67901-95-5

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 42766-36-9 potassium p-methoxyphenylacetate 

Downstream Products

• 56177-99-2 (E)-3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)-acrylic acid methyl ester 
• 73867-57-9 6,7-dimethoxy-3-(4'-methoxyphenyl)coumarin 
• 73867-60-4 1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acetylene 
• 73867-59-1 2-acetoxy-1-(4-methoxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone 
• 73867-58-0 (Z)-α-acetoxy-3',4,4'-trimethoxystilbene 
• 18513-95-6 (E)-3,4,4'-trimethoxystilbene 
• 106053-26-3 (Z)-1-(4-methoxyphenyl)-2-(3,4-dimethoxyphenyl)ethene 
• 94773-80-5 3-(3,4-dimethoxy-phenyl)-2-(4-methoxy-phenyl)-propionic acid 

Relevant academic research and scientific papers

The first synthesis of phenylpropanoid derivative bromophenols including natural products: Formation of an indene derivative compound

Synthesis of the natural bromophenols 3,4-dibromo-5-(butoxymethyl)benzene-1,2-diol, (E)-3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-methylacrylaldehyde (7), 3,4-dibromo-5-(3-hydroxy-2-methylpropyl)benzene-1,2-diol and 3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-pheny

Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives

Synthesis of a focussed library of trans-stilbene compounds through Wittig and other base catalysed condensation reactions is presented. The synthesized stilbenes were screened for their inhibitory potential against murine tyrosinase activity to explore the structure activity relationship (SAR). Presence of electron withdrawing group (-CN) at the double bond and hydroxyl group or halogen atom especially at para-position on the aromatic rings was found to significantly elevate the inhibitory activity. Among all the compounds screened, compounds 2, 6, 8, 10, 11, 15 and 21 were found to exhibit appreciable inhibitory activity. Compound 21 ((E)-2,3-bis(4-Hydroxyphenyl)acryonitrile) was found to be the most active with an IC50 value of 5.06 μM which is less than half of the value 10.78 μM observed for resveratrol (common standard used in murine tyrosinase activity studies) under similar conditions. The results obtained from the present study reveal structural/functional group sensitivity for the tyrosinase inhibitory activity of stilbenoid moieties and are expected to be very helpful for the design and synthesis of novel, selective and effective tyrosinase inhibitors.

Total Synthesis of Phenanthroindolizidine Alkaloids by Combining Iodoaminocyclization with Free Radical Cyclization

A concise and modular synthesis of phenanthroindolizidine alkaloids was achieved by combining iodoaminocylization with a free radical cyclization approach. The route described allowed the preparation of (±)-tylophorine, (±)-antofine, and (±)-deoxypergularinine in six steps. When commercially available l-prolinol was used as a chiral building block, (S)-(+)-tylophorine was also synthesized in 49% yield and >99% ee over five linear steps.

Design, synthesis and biological evaluation of 1-phenanthryl-tetrahydroisoquinoline derivatives as novel p21-activated kinase 4 (PAK4) inhibitors

Functional versatility and elevated expression in cancers have promoted p21-activated kinase 4 (PAK4) as one of the first-in-class anti-cancer drug targets. In this study, a series of novel 1-phenanthryl-tetrahydroisoquinoline analogues have been designed and synthesized as a novel class of small-molecule PAK4 inhibitors to fit into the cavity of PAK4. All of the target compounds were evaluated for their in vitro PAK4 inhibitory activities and antiproliferative activities. Lead optimization identified all the derivatives with more potency than the lead compound, especially compound 21a. Moreover, compound 21a significantly induced the cell cycle in the G1/S phase, and inhibited migration and invasion of MCF-7 cells via the regulation of the PAK4-LIMK1-cofilin signaling pathway. A molecular modeling study showed possible novel binding modes between 21a and PAK4 and provided a structural basis for further structure-guided design of PAK4 inhibitors.

Rhodium(III)-catalyzed intramolecular annulation through C-H activation: Total synthesis of (±)-antofine, (±)-septicine, (±)-tylophorine, and rosettacin

Annulation: The efficient synthesis of 3-hydroxyalkyl isoquinolones and 6-hydroxyalkyl 2-pyridones is enabled through the intramolecular annulation of alkyne-tethered hydroxamic esters (see scheme, Cp= pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional-group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant.

Iron(III) chloride-based mild synthesis of phenanthrene and its application to total synthesis of phenanthroindolizidine alkaloids

Iron(III) chloride has been used to prepare polymethoxy-substituted phenanthrene-9-carboxylic acid via intramolecular oxidative coupling at room temperature in excellent yields. Mild reaction conditions and the use of environmentally friendly FeCl3/

Total synthesis of phenanthroindolizidine alkaloids (±)-antofine, (±)-deoxypergularinine, and their dehydro congeners and evaluation of their cytotoxic activity

Due to their limited natural abundance and significant biochemical effects, we synthesized the alkaloids (±)-antofine (1a), (±)-deoxypergularinine (1b), and their dehydro congeners (2 and 3) starting from the corresponding phenanthrene-9-carboxaldehydes.

Synthesis and biological evaluation of some enantiomerically pure C8cC15 monoseco analogues of the phenanthroquinolizidine-type alkaloids cryptopleurine and julandine

A series of enantiomerically pure C8cC15 monoseco analogues, 2330, of the alkaloids cryptopleurine (1) and julandine (2) have been prepared using cinnamyl chloride 37 and (S)- or (R)-2-methylpiperidine as key building blocks. Two related compounds, 31 and

C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties

Four enantiomerically pure monoseco-analogues, 5, 7, 9, and 11, of the phenanthroquinolizidine alkaloid julandine (1) and four of congener cryptopleurine (2), viz. compounds 6, 8, 10, and 12, have been prepared and subjected to preliminary biological eval