Synthesis, characterization and anti-inflammatory evaluation of novel derivatives of Trolox with pharmacological alcohol and amines

A Ahmadi

doi:10.4314/bcse.v31i2.14

Abstract

In order to explore the novel anti-inflammatory agents, some novel Trolox derivatives were synthesized and characterized by IR, 1H-NMR, 13C-NMR, mass and elemental analysis. The anti-inflammatory activities of the target compounds were evaluated via the croton oil-induced ear oedema test in Swiss mice. According to screened results, obtained compounds demonstrated considerable anti-inflammatory action. KEY WORDS: Trolox derivatives, Anti-inflammatory agents, Oxidative stress, Croton oil-induced ear oedema test Bull. Chem. Soc. Ethiop. 2017, 31(2), 331-335. DOI: http://dx.doi.org/10.4314/bcse.v31i2.14

Highlights

Inflammation is defined as a complex series of tissue changes that result in pain and fever [1]
The topical anti-inflammatory activity was evaluated as inhibition of the croton oil-induced ear oedema in Swiss mice
The tested compounds and the reference drug were suspended in 0.5% sodium carboxymethyl cellulose (CMC), respectively

Summary

INTRODUCTION

Inflammation is defined as a complex series of tissue changes that result in pain and fever [1]. IR spectra were recorded with a Thermo Nicolet FT-IR (model Nexus-870, Nicolet Instrument Corp, Madison, Wisconsin, USA) spectrometer. The mixture was filtered while it is cold and the crystals were collected to produce compound I and III. White needle crystals; yield 65%, m.p. 104-106 °C; IR (KBr) (cm-1): 3538 (O-H), 1760 (C=O ester); 1H-NMR (CDCl3), δ: 1.71 (s, 3H, 2-CH3), 1.87 (m, 1H, C-3), 2.25, 2.27, 2.36 (3s, 9H, 5-CH3, 7-CH3, 8CH3), 2.65-2.72 (m, 1H, C-3 chroman equatorial), 2.45-2.65 (m, 2H, C-4 chroman), 4.75 (d, 2H, -O-CH2-CH=CH-), 6.25 (dt, 1H, -O-CH2-CH=CH-), 6.62 (d, 1H, -O-CH2-CH=CH-), 7.14-7.30 (m, 5H, ring cinnamyl); 13C-NMR (CDCl3) (ppm): 4.8, 16.3, 22.7, 41.3, 70.3, 75.5, 123.8, 124.1, 126.3, 128.7, 129.1, 132.8, 133.4, 145.1, 149.8, 152.1; Anal. THF was evaporated, the resulting mixture was dissolved in CH2Cl2 (10 mL), successively washed with water, 5% aqueous HCl and NaHCO3 solutions, dried and the re-crystallization was carried out by petroleum ether (60-80 oC). (ppm): 4.8, 16.4, 22.7, 34.2, 35.3, 42.3, 80.3, 85.5, 123.8, 126.3, 128.7, 129.1, 132.8, 133.4, 149.8, 152.1, 179.5; Anal. calcd. for C18H25NΟ3S (335): C 64.45, H 7.51, Ν 4.18; Found: C 63.94, H 7.44, Ν 4.28%; MS: m/z (regulatory intensity): (100), (20.5), (4.4)

Pharmacological methods

RESULTS AND DISCUSSION

CONCLUSION