138076-70-7

Upstream product

• 19463-48-0 5-chlorovanillin 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 121-33-5 vanillin 

Downstream Products

• 1365030-58-5 O-benzyl N-(6-chloro-2,5-dioxo-4-methoxy-1,4-cyclohexadienyl)-L-alanine 
• 1380401-60-4 formic acid 4-(tert-butyldimethylsilanyloxy)-3-chloro-5-methoxyphenyl ester 
• 1365030-60-9 4-(tert-butyldimethylsilanyloxy)-3-chloro-5-methoxyphenol 
• 1365030-62-1 2-bromo-4-(tert-butyldimethylsilyloxy)-3-chloro-5-methoxyphenol 
• 1365030-56-3 2-bromo-3-chloro-5-methoxy-1,4-benzoquinone 
• 1365030-40-5 2-bromo-3-chloro-5-methoxy-1,4-dihydroxybenzene 
• 1470111-23-9 C₄₂H₅₁ClO₁₀Si 
• 1470111-31-9 C₃₆H₃₇ClO₁₀ 

Relevant academic research and scientific papers

The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands

A series of carbonate analogues of 5′-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with Ki(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism.

Redox potentials, laccase oxidation, and antilarval activities of substituted phenols

Laccases are copper-containing oxidases that are involved in sclerotization of the cuticle of mosquitoes and other insects. Oxidation of exogenous compounds by insect laccases may have the potential to produce reactive species toxic to insects. We investigated two classes of substituted phenolic compounds, halogenated di- and trihydroxybenzenes and substituted di-tert-butylphenols, on redox potential, oxidation by laccase and effects on mosquito larval growth. An inverse correlation between the oxidation potentials and laccase activity of halogenated hydroxybenzenes was found. Substituted di-tert-butylphenols however were found to impact mosquito larval growth and survival. In particular, 2,4-di-tert-butyl-6-(3-methyl-2-butenyl)phenol (15) caused greater than 98% mortality of Anopheles gambiae larvae in a concentration of 180 nM, whereas 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylpropanal oxime (13) and 6,8-di-tert-butyl-2,2-dimethyl-3,4-dihydro-2H-chromene (33) caused 93% and 92% mortalities in concentrations of 3.4 and 3.7 μM, respectively. Larvae treated with di-tert-butylphenolic compounds died just before pupation.