95063-02-8Relevant articles and documents
Chemo-enzymatic synthesis of vinyl and L-ascorbyl phenolates and their inhibitory effects on advanced glycation end products
Hwang, Seung Hwan,Wang, Zhiqiang,Lim, Soon Sung
, p. 726 - 735 (2016/08/04)
This study successfully established the feasibility of a two-step chemo-enzymatic synthesis of L-ascorbyl phenolates. Intermediate vinyl phenolates were first chemically produced and then underwent trans-esterification with L-ascorbic acid in the presence of Novozyme 435 (Candida Antarctica lipase B) as a catalyst. Twenty vinyl phenolates and 11 ascorbyl phenolates were subjected to in vitro bioassays to investigate their inhibitory activity against advanced glycation end products (AGEs). Among them, vinyl 4-hydroxycinnamate (17VP), vinyl 4-hydroxy-3-methoxycinnamate (18VP), vinyl 4-hydroxy-3,5-dimethoxycinnamate (20VP), ascorbyl 4-hydroxy-3-methoxycinnamate (18AP) and ascorbyl 3,4-dimethoxycinnamate (19AP) showed 2–10 times stronger inhibitory activities than positive control (aminoguanidine and its precursors). These results indicated that chemo-enzymatically synthesized compounds have AGE inhibitory effect and thus are effective in either preventing or retarding glycation protein formation.
Substituent Effects on the Intramolecular Photochemical Reactions of Phenyl-Ethenyl Non-conjugated Bichromophoric Systems
Ellis-Davies, Graham C. R.,Gilbert, Andrew,Heath, Peter,Lane, Jon C.,Warrington, John V.,Westover, David L.
, p. 1833 - 1842 (2007/10/02)
The effects of substitution on the photochemistry of phenyl-ethenyl bichromophoric systems are reported.Methyl substitution at the 2-, 3-, 5-, and 1,1,2-positions in the pentene moiety of 5-phenylpent-1-ene reduces both reaction efficiency and selectivity but in contrast to intramolecular analogues the photoreaction of 3-phenethylcyclohexene is comparable with that of the corresponding cyclopentene.Incorporation of ester units in the connecting unit between the chromophores or on the ethene inhibits intramolecular cyclisation as does the presence of para OMe, CN, or COMe groups in 5-phenylpent-1-ene.In contrast reaction selectivity and efficiency are greatly promoted by ortho Me or OMe groups and the products reflect exlusive 1,3-cycloaddition.The presence of a para Me group in 5-phenylpent-1-ene leads to specific 2,6-intramolecular cyclisation but the reaction of the meta-Me derivative leads to four products derived from 1,3- and 1,5-intramolecular cycloaddition.The observations are discussed in terms of mechanisms of arene-ethene photoreactions and preferred conformations of the bichromophores.
