Kadir DOGANAY1, Merve Goksin KARAASLAN2, Burhan ATES2, Aliye ALTUNDAS1,

Year 2016, Volume: 29 Issue: 2, 317 - 321, 20.06.2016

Aliye Altundas Kadir Doğanay Merve Göksin Karaaslan Burhan Ates

Abstract

SYNTHESIS AND RADICAL SCAVENGING PROPERTIES OF SELENOPHENYL BENZAMIDE ANOLOGS

Abstract

Free radicals that result from different kinds of oxidative stress have been concerned in a variety of human disorders, from cardiac ischemia to those affecting the central nervous system. So, there is an increasing interest in the development of antioxidant molecules that can protect cells against free radical damages. Sets of tetrasubstituted selenophene amides 4a-e were synthesized by reaction of 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]selenophen-3-carbonitrile (2) with benzoyl chloride derivatives and the structures of the amide derivatives were characterized byMS, ¹H-NMR, ¹³C-NMR and IR spectra. The synthesized compounds (4a-e) were evaluated in terms of in vitro. The antioxidant properties were determined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging properties and IC₅₀ values of the compounds were in the range from 3.794 to 5.644 mg/mL. Compounds 4c and 4e showed predominant radical scavenging activity among the synthesized analogues.

Keywords

Selenophene, Selenopheneyl benzamide, Antioxidant activity

References

• Młochowski J., Kloc K., Lisiak R, Potaczek P., Wójtowicz H., “Developments in the chemistry of selenaheterocyclic compounds of practical importance in synthesis and medicinal biology” Arkivoc, 14-46 (2007) .
• Parnham MJ, Graf E. Pharmacology of synthetic organic selenium compounds. Prog Drug Res 36: 9-47 (1991).
• Mugesh, G.; Singh, H.B. “Synthetic organoselenium compounds as antioxidants: Glutathione peroxidase activity” Chem. Soc. Rev., 29: 347–357 (2000).
• Schewe, T. “Molecular actions of ebselen--an antiinflammatory antioxidant” Gen. Pharmac. 26:1153 (1995).
• Flohe L., Günzler E.A., Schock H.H., “Glutathione peroxidase: A selenoenzyme” FEBS Lett. 32: 132-134(1973).
• Rotruck J.T., Pope A.L., Ganther H.E., Swanson A.B., Hafeman D.G., Hoekstra W.G., “Selenium: biochemical role as a component of glutathione peroxidase” Science 179: 588-590 (1973).
• Mugesh G., du Mont W.W., Sies H., “Chemistry of biologically important synthetic organoselenium compounds” Chem. Rev. 101: 2125-2179(2001).
• White G.A. “Substituted 2-methylbenzanilides and structurally related carboxamides: inhibition of Complex II activity in mitochondria from a wild-type strain and a carboxin-resistant mutant strain of Ustilago maydis” Pesticide Biochemistry and Physiology. 34: 255–276 (1989).
• Yalcin I., Kaymakcioglu B.K., Oren I., Sener E., Temiz O., “Synthesis and microbiological activity of some novel N-(2-hydroxyl-5-substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides as the possible metabolites of antimicrobial active benzoxazoles” Farmaco. 52: 685–689 (1997).
• Prashanth M.K., Madaiah M, Revanasiddappa H.D., Amruthesh K.N., “Synthesis, Characterization, and BSA Binding Studies of Some New Benzamides Related to Schiff Base” ISRN Organic Chemistry 2013: 791591 (2013).
• Halfpenny P.R., Hill R.G., Horwell D.C., Hughes J., Hunter J.C., Johnson S., Rees D.C.,
• “Highly selective kappa-opioid analgesics. 2. Synthesis and structure-activity relationships of novel N-[(2-aminocyclohexyl)aryl]acetamide derivatives.” J Med Chem. 32(7):1620-6 (1989).
• Angell R.M., Atkinson F.L., Brown M. J., Chuang T.T., Christopher J.A., Cichy-Knight M., Dunn A.K., Hightower K.E., Malkakorpi S., Musgrave J.R., Neu M., Rowland P., Shea R.L., Smith J.L., Somers D.O., Thomas S.A., Thompson G., Wang R., “N-(3-Cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amides as potent, selective, inhibitors of JNK2 and JNK3” Bioorg. & Med. Chem. Lett. 17: 1296–1301 (2007).
• Sarı N., Sahin S.Ç., Öğütcü H., Dede Y., Yalcin S., Altundas A., Doganay K., Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 106: 60–67 (2013).
• El-Sawy E.R., Abo-Salem H.M., Abaid M.S., El-Gendy A.E., Mandour A.H., Synthesis and DPPH radical-scavenging effect of novel heterocyclic derivatives of 2-amino-4-(1-benzoylindol-3-yl)selenophene-3-carbonitrile. Egypt. Pharm. J. (NRC), 12: 120–129 (2013).
• Shimada, K., Fujikawa, K., Yahara, K. and Nakamura, T. “Antioxidative properties of xanthan on the autoxidation of soybean oil in cyclodextrin emulsion”, J. Agric. Food Chem. 40: 945–948 (1992).