94483-71-3

Upstream product

• 43060-63-5 2-(dimethylaminomethyl)-6-methoxyphenol 
• 90704-69-1 N,N-dimethyl-2,3-dimethoxybenzylamine 
• 50-00-0 formaldehyd 
• 120-80-9 benzene-1,2-diol 
• 124-40-3 dimethyl amine 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 90-05-1 2-methoxy-phenol 

Relevant academic research and scientific papers

Synthesis of functional catechols as monomers of mussel-inspired biomimetic polymers

Catechol-containing polymers have attracted much attention in recent years because of their versatile mussel-inspired adhesive function. We report herein the facile synthesis of 4-/3-substituted catechols using the Mannich reaction of catechol with formaldehyde and secondary amines. The reaction proceeds smoothly in water without any catalyst. Separation of the desired products is important for the success of this methodology, and was achieved by a pH-controlled solvent extraction and recrystallization process. The synthesized functional catechols not only exhibited dopamine-like oxidative cross-linking, but also possessed functional groups that are useful for the synthesis of catechol-containing polymers. As a proof-of-concept application, two functional catechols, one bearing monohydroxyl and the other bearing dihydroxyl groups at the 4-aminomethyl substituent, were incorporated into polyacrylate and polyurethane backbones, respectively, endowing these polymers with excellent coatability on various surfaces.

Catechol derivative as well as synthesis and application of biomimetic polymer of catechol derivative

The invention discloses a synthetic method and application of a catechol derivative and a biomimetic polymer, which belongs to the field of macromolecule biological materials and functional materials.Catechol, formaldehyde and secondary amine, which are low in price and easy to acquire, are used as raw materials to obtain 4-amine methyl substituted catechol derivative and 3-amine methyl substituted catechol derivative by virtue of mannich reaction. The biomimetic polymer is the biomimetic polymer comprising catechol polyurethane or the biomimetic polymer comprising catechol polyacrylate, andpolymer monomers are prepared into the biomimetic polymer comprising a catechol structure by virtue of addition polymerization or radical polymerization. The catechol derivative obtained by the methodprovided by the invention can be used for synthesizing the biomimetic polymer comprising the catechol structural unit; and the biomimetic polymer synthesized from the catechol derivative has excellent coating forming capability, protein adsorption resistant capability and hydrogel forming capability and has application value in the aspects such as medical adhesive, medical hydrogel, and coating materials.

Controlled synthesis of novel dibenzene-1,2-diol mannich bases

The synthesis of a number of novel dibenzene-1,2-diol Mannich bases can be achieved in good yields by the condensation of 2-methoxyphenol, formaldehyde and secondary diamines. The newly developed synthetic method utilizes 2-methoxyphenol instead of benzen

Inhibition and inactivation of presynaptic cholinergic markers using redox-reactive choline analogs

Inhibition and inactivation of two presynaptic cholinergic 'markers', choline acetyltransferase and high affinity choline transporter, has been investigated using inhibitors designed with a redox-reactive catechol tethered to a quaternary ammonium group. Two quaternary ammonium alkyl- substituted catechols, 3[(trimethylammonio)methyl]catechol (TMC, 1) and N,N- dimethylepinephrine (catecholine, 2) were shown to bind weakly and noncompetitively to bovine choline acetyltransferase yet inactivated the enzyme in a time course consistent with the involvement of early intermediates in the spontaneous oxidation of these catechols. Both agents also inhibited high-affinity choline uptake. The time course of TMC and catecholine spontaneous oxidation-dependent inactivation of high affinity choline uptake sites was slower than, if it occurred at all, the spontaneous degradation of measurable choline transport in synaptosomes. When compared with inhibition of uptake of other neurotransmitters, it was shown that catecholine demonstrated more selectivity than TMC toward inhibition of choline transport. K(m) (μM) and V(max) (pmol/min per mg of protein) were measured for high affinity transport of choline, dopamine, and serotonin and were observed to be K(m) = 2.04 ± 0.31, V(max) = 22 ± 1; K(m) = 1.4, V(max) = 53; and K(m) = 0.15, V(max) = 23, respectively, in good agreement with published literature values. K(i)'s (mM) for catecholine and TMC, calculated from experimentally determined IC50's, were for catecholine 0.13 ± 0.06, 0.53 ± 0.09, and 0.39 ± 0.10, and for TMC 0.06 ± 0.03, 0.09 ± 0.03, and 0.09 ± 0.08, for choline, dopamine, and serotonin transport, respectively. In vivo studies using catecholine suggest that this compound impairs learning ability associated with long-term memory. Thus, catecholine represents a lead compound in a potential series of redox-reactive choline analogs, which may become useful irreversible antagonists of the critical cholinergic macromolecular targets underlying cholinergic hypofunction in disorders such as Alzheimer's disease.