A DFT study for paracetamol and 3,5-disubstituted analogues

被引：51

作者：

Diniz, JEM ^{[1
]}

Borges, RS ^{[1
]}

Alves, CN ^{[1
]}

机构：

[1] UFPA, Ctr Ciencias Exatas & Nat, Dept Quim, BR-66075110 Belem, PA, Brazil

来源：

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM | 2004年 / 673卷 / 1-3期

关键词：

paracetamol analogues; analgesic activity; cytotoxicity; DFT; spin density;

D O I：

10.1016/j.theochem.2003.12.002

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Quantum chemistry calculations at the B3LYP theory level, together with the 6-31G* basis set were employed to obtain energy (E), ionization potential (IP), bond dissociation energies (BDE), and spin-density distribution for paracetamol (PAR) and 3,5-disubstituted analogues of PAR. Calculations of spin densities were performed for radical formed by hydrogen abstraction from the phenolic hydroxyl group. The unpaired electron remains is localized on the O-7 phenolic oxygen (31-40%), C-3 and C-5 carbon atoms at the ortho (17-27 and 21-27%) and C-1 carbon atom at the para (25-33%) positions. The correlation between analgesic activity, cytotoxicity, and electronic properties was obtained by using correlation matrix. The IP, and BDEO-H are significant related with the in vitro inhibition of cyclooxygenase, while BDEO - H, BDEN - H and IP are significant related with the cytotoxicity (LDH). (C) 2004 Elsevier B.V. All rights reserved.

引用

页码：93 / 97

页数：5