Schiff base derivatives with morpholine and antioxidant activity

Year 2019, Volume: 1 Issue: 1, - , 11.12.2019

Dilek Ünlüer Ersan Bektaş Yasemin Ünver

Abstract

New Schiff base derivatives with morpholines, 4-bromo-2-(((4-morpholinophenyl)imino)methyl)phenol
(I) and 4-bromo-2-(((2-morpholinoethyl) imino) methyl)phenol (II)   were synthezised. The compounds I-
II were characterized by spectral methods IR, and NMR spectroscopic techniques. Antioxidant activities of compounds I and
II were determined by the
ferric reducing ability of plasma (FRAP) assay method which is based on the reduction of Fe3+
-TPTZ complex to the Fe2+ -TPTZ complex in the presence of antioxidants. Compound
I has relatively high ferric reducing power ability (i.e., antioxidant
activity) than compound II. The
ability of compound I and II to reduce iron (III) to iron (II) ions were calculated as 929 and
11 µM FeSO₄.7H₂O equivalent/g sample, respectively.To summarize, the above-mentioned results indicate
that compound II has inefficient antioxidant
activity and Compound I has
effective antioxidant activity.

Keywords

Schiff base, Morpholine, Antioxidant Activity

References

• [1] Liu. Z., Wang, B., Yang, Z., Li, Y., Qin, D., Li, T. 2009. “Synthesis, crystal structure, DNA interaction and antioxidant activities of two novel water-soluble Cu(2þ) complexes derivated from 2-oxo-quinoline-3- carbaldehyde Schiff-bases“, Eur J Med Chem. 44, 4477-4484.
• [2] Hussain, H., Babic, G., Durst, T., Wright, J., Flueraru, M., Chichirau, A., Chepelev, L.L.2003. “Development of Novel Antioxidants:  Design, Synthesis, and Reactivity“, Org. Chem. 6, 7023-7032.
• [3] Ünver, Y., Sancak, K., Çelik, F., Birinci, E., Küçük, M., Soylu, S., Burnaz, N. A. 2014. “New thiophene-1,2,4-triazole-5(3)-ones: highly bioactive thiosemicarbazides, structures of schiff bases and triazole-thiols“, European Journal of Medicinal Chemistry 84, 639-650.
• [4] Ünver, Y., Deniz, S., Çelik, F., Akar, Z., Küçük, M., Sancak, K. 2016. “Synthesis of New 1,2,4-Triazole Compounds Containing Schiff and Mannich Bases (Morpholine) with Antioxidant and Antimicrobial Activities“, Journal of Enzym İnhibition and Medicinal Chemistry 31(3S), 89-95.
• [5] Ünver, Y., Bektaş, E. 2018. “Synthesis and biological activity of new Schiff bases of benzylideneamine bearing thiophene, 1,2,4-triazolone, 1,3,4-oxadiazole, morpholine moieties“, Letters in Drug Design & Discovery 15, 706-712.
• [6] Ünver, Y., Bektaş, E., Direkel, Ş. 2018. “Synthesis And Antioxidant And Antileishmanial Activities of New Bis N-Amino Triazole Derivatives“, Russian Journal of General Chemistry 88, 2616-2620.
• [7] Ünver, Y., Tuluk, M., Kahriman, N., Emirik,E., Bektaş, E., Direkel, Ş. 2019. “New Chalcone Derivatives With Schiff Base-Thiophene: Synthesis, Biological Activity And Molecular Docking Studies“, Russian Journal of General Chemistry 89, 794-799.
• [8] Ünver, Y., Baş, H., Bıyıklıoğlu, Z. 2019. “Non-peripherally 4-{[(1E)-1-benzothien-2-ylmethylene]amino} phenol substituted zinc(II), manganese(III), cobalt(II) phthalocyanines:Synthesis and electrochemistry“, Journal of Molecular Structure 1178, 508-513.
• [9] Serbest, K., Özen, A., Ünver, Y., Er, M., Değirmencioğlu, İ., Sancak, K. 2009. “Spectroscopic and theoretical study of 1,2,4-triazole-3-one based salicyaldimine complexes and evaluation of superoxide-scavenging propertie“, Journal of Molecular Structure 922, 1-10.
• [10] Serbest, K., Değirmencioğlu, İ., Ünver, Y., Er, M., Kantar, C., Sancak, K. 2007. “Microwave-assisted synthesis and characterization and theorical calculations of the first example of free and metalo phthalocyanines from salen type Schiff base derivative bearing thiophen and triazole heterocyclic ring“, Journal of Organometallic Chemistry 692, 5646-5654.
• [11] Avramova, P., Danchev, N., Buyukliev, R., Bogoslovova, T. 1998. “Synthesis, Toxicological, and Pharmacological Assessment of Derivatives of 2-Aryl-4-(3-arylpropyl)morpholines“, Arch Pharm. 331:342–346.
• [12] Dhahagani, K.; Mathan Kumar, S.; Chakkaravarthi, G.; Anitha, K.; Rajesh, J.; Ramu, A.; Rajagopal, G. 2014. “Synthesis and spectral characterization of Schiff base complexes of Cu(II), Co(II), Zn(II) and VO(IV) containing 4-(4-aminophenyl)morpholine derivatives: Antimicrobial evaluation and anticancer studies“.Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy 117, 87-94.
• [13] Benzie I.F.F., Szeto, Y.T. 1999. “Total Antioxidant Capacity of Teas by the Ferric Reducing/Antioxidant Power Assay“, J. Agric. Food Chem. 47(2), 633–636.