63558-07-6

Upstream product

• 67-66-3 chloroform 
• 103-90-2 4-acetaminophenol 
• 7726-95-6 bromine 
• 101251-09-6 (4-acetylaminophenyl)boronic acid 
• 19628-79-6 2,6-dibromo-4-nitrosophenol 
• 609-21-2 2,6-dibromo-4-aminophenol 
• 108-24-7 acetic anhydride 

Downstream Products

• 1355597-90-8 5-(1-(3,5-dibromo-4-methoxyphenyl)-1H-tetrazol-5-yl)-2-methoxyphenol 
• 1355597-84-0 5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-dibromo-4-methoxyphenyl)-1H-tetrazole 
• 1355597-78-2 3-((tert-butyldimethylsilyl)oxy)-N-(3,5-dibromo-4-methoxyphenyl)-4-methoxybenzothioamide 
• 1355597-71-5 3-((tert-butyldimethylsilyl)oxy)-N-(3,5-dibromo-4-methoxyphenyl)-4-methoxybenzamide 
• 108761-48-4 N-(3,5-dibromo-4-methoxyphenyl)acetamide 
• 41727-70-2 3,5-dibromo-4-methoxyaniline 
• 1363602-98-5 5-azido-1,3-dibromo-2-methoxybenzene 
• 1380079-65-1 C₂₈H₄₁Br₂N₃O₄Si₂ 
• 1380079-58-2 C₂₂H₂₇Br₂N₃O₃Si 
• 1380079-55-9 C₂₂H₂₇Br₂N₃O₃Si 
• 1363603-30-8 3-(1-(3,5-dibromo-4-methoxyphenyl)-1H-1,2,3-triazol-5-yl)-6-methoxybenzene-1,2-diol 
• 1363603-26-2 2-(1-(3,5-dibromo-4-methoxyphenyl)-1H-1,2,3-triazol-5-yl)-5-methoxyphenol 
• 1363603-20-6 5-(1-(3,5-dibromo-4-methoxyphenyl)-1H-1,2,3-triazol-5-yl)-2-methoxyphenol 

Relevant academic research and scientific papers

A scalable and green one-minute synthesis of substituted phenols

A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso-hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H2O2/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.

Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A-1

The antiproliferative activity on ovarian cancer (SK-OV-3) cells of a series of triazole-bridged combretastatin analogues (37, 38, 40-43) containing dihalogenation of the A-ring is reported, and compared with their trimethoxy analogues (5, 15, 39). It was found that dihalogenation with either bromine or iodine was a tolerated modification when compared to the parent compound combretastatin (CA-4, 1) and had less effect than B-ring modification on potency. These compounds exhibited G2/M arrest, and maintained antitubulin activity. Further assays on human umbilical vein endothelial cells (HUVECs) demonstrated the potential antivascular effects of these triazoles. Of particular note was a 3,5-diiodo-4-methoxyaryl triazole (43) which had promising 7-fold selectivity for HUVECs over ovarian cancer cells.

A-ring dihalogenation increases the cellular activity of combretastatin-templated tetrazoles

The combretastatins have been investigated for their antimitotic and antivascular properties, and it is widely postulated that a 3,4,5-trimethoxyaryl A-ring is essential to maintain potent activity. We have synthesized new tetrazole analogues (32a€"34), demonstrating that 3,5-dihalogenation can consistently increase potency by up to 5-fold when compared to the equivalent trimethoxy compound on human umbilical vein endothelial cells (HUVECs) and a range of cancer cells. Moreover, this increased potency offsets that lost by installing the tetrazole bridge into combretastatin A-4 (1), giving crystalline, soluble compounds that have low nanomolar activity, arrest cells in G2/M phase, and retain microtubule inhibitory activity. Molecular modeling has shown that optimized packing within the binding site resulting in increased Coulombic interaction may be responsible for this improved activity.

COMPOUNDS AND THERAPEUTICAL USE THEREOF

Disclosed are 4-arylamino-quinazolines and analogs thereof effective as activators of caspases and inducers of apoptosis. The compounds of this invention are useful in the treatment of a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.