Premium
On the Importance of CH/π and CH⋅⋅⋅HC Interactions in the Solid State Structure of 15‐Lipoxygenase Inhibitors Based on Eugenol Derivatives
Author(s) -
Mirzaei Masoud,
Nikpour Mohsen,
Bauzá Antonio,
Frontera Antonio
Publication year - 2015
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201500287
Subject(s) - chemistry , eugenol , lipoxygenase , solid state , stereochemistry , organic chemistry , enzyme
In this manuscript the X‐ray structures of two potent and known inhibitors of 15‐lipoxygenase, that is, 4‐allyl‐2‐methoxyphenyl‐1‐admantanecarboxylate ( 1 ) and allyl‐2‐methoxyphenyl‐1‐cyclohexanecarboxylate ( 2 ), are reported. Their solid‐state architectures show that they have a strong ability to establish CH/π and CH⋅⋅⋅HC interactions. For the former interaction, the adamantane or cyclohexane moieties are the CH donors and the electron‐rich methoxyphenyl ring is the π system. For the latter, the CH bonds belong to the aliphatic rings of the inhibitors. Interestingly, the active site of lipoxygenase enzyme family is rich in isoleucine and leucine amino acids that participate in the binding of the unsaturated fatty acid substrate by means of multiple hydrophobic CH⋅⋅⋅HC interactions. By means of theoretical calculations, we analyze the ability of compounds 1 and 2 to establish CH/π and CH⋅⋅⋅HC interactions in the solid state.