61599-76-6

Basic information

• Product Name: 1,3-Benzodioxole-5-carboxaldehyde, 6-(6-formyl-2,3,4-trimethoxyphenyl)-
• CAS NO: 61599-76-6
• Molecular Formula: C18H16O7
• Molecular Weight: 344.321
• Mol File: 61599-76-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3-Benzodioxole-5-carboxaldehyde, 6-(6-formyl-2,3,4-trimethoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzodioxole-5-carboxaldehyde, 6-(6-formyl-2,3,4-trimethoxyphenyl)-(61599-76-6)
• EPA Substance Registry System: 1,3-Benzodioxole-5-carboxaldehyde, 6-(6-formyl-2,3,4-trimethoxyphenyl)-(61599-76-6)

Safety Data

• Hazardous Substances Data: 61599-76-6(Hazardous Substances Data)

Upstream product

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

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 articles and documents

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.

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.

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.