcinol Moiety, Bioorg Med Chem, 13 (13) 433-441
  • [25] G. Bruno, L. Costantino, C. Curinga, R. Maccari, F. Monforte, F. Nicolo, R. Ottana, M.G. Vigorita, Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4- thiazolidinediones, Bioorg Med Chem, 10 (2002) 1077-1084
  • [26] D. Pandey, A.K. Nag, Synthesis of Some Thiazolidinopyrazolines from Rhodanine, Asian Journal of Chemistry, 12 (2000) 612-614
  • [27] M.W. Weatherburn, Phenol-hypochlorite reaction for determination of ammonia, Anal Chem, 3 (1967) 971-4
There are 27 citations in total.

Details

Primary Language English
Subjects Organic Chemistry
Journal Section Research Article
Authors

Yusuf Sıcak This is me

Said Nadeem This is me

Bedriye Seda Kurşun Aktar This is me

Emine Elçin Oruç Emre This is me

Mehmet Öztürk This is me

Ayşegül Karaküçük İyidoğan This is me

Mehmet Ali Özler This is me

İbrahim Demirtaş This is me

Publication Date June 1, 2017
Published in Issue Year 2017

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