Synthesis and Topical Antiinflammatory and Antiallergic Activities of Antioxidant o-Aminophenol Derivatives

Abstract

In order to develop novel compounds for topical use possessing antiallergic as well as antiinflammatory activities, a series of o-aminophenol derivatives bearing H1-antihistaminic structures were synthesized and their effects were investigated on lipid peroxidation in rat brain homogenates, antiinflammatory effection arachidonic acid- and 12-O-tetradecanoylphorbol-13- acetate-induced mouse ear edema and antiallergic effect on 48-h homologous passive cutaneous anaphylaxis in rats. Furthermore, the effects of these compounds on delayed-type hypersensitivity reaction in mice were examined. Several N-monosubstituted amino-4-methylphenols were found to exert potent inhibitory activities in all of these assays. Of these compounds, 4m was chosen for further development as AD0261.

Antioxidants and Inflammatory Disease: Synthetic and Natural Antioxidants with Anti-Inflammatory Activity

“…In addition, it was reported that the novel antioxidant MK-447 (2-amino-methyl)-4-tert-butyl-6-iodophenol) ( Fig. 1) inhibits the anti-inflammatory process [55,56,59,60]. During research on the antioxidant activities of various compounds, it was found that 2-(methylamino)-4-methylphenol can prevent lipid peroxi-dation as estimated by the thiobarbituric acid (TBA) method, with an IC 50 value of 0.03 μg/mL.…”

“…Naoki et al reported the synthesis of antioxidant oaminophenol derivatives with topical anti-inflammatory and anti-allergic activities [55]. The compounds were synthesized as shown in Schemes 1 and 2 and were evaluated for their antioxidant activity using the lipid peroxidation TBA method and for anti-inflammatory properties using the model of TPA-induced edema.…”

Antioxidative and acute anti-inflammatory effects of Campsis grandiflora flower

“…Although the synthesis of leukotrienes and prostaglandins has been reported to be involved in AA-and TPA-induced ear edema (Rao et al, 1993;Chen et al, 1994;Goulet et al, 1994), it has been reported that H 2 O 2 generation also play an important role in the edema formation in these models (Chung et al, 2001;Nakamura et al, 2003). As evidence in support of these findings, several antioxidative compounds have been reported to show anti-inflammatory action either on AA-induced ear edema (Crummey et al, 1987) or on TPA-induced ear edema (Hara et al, 1992;Sugiyama et al, 1994). The result that ECG, which showed antioxidative activity in vitro, and inhibited AA-induced ear edema (Fig.…”

Green synthesis and evaluation of the antitumor activity of a novel series of 3-[4-bi-(4-fluorophenyl)methylpiperazinyl]-4-amino-5-thione-1,2,4-triazole Schiff bases

“…Importantly, it has been recognized that fluorine-containing drugs are often far more therapeutically active than their non-fluorinated analogs, so the development of synthetic methods for fluorine-containing compounds and subsequent biochemical studies is an important field in organic fluorine chemistry and pharmaceutical chemistry [16,17]. 1-[Bi-(4-fluorophenyl)methyl]piperazine is an important intermediate in medicinal chemistry, and its derivatives have a wide variety of pharmacological properties, for example antitumor activity against CDC25B (cell division cycle 25 homolog B, from S. pombe) [18,19], calcium antagonism [20,21], anti-oxidation [22] and antihypertensive [23] activity. Unfortunately, very little is known about the pharmacological properties of 1,2,4-s-triazole Schiff bases containing the 1-[bi-(4-fluorophenyl)methyl]piperazine group.…”