Diastereoisomers of 2-benzyl-2, 3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol: Potential anti-inflammatory agents

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 20, 2009, Pages 5927-5930

  Sheridan, Helen ^a   Walsh, John J ^a   Cogan, Carina ^a   Jordan, Michael ^a   McCabe, Tom ^a   Passante, Egle ^a   Frankish, Neil H ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Anti inflammatory; Indane; Indane dimers; Mast cells; RBL 2H3 cells

Indexed keywords

1 INDANONE; 2 BENZYL 2, 3 DIHYDRO 2 (1H INDEN 2 YL) 1H INDEN 1 OL; 2 INDANONE; ALCOHOL; ANTIINFLAMMATORY AGENT; ARACHIDONIC ACID; ETHER DERIVATIVE; INDANONE DERIVATIVE; INDOMETACIN; KETONE; NIFEDIPINE; SILYL ETHER; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG ACTIVITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; RAT; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BETA-N-ACETYLHEXOSAMINIDASES; CELL LINE; CRYSTALLOGRAPHY, X-RAY; GUINEA PIGS; HISTAMINE; INDENES; MICE; MOLECULAR CONFORMATION; RATS; STEREOISOMERISM;

EID: 70349462696     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.08.060     Document Type: Article

References (22)

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12. Sheridan, H.; Walsh, J. J; Jordan, M.; Cogan, C.; Frankish, N. Eur. J. Med Chem., submitted for publication.
13. 2) [AB system], 5.02 (1H, m, CHOH), 6.64 (1H, s, CH{double bond, long}C), 6.91-6.94 (2H, m, ArH), 7.10-7.31 (9H, br m, ArH), 7.35-7.40 (2H, m, ArH).
14. Sheridan, H.; Walsh, J. J.; McCabe, T.; Passante, E.; Cogan, C.; Jordan, M.; Frankish, N., X-ray crystal data deposit. CCDC deposition number: 733630, 2009.
15. Passante E., Carsten E., Sheridan H., and Frankish N. Inflamm. Res. 58 (2009) 611
16. 6
17. 9
18. 2 in 24-well plates for experiments.
19. 2 and 37 °C. The β-hexosaminidase activity was assayed according to a previously published method, [2]. Briefly, 30 μL of supernatant were transferred into a 96-well plate. Fifty microliters of substrate solution were added (1.3 mg/mL of p-nitrophenyl N-acetyl-d-glucosaminide (Sigma) in citrate buffer, pH 4.5) and the plate was incubated for 1 h at 37 °C. The reaction was stopped by adding 80 μL of NaOH (0.5 M) to each well and the formed p-nitrophenolate was measured spectrophotometrically in a 96-well plate reader (FLUOstar OPTIMA, BMG Labtech, Aylesbury, UK) at a wavelength of 405 nm. The absorption was converted into the percentage of total cellular β-hexosaminidase activity by comparison with the absorption produced by a Triton X-100 (Sigma) lysate of the same cells according to the following equation:% total enzyme activity = [(secreted - spontaneous)/total content] * 100. Incubations were performed in triplicate. The percentage of the vehicle was always maintained at 0.5% of the volume of the supernatant.
20. Passante E., Carsten E., Sheridan H., and Frankish N. FASEB J. 21 (2007) A442
21. Mouse ear oedema: The mouse ear oedema model was performed using Balb/C mice (25-35 g), of either sex. The left ear was treated by the topical application (10 μL) of solvent (acetone 100%). To the right ear was applied 10 μL test compound (300 μg/ear in acetone), indomethacin (300 μg/ear in acetone) or dexamethasone (100 μg/ear in acetone). After 1 h, oedema was induced by the topical application of arachidonic acid (10 μL of 400 mg/mL in acetone). The width of each ear was measured, both before and 60 min after the induction of oedema, using a micrometer screw gauge. Ear oedema was calculated by comparing the left and right ear width after induction of oedema and expressed as percentage normal. Values are expressed as a mean ± SEM and statistical comparisons between groups was performed by one way Anova, followed by Dunnet's Multiple Comparison test as a post-test. Data were displayed and statistical analysis was performed using Prism 4 software. Animals were sacrificed according to guidelines laid down by the working party report (Laboratory Animals (1996) 30, 293-316, Laboratory Animals (1997) 31, 1-32), on Directive 86/609/EEC (No. L 358, ISSN 0378-6978), which is endorsed by the Bioresources Ethical Review Committee of the University.
22. Passante E., Ehrhardt C., Sheridan H., and Frankish N. Inflamm. Res. 57 (2008) 15