154083-41-7

Basic information

• Product Name: 3-((tert-butyldimethylsilyl)oxy)-4-methoxybenzoic acid
• Synonyms: 3-((tert-butyldimethylsilyl)oxy)-4-methoxybenzoic acid
• CAS NO: 154083-41-7
• Molecular Weight: 282.412
• Mol File: 154083-41-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3-((tert-butyldimethylsilyl)oxy)-4-methoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-((tert-butyldimethylsilyl)oxy)-4-methoxybenzoic acid(154083-41-7)
• EPA Substance Registry System: 3-((tert-butyldimethylsilyl)oxy)-4-methoxybenzoic acid(154083-41-7)

Safety Data

• Hazardous Substances Data: 154083-41-7(Hazardous Substances Data)

Upstream product

• 645-08-9 Isovanillic acid 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 621-59-0 isovanillin 
• 288-32-4 1H-imidazole 
• 97315-18-9 p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde 

Downstream Products

• 913985-11-2 3-(tert-butyl-dimethyl-silanyloxy)-N-(3,5-dichloro-pyridin-4-yl)-4-methoxy-benzamide 
• 144036-24-8 3-hydroxy-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide 
• 203448-31-1 N-[(3-tertbutyldimethylsilyl)oxy-4-methoxybenzoyl]morpholine 
• 203448-33-3 3-O-dibenzylphosphoryl-phenstatin 
• 229027-06-9 Phosphoric acid mono-[2-methoxy-5-(3,4,5-trimethoxy-benzoyl)-phenyl] ester 
• 203448-30-0 (3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone 
• 203448-32-2 phenstatin 
• 1355597-92-0 5-(1-(3,5-diiodo-4-methoxyphenyl)-1H-tetrazol-5-yl)-2-methoxyphenol 
• 1355597-86-2 5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-diiodo-4-methoxyphenyl)-1H-tetrazole 
• 1355597-80-6 3-((tert-butyldimethylsilyl)oxy)-N-(3,5-diiodo-4-methoxyphenyl)-4-methoxybenzothioamide 
• 1355597-74-8 3-((tert-butyldimethylsilyl)oxy)-N-(3,5-diiodo-4-methoxyphenyl)-4-methoxybenzamide 
• 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 

Relevant articles and documents

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.

AZOLE-BASED PHOSPHODIESTERASE INHIBITORS

The present invention relates to phosphodiesterase (PDE) type IV selective inhibitors. Processes for the preparation of disclosed compounds of Formula (I), pharmaceutical compositions containing the compounds described herein and their use as PDE type IV selective inhibitors are provided.

Antineoplastic agents. 379. Synthesis of phenstatin phosphate

A structure-activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A- 4 (1b) directed at maintaining the (Z)stilbene relationship of the olefin diphenyl substituents led to synthesis of a potent cancer cell growth inhibitor designated phenstatin (3b). Initially phenstatin silyl ether (3a) was unexpectedly obtained by Jacobsen oxidation of combretastatin A-4 silyl ether (1c → 3a), and the parent phenstatin (3b) was later synthesized (6a → 3a → 3b) in quantity. Phenstatin was converted to the sodium phosphate prodrug (3d) by a dibenzyl phosphite phosphorylation and subsequent hydrogenolysis sequence (3b → 3c → 3d). Phenstatin (3b) inhibited growth of the pathogenic bacterium Neisseria gonorrhoeae and was a potent inhibitor of tubulin polymerization and the binding of colchicine to tubulin comparable to combretastatin A-4 (1b). Interestingly, the prodrugs were found to have reduced activity in these biochemical assays. While no significant tubulin activity was observed with the phosphorylated derivative of combretastatin A- 4 (1d), phosphate 3d retained detectable inhibitory effects in both assays.