72375-01-0Relevant articles and documents
Structure-activity relationship study on col-003, a protein-protein interaction inhibitor between collagen and Hsp47
Yoshida, Masahito,Saito, Masazumi,Ito, Shinya,Ogawa, Koji,Goshima, Naoki,Nagata, Kazuhiro,Doi, Takayuki
, p. 220 - 226 (2020/11/26)
This study demonstrates the structure-activity relationship of Col-003, a potent collagen-heat-shock protein 47 (Hsp47) interaction inhibitor. Col-003 analogues were successfully synthesized by Pd(0)-catalyzed cross-coupling reactions of 5-bromosalicylald
Characterization of scavengers of γ-ketoaldehydes that do not inhibit prostaglandin biosynthesis
Zagol-Ikapitte, Irene,Amarnath, Venkataraman,Bala, Manju,Roberts II, L. Jackson,Oates, John A.,Boutaud, Olivier
scheme or table, p. 240 - 250 (2011/02/22)
Expression of cyclooxygenase-2 (COX-2) is associated with the development of many pathologic conditions. The product of COX-2, prostaglandin H2 (PGH2), can spontaneously rearrange to form reactive γ-ketoaldehydes called levuglandins (LGs). This γ-ketoaldehyde structure confers a high degree of reactivity on the LGs, which rapidly form covalent adducts with primary amines of protein residues. Formation of LG adducts of proteins has been demonstrated in pathologic conditions (e.g., increased levels in the hippocampus in Alzheimer's disease) and during physiologic function (platelet activation). On the basis of knowledge that lipid modification of proteins is known to cause their translocation and to alter their function, we hypothesize that modification of proteins by LG could have functional consequences. Testing this hypothesis requires an experimental approach that discriminates between the effects of protein modification by LG and the effects of cyclooxygenase-derived prostanoids acting through their G-protein coupled receptors. To achieve this goal, we have synthesized and evaluated a series of scavengers that react with LG with a potency more than 2 orders of magnitude greater than that with the ε-amine of lysine. A subset of these scavengers are shown to block the formation of LG adducts of proteins in cells without inhibiting the catalytic activity of the cyclooxygenases. Ten of these selective scavengers did not produce cytotoxicity. These results demonstrate that small molecules can scavenge LGs in cells without interfering with the formation of prostaglandins. They also provide a working hypothesis for the development of pharmacologic agents that could be used in experimental animals in vivo to assess the pathophysiological contribution of levuglandins in diseases associated with cyclooxygenase up-regulation.
Acidic rearrangement of (benzyloxy)chalcones: A short synthesis of chamanetin
Sagrera, Gabriel,Seoane, Gustavo
scheme or table, p. 4190 - 4202 (2011/03/20)
Treatment of (benzyloxy)chalcones with trifluoroacetic acid in refluxing chloroform gave several new benzyl(hydroxy)flavanones in high yields and good regioselectivities. By using this procedure, we prepared the natural compound chamanetin in good yield from readily available reagents. Georg Thieme Verlag Stuttgart - New York.
Solid-supported acids for debenzylation of aryl benzyl ethers
Petchmanee, Thaninee,Ploypradith, Poonsakdi,Ruchirawat, Somsak
, p. 2892 - 2895 (2007/10/03)
Solid-supported acids have been investigated for aromatic debenzylation reactions. Stoichiometric amounts of solid-supported acids in refluxing toluene with or without 4 equiv of methanol effectively provided the desired aromatic debenzylation products of various systems in moderate to excellent yields (up to 98%).
