268232-54-8

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 33617-42-4 (3,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 

Downstream Products

• 1446272-88-3 (E)-2,2'-(5-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)styryl)-1,3-phenylene)bis(oxy)bis(tetrahydro-2H-pyran) 
• 1370024-27-3 (E)-(5-(4-hydroxymethyl)styryl)benzene-1,3-diol 
• 400608-32-4 5-[(4-hydroxyphenyl)ethynyl]-1,3-benzenediol 
• 1582271-17-7 3,5-bis(tetrahydro-2H-pyran-2-yloxy)ethynylbenzene 

Relevant academic research and scientific papers

Anti-diabetic activity of fused PPARγ-SIRT1 ligands with limited body-weight gain by mimicking calorie restriction and decreasing SGK1 expression

A series of benzothiazol-2-one containing α-ethoxyphenylpropionic acid derivatives incorporating resveratrol or butein scaffolds were designed as fused full PPARγ agonist ligands and SIRT1-activating compounds for the treatment of type 2 diabetes (T2D) an

Novel analogues of resveratrol: Metabolism and inhibition of colon cancer cell proliferation

Resveratrol is a phytochemical present in the skin of red grapes, and hence red wine as well as a variety of berries and nuts. It is an anti-oxidant, which has shown cancer chemopreventive properties in preclinical rodent models of carcinogenesis. The bioavailability of resveratrol is low, as it is rapidly metabolised to glucuronides and sulfates. The pharmacological activities of conjugate metabolites of phenols are often much lower than those of their metabolic progenitors. Therefore chemical synthetic manipulations aimed at slowing the rate of metabolic conjugation of phenols may generate analogues with increased bioavailability and efficacy. Here we describe the synthesis using the Wittig-Horner-Emmons reaction of a new series of resveratrol analogues in which the phenol moieties were systematically replaced by hydroxymethyl and/or methoxy groups. Incubation of analogues, which lack phenol groups with phase II metabolising enzyme preparations generated hardly any, or only small amounts of, conjugates. Four of the new analogue inhibited the growth of human-derived HCA-7 colon cancer cells, but with much less potency than resveratrol.

Effects of polyphenol compounds on influenza A virus replication and definition of their mechanism of action

A set of polyphenol compounds was synthesized and assayed for their ability in inhibiting influenza A virus replication. A sub-set of them showed low toxicity. The best compounds within this sub-set were 4 and 6g, which inhibited the viral replication in a dose-dependent manner. The antiviral activity of these molecules was demonstrated to be caused by their interference with intracellular pathways exploited for viral replication: (1) MAP kinases controlling nuclear-cytoplasmic traffic of viral ribonucleoprotein complex; (2) redox-sensitive pathways, involved in maturation of viral hemagglutinin protein.

Vitamin D analogues

The invention concerns novel bi-aromatic compounds having the formula: which are analogs of vitamin D, the process of preparing them, as well as their use in pharmaceutical compositions in human or veterinary medicine, particularly in dermatology, cancer treatment, treatment of auto-immune diseases, and in organ or tissue transplants. Cosmetic compositions and methods of use are also included.

Synthesis and aromatase inhibitory activity of flavanones

Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors; therefore, in an effort to develop novel anti breast cancer agents, B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern. Methods. A series of flavanones was prepared by cyclisation of 2′hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity of these compounds was investigated using human placental microsomes and radiolabeled [1,2,6,7-3H]-androstenedione as substrate. Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring substitution pattern. Hydroxylation at position 3′ and/or 4′ enhanced the anti-aromatase activity; thus, 3′,4′-dihydroxy-7-methoxyflavanone was found to be twice more potent than aminoglutethimide, the first aromatase inhibitor clinically used. Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.