The obtained results indicated that the early vascular permeability measured at 30 min of zymosan-induced peritonitis was significantly inhibited in groups receiving BMTBA (10, 30, 50 mg/kg). The early infiltration of neutrophils measured at 4 hours of zymosan-induced peritonitis was inhibited in the group receiving BMTBA (50 mg/kg) and tetranor-DHLA (50 mg/kg). The results indicated that the increase in paw edema was significantly inhibited in the groups receiving BMTBA (50, 100 mg/kg) and tetranor-DHLA (30, 50 mg/kg). In summary, the present studies clearly demonstrated that both BMTBA and tetranor-DHLA were able to act as anti-inflammatory agents. This is the first study examining in vivo the anti-inflammatory properties of LA metabolites.
A comparison of hydrogen bond strengths in various enamines was made by monitoring the differential shifts Dd(X) as the difference of NMR chemical shifts between E and Z forms of the nuclei directly involved in hydrogen bonding, i.e., X = 15 N, 1 H, 17 O atoms. The interpretation of these differential values was aided by ab initio calculations and X-ray derived geometric parameters for selected compounds. It is shown that Dd(N 1 H) and Dd( 15 N) give conclusive results and their changes are rationally interpreted by invoking established contributing effects that influence the values of chemical shifts. The Dd( 17 O) parameter is sensitive to intramolecular geometry, mainly bond angles around oxygen and co-planarity of the atoms forming the hydrogen bonds. The latter factor is important in determining the strength of hydrogen bonds. Even a weak acceptor such as the lactone function gives a relatively strong hydrogen bond as compared with sp 3 -hybridized sulfonyl or sulfinyl acceptors. The hybridization of the penultimate atom of an acceptor plays a crucial role in determining the strength of hydrogen bonding. P A P E R NJC www.rsc.org/njc 1562 N e w J . C h e m . , 2 0 0 4 , 2 8 , 1 5 6 2 -1 5 6 7
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