DPPH radical scavenging activity of paracetamol analogues

被引：19

作者：

Alisi, Maria Alessandra ^{[2
]}

Brufani, Mario ^{[3
]}

Cazzolla, Nicola ^{[2
]}

Ceccacci, Francesca ^{[1
]}

Dragone, Patrizia ^{[2
]}

Felici, Marco ^{[1
]}

Furlotti, Guido ^{[2
]}

Garofalo, Barbara ^{[2
]}

La Bella, Angela ^{[1
]}

Lanzalunga, Osvaldo ^{[1
]}

Leonelli, Francesca ^{[1
]}

Bettolo, Rinaldo Marini ^{[1
]}

Maugeri, Caterina ^{[2
]}

Migneco, Luisa Maria ^{[1
]}

Russo, Vincenzo ^{[2
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[2] ACRAF SpA, Angelini Res Ctr, Dipartimento Chim, I-00040 Rome, Italy

[3] Univ Roma La Sapienza, Dipartimento Sci Biochim, I-00185 Rome, Italy

来源：

TETRAHEDRON | 2012年 / 68卷 / 49期

关键词：

DPPH; Radical scavenging; Antioxidant; Paracetamol; Analogues; LOSS ELECTRON-TRANSFER; HYDROGEN-ATOM ABSTRACTION; ANTIOXIDANT ACTIVITY; 3,5-DISUBSTITUTED ANALOGS; PHENOLIC ANTIOXIDANTS; LIPID-PEROXIDATION; ACID-DERIVATIVES; VITAMIN-E; ACETAMINOPHEN; 2,2-DIPHENYL-1-PICRYLHYDRAZYL;

D O I：

10.1016/j.tet.2012.09.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Biochemical studies suggest a direct relationship between the radical scavenging activity of paracetamol (I) and its antipyretic and analgesic action. To evaluate the effect of chemical modifications on the radical scavenging activity of compounds of type I, analogues 1-14 were prepared and submitted to a stable free radical (DPPH; 1,1-diphenyl-2-picryl-hydrazyl) assay. All paracetamol derivatives showed a significant higher efficiency than the parent compound. This study showed that radical scavenging activity can be increased by decreasing the phenolic ortho substituents steric hindrance or by introducing substituents on the acyl moiety like an indazole ring or the ionic N-methyl morpholinium group. A significant activating effect was also observed by replacing the 1,4-acylamidophenol with a 1,4-acylamidonaphthol system. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：10180 / 10187

页数：8

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