61599-76-6

Upstream product

• 35274-53-4 2-bromo-3,4,5-tri-methoxybenzaldehyde 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 1035933-58-4 6-formyl-2,3,4-trimethoxyphenylboronic acid 
• 94838-88-7 2-formyl-4,5-(methylenedioxy)benzeneboronic acid 
• 58343-52-5 cyclohexyl-(6-iodo-benzo[1,3]dioxol-5-ylmethylene)-amine 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 73252-56-9 (2-bromo-3,4,5-trimethoxy-benzylidene)-cyclohexylamine 

Downstream Products

• 1034742-67-0 (6-(6-(hydroxymethyl)-2,3,4-trimethoxyphenyl)benzo[d][1,3]dioxol-5-yl)methanol 
• 1084695-41-9 C₁₈H₁₈N₂O₇ 

Relevant academic research and scientific papers

Discovery of novel antitumor dibenzocyclooctatetraene derivatives and related biphenyls as potent inhibitors of NF-κB signaling pathway

Several dibenzocyclooctatetraene derivatives (5-7) and related biphenyls (8-11) were designed, synthesized, and evaluated for inhibition of cancer cell growth and the NF-κB signaling pathway. Compound 5a, a dibenzocyclooctatetraene succinimide, was discovered as a potent inhibitor of the NF-κB signaling pathway with significant antitumor activity against several human tumor cell lines (GI50 1.38-1.45 μM) and was more potent than paclitaxel against the drug-resistant KBvin cell line. Compound 5a also inhibited LPS-induced NF-κB activation in RAW264.7 cells with an IC50 value of 0.52 μM, prevented IκB-α degradation and p65 nuclear translocation, and suppressed LPS-induced NO production in a dose-dependent manner. The antitumor data in cellular assays indicated that relative positions and types of substituents on the dibenzocyclooctatetraene or acyclic biphenyl as well as torsional angles between the two phenyls are of primary importance to antitumor activity.

Tubulin-binding dibenz[c,e]oxepines as colchinol analogues for targeting tumour vasculature

Various methoxy- and hydroxy-substituted dibenz[c,e]oxepines were prepared via the copper(i)-induced coupling of ether-tethered arylstannanes or the dehydrative cyclisation of 1,1′-biphenyl-2,2′-dimethanols, assembled using the Ullmann cross-coupling of ortho-bromoaryl carbonyl compounds. The dibenzoxepines were screened for their ability to inhibit tubulin polymerisation and the in vitro growth of K562 human chronic myelogenous leukemia cells. The most active was 5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol, whose tubulin inhibitory and cytotoxicity (IC50) values were 1 μM and 40 nM, respectively.

Synthesis of unsymmetrical biphenyls as potent cytotoxic agents

Twenty-six unsymmetrical biphenyls were synthesized and evaluated for cytotoxic activity against DU145, A549, KB and KB-Vin tumor cell lines. Three compounds 27, 35 and 40 showed very potent activity against the HTCL panel with an IC50 value range of 0.04-3.23 μM. In addition, fourteen active compounds were all more potent against the drug-resistant KB-Vin cell line than the parental KB cell line. Preliminary SAR analysis indicated that two bulky substituents on the 2,2′-positions of unsymmetrical biphenyl skeleton are necessary and crucial for in vitro anticancer activity, thus providing a good starting point to develop unsymmetrical biphenyls as novel anticancer agents.

SYNTHESES TOTALES ET ETUDES DE LIGNANES BIOLOGIQUEMENT ACTIFS-I. APPLICATION DE LA REACTION D'ULLMANN A LA SYNTHESE DE BIARYLES PRECURSEURS DE LIGNANES BISBENZOCYCLOOCTADIENES

Several biaryls bearing various substituents on both rings were synthesized in a preparativ fashion, and in yields up to 88percent by a technical improvement on the classical Ullmann reaction.All these biaryls bear reactive functional groups (i.e. formyl, methoxycarbonyl, dimethoxycarbonylpropyl and butanolidylmethyl) in both the o and o' positions.The biaryls 9, 13, 21 and 26-33 are plausible synthons for bisbenzocyclooctadiene lignans such as schizandrin and steganacin.

The Ambient Temperature Ullmann Reaction and Its Application to the Total Synthesis of (+/-)-Steganacin

The details of a new method for preparing unsymmetrical biphenyls at room temperature by a modification of the classical Ullmann reaction are discussed.An intramolecularly coordinated organocopper reagent is treated with an aryl iodide bearing a potential coordinating ligand to form the biphenyl.Nitrogen and sulfur have been utilized as ligands and as protecting groups for carbonyls.The application of this methodology to the synthesis of the antileukemic steganacin is detailed.