24316-12-9

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 55733-81-8 2,3-di-(3,4-dimethoxyphenyl)propanoic acid 
• 7575-08-8 4-[(Z)-2-(3,4-dimethoxyphenyl)vinyl]-1,2-dimethoxybenzene 
• 121194-88-5 (E)-2,3-bis-(3,4-dimethoxyphenyl)-N-(3-formylpropyl)acrylamide 
• 101537-87-5 (E)-N-(4,4-diethoxybutyl)-2,3-bis-(3,4-dimethoxyphenyl)-acrylamide 
• 101537-88-6 (E)-6-[(E)-2,3-Bis-(3,4-dimethoxy-phenyl)-acryloylamino]-hex-2-enoic acid ethyl ester 
• 35676-02-9 2,3,6,7-tetramethoxy-phenanthrene-9-carboxylic acid 
• 25908-89-8 methyl (E)-3,4-dimethoxy-α-(3',4'-dimethoxyphenylmethylene)benzeneacetate 
• 482-20-2 (S)-(+)-tylophorine 
• 26503-67-3 (+/-)-6,7-di(3,4-dimethoxyphenyl)-1,2,3,5,8,8a-hexahydro-indolizine 
• 156424-91-8 6,7-bis-(3,4-dimethoxyphenyl)-1,2,3-trihydroindolizine-5-one 
• 1360803-81-1 (E)-3,4-bis(3,4-dimethoxyphenyl)but-3-en-2-one 
• 1360803-82-2 (E)-1,2-bis(3,4-dimethoxyphenyl)hept-1-en-3-one 
• 18513-98-9 3,4,3',4'-Tetramethoxystilben 

Relevant academic research and scientific papers

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.

Racemization-free synthesis of (S)-(+)-tylophorine from l -proline by radical cyclization

Figure presented The phenanthroindolizidine alkaloid (S)-(+)-tylophorine was synthesized from l-proline in nine linear steps including a double bromination and a free-radical cyclization of an N-aziridinylimine as the key steps. The phenanthrene moiety was prepared from homoveratric acid and veratraldehyde and permits the variation of each oxygen-substituted ring.

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.

Aerobic Oxidative Intramolecular Aromatic Coupling via Heterogeneous Metal Catalysts

An aerobic, heterogeneously catalyzed oxidative intramolecular coupling reaction of aromatic compounds is reported here. Using commercially available, recyclable heterogeneous metal catalysts, the coupling reactions of o-terphenyls and 1,ω-biarylalkanes proceeded quickly under mild conditions, i.e., at room temperature under oxygen as a co-oxidant almost all within 1 h, to provide the corresponding coupled products like triphenylenes and phenanthrenes in good to excellent yields. This reaction is an easily handled, practical, and atom-economical coupling method, which is of great importance in modern organic syntheses. (Figure presented.).

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.

Oxidative intramolecular coupling of 2,3-disubstituted phenyl acrylic acids and derivatives promoted by di-tert-butylperoxide

Polymethoxy-substituted phenanthrene-9-carboxylic acids or their methylate are key intermediates for the synthesis of tylophora alkaloids and their analogs. An intramolecular oxidative coupling reaction of unfunctionalized 2,3-disubstituted phenyl acrylic

Iron(III) chloride catalyzed oxidative coupling reaction of 1,2-diarylethylene derivatives

A nontoxic FeCl3 catalyzed intramolecular oxidative coupling reaction was developed for mild synthesis of a series of phenanthrenes with different substituents. The method involves cross dehydrogenative coupling of a variety of 1,2-diarylethyle

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.

A simple and efficient oxidative coupling of aromatic nuclei mediated by manganese dioxide

Oxidative intramolecular coupling of the aryl rings of various stilbenes for direct construction of the phenanthrene ring system is promoted efficiently by manganese dioxide-trifluoroacetic acid at room temperature in excellent yields. This approach is also applied to the intermolecular biaryl coupling of 2-naphthols, 2-naphthalenethiol, 2-naphthylamine, a phenol ether and a phenol under very mild conditions. An electron-transfer mechanism is proposed in which manganese dioxide acts as a two-electron oxidant.

Synthesis and antitumor activities of phenanthrene-based alkaloids

A series of phenanthrene-based tylophorine derivatives (PBTs) were synthesized and their cytotoxic activities against the H460 human large-cell lung carcinoma cell line were evaluated. Among these compounds, N-(3-hydroxy-2,6,7-tri-methoxyphenanthr-9-ylmet