2284-30-2Relevant articles and documents
-
Salkind,Kachniaschwili
, (1950)
-
Candida antarctica lipase B-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxy groups
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei
, p. 44 - 49 (2016/01/16)
Candida antarctica lipase B proved to be highly active in the deacylation of substituted hydroquinones and resorcinols acylated at both phenolic hydroxy groups. The deacylation reactions were much faster than the corresponding direct acylations of these dihydroxybenzenes catalyzed by the same lipase. More importantly, they took place generally in a markedly regioselective manner: the acyloxy group remote from the substituent was preferentially cleaved. The main or exclusive products obtained were the regioisomers of those produced through the direct acylation of the dihydroxybenzenes. In the case of alkyl-substituted hydroquinone derivatives, the regioselectivity increased with an increase in the bulk of the substituent. In the case of 4-substituted diacylated resorcinols, the 3-O-monoacyl derivatives were obtained generally as the sole products. Quite interestingly, some secondary alcohols proved to act as better acyl acceptors than the corresponding primary alcohols in these enzymatic deacylations.
Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues
Petronzi, Carmen,Filosa, Rosanna,Peduto, Antonella,Monti, Maria Chiara,Margarucci, Luigi,Massa, Antonio,Ercolino, Simona Francesca,Bizzarro, Valentina,Parente, Luca,Riccio, Raffaele,De Caprariis, Paolo
, p. 488 - 496 (2011/03/19)
As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophage-like RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E2 (PGE2). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for hsPLA2, surface plasmon resonance (SPR) experiments were performed.
