87101-67-5

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 87101-68-6 (E)-2-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)-acrylic acid methyl ester 

Relevant academic research and scientific papers

Boehmeriasin A as new lead compound for the inhibition of topoisomerases and SIRT2

Two synthetic approaches to boehmeriasin A are described. A gram scale racemic preparation is accompanied by an efficient preparation of both the pure enantiomers using the conformationally stable 2-piperidin-2-yl acetaldehyde as starting material. The an

Total Synthesis of Phenanthropiperidine Alkaloids by Sequential Alkylation of N,N-Dibenzylaminoacetonitrile

Two representative members of the phenanthropiperidine alkaloid family, tylophorine (1) and cryptopleurine (2), were synthesized by a bidirectional alkylation strategy employing dibenzylaminoacetonitrile as a substrate. This approach relies on the unprecedented condensation of metallated α-aminonitriles with bromomethylphenanthrenes to provide fully substituted α-aminonitriles, which are subjected to a NaBH4-mediated reductive decyanation process to form homobenzylic amines. From these intermediates, a terminal leaving group was introduced by simple chemical manipulation, and its displacement by a free primary amine under two favorable cyclization processes led to the formation of the future E-ring of both alkaloids in high yields. Finally, a late Pictet-Spengler cyclization ensured the formation of a D-ring for the alkaloids 1 and 2.

Advances in the 1-phenanthryl-tetrahydroisoquinoline series of PAK4 inhibitors: Potent agents restrain tumor cell growth and invasion

A new series of novel 1-phenanthryl-tetrahydroisoquinoline derivatives were designed, synthesized and biologically evaluated for their PAK4 inhibitory activities and anti-proliferative effects against three cancer cell lines A549, MCF-7 and HT-1080. Among them, compound 12a exhibited the most potent inhibitory activity against PAK4 with an IC50 value of 0.42 μM. Moreover, this compound inhibited the invasion of A549 tumor cells by regulating the PAK4-LIMK1-cofilin signaling pathway in vitro, and exhibited anti-tumor activity in vivo in the A549 tumor xenograft model. To further evaluate the binding mode of 12a with PAK4, the biotinylated 12a derivative has been synthesized and it was used for immunoprecipitation assay. Intriguingly, our observations suggest that 12a interacts with both the N- and C-termini of PAK4.

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.

Synthesis and biological evaluation of tylophorine-derived dibenzoquinolines as orally active agents: Exploration of the role of tylophorine e ring on biological activity

A series of novel tylophorine-derived dibenzoquinolines has been synthesized and their biological activity evaluated. Three assays were conducted: inhibition of cancer cell proliferation, inhibition of TGEV replication for anticoronavirus activity, and su

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.

Quinolizidine Alkaloid Synthesis via the Intramolecular Imino Diels-Alder Reaction. epi-Lupinine and Cryptopleurine

A totally stereoselective total synthesis of epi-lupinine (1) has been developed that starts with methyl sorbate (6).Alkylation of 6 with bromide 8 gave diene 10, which was elaborated into the imino Diels-Alder precursor 17.Thermolysis of 17 provided excl