19826-29-0

Upstream product

• 103-82-2 phenylacetic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 100-39-0 benzyl bromide 
• 100-51-6 benzyl alcohol 
• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 3892-92-0 (E)-3,4-dimethoxystilbene 

Downstream Products

• 40189-39-7 4-((E)-Styryl)-[1,2]benzoquinone 
• 112635-82-2 3-(3,4-diacetoxyphenyl)-2,3-dihydro-2-phenyl-6-(2-phenylvinyl)-1,4-benzodioxin 
• 1201129-58-9 C₂₈H₂₂O₄ 
• 112635-80-0 3-(3,4-hydroxyphenyl)-2,3-dihydro-2-phenyl-6-(2-phenylvinyl)-1,4-dioxin 

Relevant academic research and scientific papers

Developing glutathione-activated catechol-type diphenylpolyenes as small molecule-based and mitochondria-targeted prooxidative anticancer theranostic prodrugs

Developing concise theranostic prodrugs is highly desirable for personalized and precision cancer therapy. Herein we used the glutathione (GSH)-mediated conversion of 2,4-dinitrobenzenesulfonates to phenols to protect a catechol moiety and developed stable pro-catechol-type diphenylpolyenes as small molecule-based prooxidative anticancer theranostic prodrugs. These molecules were synthesized via a modular route allowing creation of various pro-catechol-type diphenylpolyenes. As a typical representative, PDHH demonstrated three unique advantages: (1) capable of exploiting increased levels of GSH in cancer cells to in situ release a catechol moiety followed by its in situ oxidation to o-quinone, leading to preferential redox imbalance (including generation of H2O2 and depletion of GSH) and final selective killing of cancer cells over normal cells, and is also superior to 5-fluorouracil and doxorubicin, the widely used chemotherapy drugs, in terms of its ability to kill preferentially human colon cancer SW620 cells (IC50 = 4.3 μM) over human normal liver L02 cells (IC50 = 42.3 μM) with a favourable in vitro selectivity index of 9.8; (2) permitting a turn-on fluorescent monitoring for its release, targeting mitochondria and therapeutic efficacy without the need of introducing additional fluorophores after its activation by GSH in cancer cells; (3) efficiently targeting mitochondria without the need of introducing additional mitochondria-directed groups.

THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS

The present invention relates to method(s) of treating a subject afflicted with a skin disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans- stilbene or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.

Radical-scavenging activity and mechanism of resveratrol-oriented analogues: Influence of the solvent, radical, and substitution

(Chemical Equation Presented). Resveratrol (3,5,4′-trihydroxy-trans- stilbene, 3,5,4′-THS) is a well-known natural antioxidant and cancer chemopreventive agent that has attracted much interest in the past decade. To find a more active antioxidant and investigate the antioxidative mechanism with resveratrol as the lead compound, we synthesized 3,5-dihydroxy-trans-stilbene (3,5-DHS), 4-hydroxy-trans-stilbene (4-HS) 3,4-dihydroxy-trans-stilbene (3,4-DHS), 4,4′-dihydroxy-trans-stilbene (4,4′-DHS), 4-hydroxy-3-methoxy-trans-stilbene (3-MeO-4-HS), 4-hydroxy-4′-methoxy- trans-stilbene (4′-MeO-4-HS), 4-hydroxy-4′-methyl-trans-stilbene (4′-Me-4-HS), 4-hydroxy-4′-nitro-trans-stilbene (4′-NO 2-4-HS), and 4-hydroxy-4′-trifluoromethyl-trans-stilbene (4′-CF3-4-HS). The radical-scavenging activity and detailed mechanism of resveratrol and its analogues (ArOHs) were investigated by the reaction kinetics with galvinoxyl (GO?) and 2,2-diphenyl-1- picrylhydrazyl (DPPH?) radicals in ethanol and ethyl acetate at 25°C, using UV-vis spectroscopy. It was found that the reaction rates increase with increasing the electron-rich environment in the molecules, and the compound bearing o-dihydroxyl groups (3,4-DHS) is the most reactive one among the examined resveratrol analogues. The effect of added acetic acid on the measured rate constant for GO?-scavenging reaction reveals that in ethanol that supports ionization solvent besides hydrogen atom transfer (HAT), the kinetics of the process is partially governed by sequential proton loss electron transfer (SPLET). In contrast to GO?, DPPH ? has a relatively high reduction potential and therefore enhances the proportion of SPLET in ethanol. The relatively low rate constants for the reactions of ArOHs with GO? or DPPH? in ethyl acetate compared with the rate constants in ethanol prove that in ethyl acetate these reactions occur primarily by the HAT mechanism. The contribution of SPLET and HAT mechanism depends on the ability of the solvent to ionize ArOH and the reduction potential of the free radical involved. Furthermore, the fate of the ArOH-derived radicals, i.e., the phenoxyl radicals, was investigated by the oxidative product analysis of ArOHs and GO? in ethanol. The major products were dihydrofuran dimers in the case of resveratrol, 4,4′-DHS, and 4-HS and a dioxane-like dimer in the case of 3,4-DHS. It is suggested from the oxidative products of these ArOHs that the hydroxyl group at the 4-position is much easier to subject to oxidation than other hydroxyl groups, and the dioxane-like dimer is formed via an o-quinone intermediate.

Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol

Resveratrol is a well-known natural antioxidant and cancer chemopreventive agent that has attracted much nterest in the past decade. Resveratrol-directed compounds were synthesized, and their antioxidant effects gainst reactive oxygen species (ROS)-induced DNA damage, their prooxidant effects on DNA damage in he presence cupric ions, and their cytotoxic and apoptosis-inducing effects on human promyelocytic leukemia(HL-60) cells were investigated in vitro. It was found that the compounds bearing o-diphenoxyl groups exhibited remarkably higher activities in inhibiting ROS-induced DNA damage, accelerating DNA damage in the presence cupric ions, and inducing apoptosis of HL-60 cells compared with the ones bearing no such groups. The detail mechanism of the structure-activity relationship was also studied by the oxidative product analysis of resveratrol and its analogues with galvinoxyl radical or cupric ions and UV-visible spectra change in the presence cupric ions. This study reveals a good and interesting correlation between antioxidant and prooxidant activity, as well as cytotoxicity and apoptosis-inducing activity against HL-60 cells, and provides an idea for designing antioxidant-based cancer chemoprevention agents. ?2009 American Chemical Society.

Titanium phthalocyanines with axial phenylenevinylenes

The synthesis of soluble titanium(IV) phthalocyanines, axially substituted with phenylenevinylenes (PVs) (RxPcTiX), is described. The reaction of peripherally tetra- and octasubstituted (phthalocyaninato)titanium oxides (RxPcTiO) 1-3

Substituted CIS- and trans-stilbenes as therapeutic agents

The present invention relates to method(s) of treating a subject afflicted with cancer or a precancerous condition, an inflammatory disease or condition, and/or stroke or other ischemic disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans-stilbene.

Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor alpha-induced activation of transcription factor nuclear factor kappaB

The transcription factor nuclear factor kappaB (NF-κB), which regulates expression of numerous antiinflammatory genes as well as genes that promote development of the prosurvival, antiapoptotic state is up-regulated in many cancer cells. The natural product resveratrol, a polyphenolic trans-stilbene, has numerous biological activities and is a known inhibitor of activation of NF-κB, which may account for some of its biological activities. Resveratrol exhibits activity against a wide variety of cancer cells and has demonstrated activity as a cancer chemopreventive against all stages, i.e., initiation, promotion, and progression. The biological activities of resveratrol are often ascribed to its antioxidant activity. Both antioxidant activity and biological activities of analogues of resveratrol depend upon the number and location of the hydroxy groups. In the present study, phenolic analogues of resveratrol and a series of substituted trans-stilbenes without hydroxy groups were compared with resveratrol for their abilities to inhibit the human tumor necrosis factor alpha-induced (TNF-α) activation of NF-κB, using the Panomics NF-κB stable reporter cell line 293/NF-κB-luc. A series of 75 compounds was screened to identify substituted trans-stilbenes that were more active than resveratrol. Dose-response studies of the most active compounds were carried out to obtain IC50 values. Numerous compounds were identified that were more active than resveratrol, including compounds that were devoid of hydroxy groups and were 100-fold more potent than resveratrol. The substituted trans-stilbenes that were potent inhibitors of the activation of NFκB generally did not exhibit antioxidant activity. The results from screening were confirmed using BV-2 microglial cells where resveratrol and analogues were shown to inhibit LPS-induced COX-2 expression.

Hydroxystilbene compounds for reducing/inhibiting protein glycation

The hydroxystilbenes are well suited for reducing or inhibiting the glycation of certain substrates, for example the proteins of nails and/or hair, advantageously to preventatively and/or curatively combat glycation-related aging of the nails/hair.

Efficiency and structure-activity relationship of the antioxidant action of resveratrol and its analogs

Resveratrol and its analogs, six other polyhydroxystilbenes, were synthesized and their antioxidative activities were evaluated in vitro by determination of the levels of malondialdehyde and hydrogen peroxide. Results clearly exhibited that resveratrol and its analogs had various potencies in inhibiting lipid peroxidation in rat brain, kidney, and liver homogenates and rat erythrocyte hemolysis. Several polyhydroxystilbenes were found to be more active than resveratrol in these models, and structure-activity relationship studies on polyhydroxystilbenes are described in this paper.

Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol

A series of hydroxylated trans-stilbene related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxy stilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function.A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product.Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly.The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.