Abstract
A series of macrocycles containing isoxazoline, dioxazole, and pyrazole were synthesized and characterized by IR, 1H, and 13C NMR, mass spectra, elemental analysis, and X-ray single crystal determination. The antioxidant activity of synthesized compounds was evaluated. One of the compounds exhibits potent DPPH radical scavenging activity, comparable to that of vitamin E.
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Mor S, Preeti P, Narasimhan B (2012) Eur J Med Chem 57:196
Neochoritis CG, Zarganes-Tzitzikas T, Tsoleridis CA, Stephanidou-Stephanatou J, Kontogiorgis CA, Hadjipavlou-Litina DJ, Choli-Papadopoulou TC (2010) J Med Chem 53:8409
Chioua M, Sucunza D, Soriano E, Hadjipavlou-Litina D, Alcázar A, Ayuso I, Oset-Gasque MJ, González MP, Monjas L, Rodríguez-Franco MI, Marco-Contelles J, Samadi A (2012) J Med Chem 55:153
Mowbray CE, Burt C, Corbau R, Gayton S, Hawes M, Perros M, Tran I, Price DA, Quinton FJ, Selby MD, Stupple PA, Webster R, Wood A (2009) Bioorg Med Chem Lett 19:5857
Wyatt PG, Woodhead AJ, Berdini V, Boulstridge JA, Carr MG, Cross DM, Davis DJ, Devine LA, Early TR, Feltell RE, Lewis EJ, Menamin RL, Navarro EF, Brien MA, Reilly M, Reule M, Saxty G, Seavers LA, Smith DM, Squires M, Trewartha G, Walker MT, Woolford AJ (2008) J Med Chem 51:4986
Wickens P, Kluender H, Dixon J, Brennan C, Achebe F, Bacchiocchi A, Bankston D, Bierer D, Brands M, Braun D, Brown MS, Chuang CY, Dumas J, Enyedy I, Hofilena G, Hong Z, Housley T, Jones B, Khire U, Kreiman C, Kumarasinghe E, Lowinger T, Ott-Morgan R, Perkins L, Phillips B, Schoenleber R, Scott WJ, Sheeler R, Redman A, Sun X, Taylor I, Wang L, Wilhelm S, Zhang X, Zhang M, Sullivan E, Carter C, Miglarese M, Levy J (2007) Bioorg Med Chem Lett 17:4378
Paulis T, Hemstapat K, Chen Y, Zhang Y, Saleh S, Alagille D, Baldwin RM, Tamagnan GD, Conn PJ (2006) J Med Chem 49:3332
Raju SK, Stephen MR, Subbu P, Perumal Y (2010) Tetrahedron Asymmetry 21:1315
Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Suzuki K, Ueda T, Terauchi H, Kawasaki M, Nagai K, Wachi M, Yamagishi JI (2004) Bioorg Med Chem 12:5515
Raju RK, Subbu P (2007) Tetrahedron 63:12220
Pabitra KK, Biswajita B, Pulak JB (2006) Tetrahedron Lett 47:7779
Fumiyasu O, Yasuaki O, Masayuki H, Shuji K (2009) Tetrahedron Lett 50:2111
Sobolev AN, Belsky VK, Romm IP, Chernikova YN, Guryanova EN (1985) Acta Crystallogr C41:967
Pauling L (1967) The nature of chemical bond. Cornell University Press, Ithaca
Umile GS, Francesca I, Francesco P, Giuseppe C, Manuela C, Ortensia IP, Nevio P (2009) Biomacromolecules 10:1923
Singh RP, Chidambarak NM, Jayaprakasha GK (2002) J Agric Food Chem 50:81
Irene P, Francesc V, Jaume B, Alfredo R, Nadine F, Jesua SB, Carles C (2002) J Agric Food Chem 50:6882
Shimada K, Fujikawa K, Yahara K, Nakamura T (1992) J Agric Food Chem 40:945
Leong LP, Shui G (2002) Food Chem 76:69
Braca A, Sortino C, Politi M, Morelli I, Mendez J (2002) J Ethnopharmacol 79:379
Halliwell B, Gutteridge JMC, Aruoma OI (1987) Anal Biochem 165:215
Kontogiorgis C, Hadjipavlou-Litina D (2003) J Enzyme Inhib Med Chem 18:63
Becher J, Olesen P, Knudsen N, Toftlund H (1986) Sulfur Lett 4:175
Liu KC, Shelton BR (1980) J Org Chem 45:3915
Xie ZF, Mo XX, Liu FM (2008) J Heterocycl Chem 45:1485
Blessing RHJ (1997) Appl Cryst 30:421
Yüksektepe C, Kan N, Yılmaz I (2006) Acta Cryst E 62:2762
Spek AL (2003) J Appl Cryst 36:7
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We are grateful to Changji University (Grant No. 2012SSQD020 and 2013 YJZD001) for the financial help.
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Zeng, H., Zeng, Y., Geng, L. et al. Synthesis, characterization, and antioxidant activity of pyrazolic macrocycle. Monatsh Chem 146, 199–206 (2015). https://doi.org/10.1007/s00706-014-1298-2
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DOI: https://doi.org/10.1007/s00706-014-1298-2