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Design and Synthesis of 4-methoxyphenylacetic Acid Esters as 15-lipoxygenase Inhibitors and SAR Comparative Studies of Them

Design and Synthesis of 4-methoxyphenylacetic Acid Esters as 15-lipoxygenase Inhibitors and SAR Comparative Studies of Them

Hamid Sadeghian, Neda Attaran, Zeinab Jafari, Mohammad Reza Saberi, Seyed Mohammad Seyedi, Hossein Eshghi, Mehdi Pordel, Mohammad Mahdi Riazi

Bioorg Med Chem. 2009 Mar 15;17(6):2327-35.

PMID: 19251422

Abstract:

A group of 4-methoxyphenylacetic acid esters were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compounds 7d-e showed the best IC(50) in SLO inhibition (IC(50)=3.8 and 1.9 microM, respectively). All compounds were docked in SLO active site and showed that carbonyl group of compounds is oriented toward the Fe(III)-OH moiety in the active site of enzyme and fixed by hydrogen bonding with hydroxyl group. It is assumed that lipophilic interaction of ligand-enzyme would be in charge of inhibiting the enzyme activity. The selectivity of the synthetic esters in inhibiting of 15-HLOb was also compared with 15-HLOa by molecular modeling and multiple alignment techniques.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP104018	4-Methoxyphenylacetic acid		104-01-8	Price

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