79338-84-4

Usage

Uses

Used in Dermatological Applications:
3,5-Dihydroxy-4-isopropylstilbene is used as a therapeutic agent for the treatment of psoriasis and atopic dermatitis. Clinical trials conducted abroad have shown that Benzenemod cream, containing Tapinarof, has good efficacy and safety on atopic dermatitis and psoriasis. In China, as a class 1.1 new drug, Benzenemod cream has undergone phase I-II clinical trials, and the results show that it has good efficacy and safety for plaque psoriasis.

Biological activity

Tapinarof(GSK2894512) is a natural agonist of aryl hydrocarbon receptor (AhR) that induces nuclear translocation of AhR in immortalized keratinocytes (HaCaT) with EC50 of 0.16 nM. Benvitimod induces apoptosis in CD4+ T cells in a dose-dependent manner with an IC50 value of 5.2 μM.

InChI:InChI=1/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+

Upstream product

• 141509-20-8 (E)-1,3-dimethoxy-2-(1-methylethyl)-5-(2-phenylethenyl)benzene 
• 2040-04-2 2,6-dimethoxyacetophenone 
• 16700-61-1 1,3-dimethoxy-2-(1-methylethyl)benzene 
• 16929-70-7 1,3-dimethoxy-2-(1-hydroxy-1-methylethyl)benzene 
• 25108-61-6 1,3-dimethoxy-2-(1-methylethenyl)benzene 
• 2323519-79-3 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]-1,3-cyclohexanedione 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 122-03-2 (4-isopropylbenzaldehyde) 
• 344396-19-6 3,5-dimethoxy-4-(1-methylethyl)benzaldehyde 
• 344396-18-5 4-isopropyl-3,5-dimethoxy-benzyl alcohol 
• 115781-08-3 3,5-dihydroxy-4-isopropyl stilbene 
• 1622988-14-0 (Z)-3,5-dihydroxy-4-isopropylstilbene 
• 4670-09-1 2-(3,5-dihydroxyphenyl)acetic acid 

Downstream Products

• 344396-15-2 3,5-Di-chloroacetoxy-4-isopropyl-trans-stilbene 

Relevant academic research and scientific papers

Preparation method of benzenediol bioactive substance

The invention discloses a preparation method of a benzenediol bioactive substance, and belongs to the technical field of organic synthesis. The method comprises the following steps: reacting 4-isopropyl-3, 5-dimethoxybenzyl alcohol with triethyl phosphite

Synthesis method of (E)-3,5-dihydroxy-4-isopropyl stilbene

The invention discloses a synthesis method of (E)-3,5-dihydroxy-4-isopropyl stilbene, which comprises the following steps: by using a biomass-derived raw material 3,5-dihydroxy-2,4-diethoxycarbonyl ethyl phenylacetate as an initiator, carrying out hydrolysis decarboxylation, isopropylation, condensation, decarboxylation, isomerization and other reaction steps to synthesize the (E)-3,5-dihydroxy-4-isopropyl stilbene. In the invention, the biomass derivative raw materials can be adopted as initiators, operation is easy and convenient, the steps are simple and convenient, functional group protection and deprotection are not needed, and atom economy is good; the intermediate can be put into the next step of reaction without complex separation and purification, so that large-scale preparation is facilitated; and the generated excessive waste acid and catalyst compound can be recycled, so that the cost of the technological process is reduced, the emission is reduced, and the method is greenand environment-friendly.

PROCESS FOR PREPARING TAPINAROF

The present invention provides processes for the preparation of 3, 5-Dihydroxy-4-isopropyl-trans-stilbene or a salt or solvate thereof and novel intermediates used therein. In some embodiments the 3, 5-Dihydroxy-4-isopropyl-trans-stilbene is prepared from

Method for preparing 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol

The invention provides a method for preparing 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol, belongs to the technical field of medicine preparation and particularly provides a simple method for preparing 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol. The method includes the following steps that 4-isopropylbenzaldehyde serves as the starting material, 3,5-dibromo-4-isopropylbenzaldehyde is obtained through 3,5 position bromination, 3,5-dimethoxy-4-isopropylbenzaldehyde is synthesized with sodium methoxide, then 3,5-dyhydroxy-4-isopropylbenzaldehyde is obtained through demethylation with pyridine, 3,5-dialkyl ester-4-isopropylbenzaldehyde is obtained through esterification, 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol protected by carbethoxy is obtained through wittig reaction, and the target compound, namely 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol, is obtained through hydrolysis reaction. The method has the advantages that the number of reaction steps is small, reaction conditions are mild and industrialization is easy, and can meet the synthesis requirement of 2-(1-methylethyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol raw materials.

Facile synthesis of cyclohexanediones and dialkylresorcinols - Bioactive natural products from entomopathogenic bacteria

A synthesis for the recently identified, widespread bacterial natural product classes of dialkylresorcinols and cyclohexanediones was developed. The synthesis route is similar to the biosynthesis route in that the formation of the cyclohexanedione ring results from two parts, as exemplified by the synthesis of the multifunctional isopropylstilbenes identified in Photorhabdus luminescens. Testing of these compounds revealed good bioactivity against Trypanosoma brucei rhodesiense and T. cruzi, the causative agents of sleeping sickness and Chagas disease, respectively.