Synthesis and biological evaluation of a novel series of bis-salicylaldehydes as mushroom tyrosinase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 20, 2010, Pages 6138-6140

  Delogu, Giovanna ^a   Podda, Gianni ^a   Corda, Marcella ^a   Fadda, Maria Benedetta ^a   Fais, Antonella ^a   Era, Benedetta ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Bis salicylaldehydes; Mushroom tyrosinase; Non competitive inhibitor; Tyrosinase inhibitor

Indexed keywords

3,3' DIHYDROXY 5,5' METHYLENE BIS SALICYLALDEHYDE; 3,3' DIMETHOXY 5,5' METHYLENE BIS SALICYLALDEHYDE; 4,4' DIHYDROXY 5,5' METHYLENE BIS SALICYLALDEHYDE; 4,4' DIMETHOXY 5,5' METHYLENE BIS SALICYLALDEHYDE; BENZALDEHYDE DERIVATIVE; KOJIC ACID; LEVODOPA; SALICYLALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; NONHUMAN; OXIDATION;

AGARICALES; ALDEHYDES; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION;

BASIDIOMYCOTA;

EID: 77956907512     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.018     Document Type: Article

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17. 3) δ (ppm): 39.35, 117.92, 120.41, 131.90, 133.15, 137.52, 160.14, 196.34. MS m/z (%): 256 (100), 227 (67), 209 (17), 199 (25), 181 (75), 152 (12), 135 (22), 107 (15), 77 (22).
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19. 3) δ (ppm): 40.44, 56.37, 113.32, 123.84, 127,58, 133.02, 150, 40, 196.38. MS m/z (%): 316 (100), 288 (12), 270 (5), 165 (8).
20. 6: C, 64.55; H, 5.10. Found: C, 64.7; H, 5.22.
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23. 3,3′-Dihydroxy-5,5′-methylene-bis-salicylaldehyde (5). It was obtained with a yield of 51%: mp: 190-192 °C (Ref.21 188-189 °C, yield 41%).
24. 6: C, 62.50; H, 4.20. Found: C, 62.54; H, 4.22.
25. 50 value, a concentration giving 50% inhibition of tyrosinase activity, was determined by interpolation of dose-response curves. The activity of mushroom tyrosinase was determinate by spectrophotometric techniques (Varian Cary 50). Kojic acid was used as a reference tyrosinase inhibitor.