1236211-45-2Relevant academic research and scientific papers
Understanding the regioselectivity in the oxidative condensation of catechins using pyrogallol-type model compounds
Yanase, Emiko,Ochiai, Yuto,Hirose, Sayumi
, p. 12359 - 12366 (2020/11/10)
Catechins are found in many foods, including tea. These compounds are bioactive. Previous studies have shown that catechins form dimers on oxidation, and there seem to be distinct regioselective effects. However, the dimerization mechanism and regioselectivity are not well understood. Therefore, we investigated the oxidation of four pyrogallol-type model compounds of epigallocatechin (EGC) having various substituents with 1 equiv of copper chloride and 30% dioxane in water. Compounds having 2C-2C or 2C-4C bonds in the B-ring were obtained in different product ratios. Comparison of the oxidation rates of each compound revealed that the model compounds having an oxygen atom corresponding to the 1-position of the C-ring of EGC underwent slow oxidation. In addition, using density functional theory calculations, we found that the highest occupied molecular orbital energies of these compounds were higher than those of the others. Further, the 2C-2C-bonded oxidation product having an A-ring and an oxygen atom at the C-ring 1-position was confirmed to have the highest thermodynamic stability. From these results, it is suggested that the regioselective condensation reaction of the catechin B-ring is related to interactions between the A-rings, as indicated by earlier studies, and the presence of oxygen at the 1-position of the C-ring in EGC.
Inhibitors of protein activity for the treatment of angiogenesis and SOX18/or lymphangiogenesis-related diseases
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Paragraph 0152; 0160; 0165; 0262, (2020/01/04)
Disclosed are compounds of a formula provided herein that show efficacy in the inhibition of SOX18 protein activity, and in particular with respect to the ability of SOX18 to bind DNA and/or particular protein partners. Further, methods of treating angiog
Efficient synthesis of anacardic acid analogues and their antibacterial activities
Mamidyala, Sreeman K.,Ramu, Soumya,Huang, Johnny X.,Robertson, Avril A.B.,Cooper, Matthew A.
, p. 1667 - 1670 (2013/04/10)
Anacardic acid derivatives exhibit a broad range of biological activities. In this report, an efficient method for the synthesis of anacardic acid derivatives was explored, and a small set of salicylic acid variants synthesised retaining a constant hydrophobic element (a naphthyl tail). The naphthyl side chain was introduced via Wittig reaction and the aldehyde installed using directed ortho-metalation reaction of the substituted o-anisic acids. The failure of ortho-metalation using unprotected carboxylic acid group compelled us to use directed ortho-metalation in which a tertiary amide was used as a strong ortho-directing group. In the initial route, tertiary amide cleavage during final step was challenging, but cleaving the tertiary amide before Wittig reaction was beneficial. The Wittig reaction with protected carboxylic group (methyl ester) resulted in side-products whereas using sodium salt resulted in higher yields. The novel compounds were screened for antibacterial activity and cytotoxicity. Although substitution on the salicylic head group enhanced antibacterial activities they also enhanced cytotoxicity.
MOLECULARLY IMPRINTED POLYMERS
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, (2012/03/12)
The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
