Gene/Protein Disease Symptom Drug Enzyme Compound
Pivot Concepts:   Target Concepts:
Query: KEGG:D02003 (NBT)
 1,323 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The combination of 5-LOX inhibition and retinoid activity in one molecule could be an interesting pharmacological tool to influence psoriasis. Thus we synthesized compounds with arotinoid structure by anellation of the 5-LOX inhibitors 1 and 2 with 1,1,4,4-tetramethylcyclohexane. A key step was the CuCl-MeCN-O2 oxidation of tetrahydroanthracenol 13 to the corresponding 1,2-anthraquinone 14 which could be converted to the analogous 2-hydroxy-1,4-anthraquinone 19 by Thiele-Winter reaction followed by oxidation. The halogenated quinones 9 and 21 were arylated with 2,6-di-tertbutylphenol and demethylated or hydrolyzed to the target compounds 3 and 4 which were tested in comparison with the non-anellated 5-LOX inhibitors 1 and 2 for LOX inhibition in activated human granulocytes and for antioxidative activity by the method of Popov with the chemiluminometer Photochem. The results are discussed in relation to the corresponding logP values. The 1,2-quinones 1 and 3 are more potent 5-LOX inhibitors than their 1,4-analogues 2 and 4, the tetrahydroanthraquinon derivatives 3 and 4 are less potent than the naphthoquinones 1 and 2. All compounds are devoid of any activity in cell differentiation as compared to retinoic acid as indicated by the NBT test with HL-60 leukemia cells.
 ...
PMID:[Partially hydrogenated aryl-1,2/1,4-anthraquinone derivatives, 5-lipoxygenase inhibitors with arotinoid structure]. 1148 69

Six new iridoid glucosides, 6'-O-trans-feruloylnegundoside (1), 6'-O-trans-caffeoylnegundoside (2), 2'-O-p-hydroxybenzoyl-6'-O-trans-caffeoylgardoside (3), 2'-O-p-hydroxybenzoyl-6'-O-trans-caffeoyl-8-epiloganic acid (4), 2'-O-p-hydroxybenzoyl gardoside (5), and 2'-O-p-hydroxybenzoyl-8-epiloganic acid (6), along with two known iridoids, agnuside and negundoside, have been isolated from the ethyl acetate extractive of the leaves of Vitex altissima. The structures of these compounds were elucidated on the basis of spectral data interpretation. These isolates did not exhibit significant 5-lipoxygenase enzyme inhibitory activity, but compounds 2-4 showed potent antioxidant activity by both the superoxide (NBT riboflavin photoreduction) free-radical-scavenging and DPPH-radical-scavenging methods. Compounds 1, 2, and negundoside were evaluated in a rat paw edema assay.
 ...
PMID:New acylated iridoid glucosides from Vitex altissima. 1562 Feb 43

A series of four naturally occurring homoisoflavonoids and eight analogs have been synthesized starting from an appropriately substituted phenol through chroman-4-one, in four steps. The products were assigned as E-isomers based on NMR spectroscopic data. The E-isomers were converted into Z-isomers by photoisomerization. The E- and Z-isomers showed distinct chemical shifts and the differences between (E) and (Z)-homoisoflavonoids in the proton NMR spectra afford a useful method for ascertaining the stereochemistry. The antioxidant activity of homoisoflavonoids was determined by superoxide (NBT) and DPPH free radical scavenging methods. The analog 7-hydroxy-3-[(3,4,5-trihydroxyphenyl)methylene]chroman-4-one displayed excellent activity followed by sappanone A in both the methods and were several times potent than the commercial antioxidants like BHA, BHT, etc. These compounds were evaluated in vitro for their inhibitory activities against 5-lipoxygenase (5-LOX) enzyme. The analog 7-hydroxy-3-[(N,N-dimethylaminophenyl)methylene]chroman-4-one was found to possess potent inhibitory activity and was comparable to that of the standard, nordihydroguiaretic acid. These results suggest that these homoisoflavonoids, with their potent antioxidant and 5-LOX inhibitory activities, may have useful applications as antioxidants and lead compounds for asthma and inflammatory diseases.
 ...
PMID:Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids. 1633 86