1170045-84-7

Upstream product

• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 1067880-35-6 tert-butyl(2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)vinyl)phenoxy)dimethylsilane 
• 1070196-57-4 C₁₈H₂₁O₈P 
• 1070196-46-1 isocombretastatin A-1 
• 1070196-13-2 C₂₃H₂₉NO₆ 
• 1067880-33-4 1,2,3-trimethoxy-5-(1-(p-tolyl)vinyl)benzene 
• 1067880-34-5 2-[1-(3,4,5-trimethoxyphenyl)vinyl]naphthalene 
• 1067880-32-3 1,2,3-trimethoxy-5-(1-(4-methoxyphenyl)vinyl)benzene 
• 1067880-36-7 C₂₀H₂₂O₆ 
• 1070195-79-7 5-(1-(3-fluoro-4-methoxyphenyl)vinyl)-1,2,3-trimethoxybenzene 
• 1067880-31-2 isocombretastatin A₄ 

Relevant academic research and scientific papers

Pyrrolo-imidazo[1,2- A[pyridine Scaffolds through a Sequential Coupling of N-Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application

A new strategy for the construction of 3-phenyl-1H-pyrrolo-imidazo[1,2-a]pyridine backbone is described. The reaction starts from the coupling between N-tosylhydrazones and 2-chloro-3-nitroimidazo[1,2-a]pyridines leading to the formation of 3-nitro-2-(ary

Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System

A green Barluenga-Valdés cross-coupling reaction for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos-SO3Na or Pd/MeDavephos-CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its activity.

A fluorine scan of a tubulin polymerization inhibitor isocombretastatin A-4: Design, synthesis, molecular modelling, and biological evaluation

A novel series of tubulin polymerization inhibitors, based on fluorinated derivatives of isocombretastatin A-4 was synthesized with the goal of evaluating the effect of these compounds on the proliferative activity. The introduction of fluorine atom was performed on the phenyl ring or at the linker between the two aromatic rings. The modification of isoCA-4 by introduction of difluoromethoxy group at the para-position (3i) and substitution of the two protons of the linker by two fluorine atoms (3m), produced the most active compounds in the series, with IC50 values of 0.15–2.2 nM (3i) and 0.1–2 nM (3m) respectively, against a panel of six cancer cell lines. Compounds 3i and 3m had greater antiproliferative activity in comparison with references CA-4 or isoCA-4, the presence of fluorine group leads to a significant enhancement of the antiproliferative activity. Molecular docking studies indicated that compounds 3i and 3m occupy the colchicine binding site of tubulin. Evaluation of cytotoxicity in Human noncancer cells indicated that the compounds 3i and 3m were practically ineffective in quiescent peripheral blood lymphocytes, and may have a selective antiproliferative activity against cancer cells. Analyses of cell cycle distribution, and morphological microtubules organization showed that compound 3m induced G2/M phase arrest and, dramatically disrupted the microtubule network.

Design and Synthesis of Tubulin and Histone Deacetylase Inhibitor Based on iso-Combretastatin A-4

Designing multitarget drugs have raised considerable interest due to their advantages in the treatment of complex diseases such as cancer. Their design constitutes a challenge in antitumor drug discovery. The present study reports a dual inhibition of tub

Palladium-Catalyzed One-Pot Synthesis of 5-(1-Arylvinyl)-1H-benzimidazoles: Overcoming the Limitation of Acetamide Partners

A new one-pot palladium-catalyzed process between N-tosylhydrazones, N-(dihalophenyl)-imidates, and amines was designed. This reaction involves Barluenga cross-coupling and N-arylation followed by cyclization to produce functionalized benzimidazoles. Duri

IsoCombretaQuinazolines: Potent Cytotoxic Agents with Antitubulin Activity

A series of novel isocombretaquinazolines (isoCoQ) 4 were quickly prepared by coupling N-toluenesulfonylhydrazones with 4-chloroquinazolines under palladium catalysis. These compounds, which can be regarded as isocombretastatin A-4 (isoCA-4) analogues tha

Tandem one-pot palladium-catalyzed coupling of hydrazones, haloindoles, and amines: Synthesis of amino-N-vinylindoles and their effect on human colon carcinoma cells

The synthesis of amino-substituted N-vinylazoles was achieved by a new palladium-assisted tandem catalytic reaction involving N-tosylhydrazones, halo-substituted azoles, and amines. Accordingly, two Csp2-N bonds were formed through two mechanistically distinct reactions using a single PdII/Pd0 catalyst system in a one-pot fashion. This work paves the way for the design of biological relevant compounds in an amino-substituted N-vinylindole series. Among several polyoxygenated derivatives evaluated, compounds 5e and 5u were found to exhibit good antiproliferative activity.

Synthesis of a 3-(α-Styryl)benzo[ b ]-thiophene Library via Bromocyclization of Alkynes and Palladium-Catalyzed Tosylhydrazones Cross-Couplings: Evaluation as Antitubulin Agents

A library of functionalized 3-(α-styryl)-benzo[b]thiophenes, endowed with a high level of molecular diversity, was efficiently synthesized by applying a synthetic sequence that allowed introduction of various substituents on aromatic A, B, and C-rings. Th

Catalytic three-component one-pot reaction of hydrazones, dihaloarenes, and amines

A new three-component assembly reaction between N-tosylhydrazones, dihalogenated arenes, and various primary and secondary amines was devised, producing nitrogen-containing 1,1'-diarylethylenes in good yields. The two C-C and C-N bonds formed through this

An efficient coupling of N-tosylhydrazones with 2-halopyridines: Synthesis of 2-α-styrylpyridines endowed with antitumor activity

The synthesis of 2-α-styrylpyridines has been carried out by using the coupling of polyoxygenated N-tosylhydrazones with various 2-halopyridines. We demonstrated that the use of a catalytic amount of PdCl2(MeCN) 2 in combination with a bidentate ferrocene DPPF or a monodentate alkyl phosphine tBu2MeP-HBF4 constitutes an efficient protocol for this coupling, providing 2-α-styrylpyridines 2 in satisfactory to good yields. Among several polyoxygenated derivatives 2 evaluated, compound 2aa was found to exhibit excellent antiproliferative and antimitotic activities comparable to that of the reference compound isoCA-4. The Royal Society of Chemistry 2013.