26050-64-6

Usage

Uses

Used in Organic Synthesis:
Methyl 4-bromo-3,5-dimethoxybenzoate is utilized as a building block in organic synthesis for the preparation of more complex molecules. Its unique structure allows for the creation of a variety of chemical entities, making it an essential component in the synthesis process.
Used in Pharmaceutical Manufacturing:
As a versatile intermediate, methyl 4-bromo-3,5-dimethoxybenzoate is employed in the manufacturing of pharmaceuticals. Its role in the synthesis of various drugs contributes to the development of new medications and therapies.
Used in Agrochemical Production:
Methyl 4-bromo-3,5-dimethoxybenzoate also serves as an intermediate in the production of agrochemicals. Its application in this industry aids in the development of pesticides, herbicides, and other agricultural chemicals to improve crop protection and yield.
Used in Pharmacological Research:
Methyl 4-bromo-3,5-dimethoxybenzoate is studied for its potential pharmacological properties, including its activity as an agonist for certain serotonin receptors in the brain. This research could lead to the discovery of new treatments for neurological and psychiatric disorders.

InChI:InChI=1/C10H11BrO4/c1-13-7-4-6(10(12)15-3)5-8(14-2)9(7)11/h4-5H,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 56518-42-4 4-bromo-3,5-dimethoxybenzoic acid 
• 16534-12-6 3,5-dihydroxy-4-bromobenzoic acid 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 56518-43-5 4-bromo-3,5-dimethoxybenzoyl chloride 
• 74-88-4 methyl iodide 
• 124-63-0 methanesulfonyl chloride 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 34126-16-4 4-bromo-3,5-dihydroxy-benzoic acid methyl ester 

Downstream Products

• 50874-18-5 5,3',5'-trimethoxy-3,4'-oxy-di-benzoic acid dimethyl ester 
• 866821-31-0 methyl 3,5-dimethoxy-4-(prop-1-en-2-yl)benzoate 
• 1041205-11-1 methyl 4-[1-(ethoxy)ethenyl]-3,5-dimethoxybenzoate 
• 1262310-89-3 C₁₂H₁₄O₄ 
• 55687-68-8 methyl-4-cyano-3,5-dimethoxybenzoate 
• 1432496-20-2 (4-(aminomethyl)-3,5-dimethoxyphenyl)methanol 
• 1550060-43-9 4-bromo-3,5-dimethoxyphenyl acetic acid 
• 1550061-20-5 methyl 2-(4-bromo-3,5-dimethoxyphenyl)acetate 
• 1550060-63-3 3-bromo-2,4-dimethoxy-6-(2-methoxy-2-oxoethyl)benzoic acid 
• 1550060-75-7 3-bromo-6-(carboxymethyl)-2,4-dimethoxybenzoic acid (4-bromo-3,5-dimethoxyhomophthalic acid) 
• 1550060-81-5 7-bromo-6,8-dimethoxy-3-(4-methoxyphenethyl)isocoumarin 
• 1550060-88-2 (E)-7-bromo-6,8-dimethoxy-3-(4-methoxystyryl)isocoumarin 
• 1550060-94-0 (E)-7-(3,7-dimethylocta-2,6-dien-1-yl)-6,8-dimethoxy-3-(4-methoxyphenethyl)-1H-isochromen-1-one 
• 1550060-99-5 7-((E)-3,7-dimethylocta-2,6-dien-1-yl)-6,8-dimethoxy-3-((E)-4-methoxystyryl)-1H-isochromen-1-one 

Relevant academic research and scientific papers

Chain substituted cannabilactones with selectivity for the CB2 cannabinoid receptor

In earlier work, we reported a novel class of CB2 selective ligands namely cannabilactones. These compounds carry a dimethylheptyl substituent at C3, which is typical for synthetic cannabinoids. In the current study with the focus on the pharmacophoric side chain at C3 we explored the effect of replacing the C1′-gem-dimethyl group with the bulkier cyclopentyl ring, and, we also probed the chain's length and terminal carbon substitution with bromo or cyano groups. One of the analogs synthesized namely 6-[1-(1,9-dihydroxy-6-oxo-6H-benzo[c]chromen-3-yl) cyclopentyl] hexanenitrile (AM4346) has very high affinity (Ki = 4.9 nM) for the mouse CB2 receptor (mCB2) and 131-fold selectivity for that target over the rat CB1 (rCB1). The species difference in the affinities of AM4346 between the mouse (m) and the human (h) CB2 receptors is reduced when compared to our first-generation cannabilactones. In the cyclase assay, our lead compound was found to be a highly potent and efficacious hCB2 receptor agonist (EC50 = 3.7 ± 1.5 nM, E(max) = 89%). We have also extended our structure-activity relationship (SAR) studies to include biphenyl synthetic intermediates that mimic the structure of the phytocannabinoid cannabinodiol.

Br...O contacts and π-π Stacking dominate the packing in methyl 4-bromo-3,5-dimethoxybenzoate

The title compound, C10H11BrO4, a useful precursor to pharmaceutically active isocoumarin and isochroman derivatives, crystallizes with two unique molecules in the asymmetric unit. A π-π stacking interaction links the planar molecules in the asymmetric unit. Additional π-π contacts stack pairs of molecules along the c axis. A feature of the crystal packing is the presence of a number of short Br...O contacts. A particularly unusual arrangement involves the formation of dimers, with pairs of Br...O contacts imposing a close Br...Br interaction and generating five-membered rings within an eight-membered ring formed by two Br...O contacts. Only two comparable arrangements have been reported previously. The Br...O contacts combine with weak C - H...O hydrogen bonds to form corrugated sheets of molecules approximately parallel to (001). These sheets are stacked along the c axis by π-π interactions to generate a three-dimensional network.

Synthesis and NMR analysis of a conformationally controlled β-Turn Mimetic Torsion Balance

The molecular torsion balance concept was applied to a new conformationally controlled scaffold and synthesized to accurately evaluate pairwise amino acid interactions in an antiparallel β-sheet motif. The scaffold's core design combines (ortho-tolyl)amide and o,o,o′-trisubstituted biphenyl structural units to provide a geometry better-suited for intramolecular hydrogen bonding. Like the dibenzodiazocine hinge of the traditional torsion balance, the (ortho-tolyl)amide unit offers restricted rotation around an N-aryl bond. The resulting two-state folding model is a powerful template for measuring hydrogen bond stability between two competing sequences. The aim of this study was to improve the alignment between the amino acid sequences attached to the upper and lower aromatic rings in order to promote hydrogen bond formation at the correct distance and antiparallel orientation. Bromine substituents were introduced ortho to the upper side chains and compared to a control to test our hypothesis. Hydrogen bond formation has been identified between the NH amide proton of the upper side chain (proton donor) and glycine acetamide of the lower side chain (proton acceptor).

Xylochemical synthesis and biological evaluation of shancigusin c and bletistrin g

The biological activities of shancigusin C (1) and bletistrin G (2), natural products isolated from orchids, are reported along with their first total syntheses. The total synthesis of shancigusin C (1) was conducted by employing the Perkin reaction to forge the central stilbene core, whereas the synthesis of bletistrin G (2) was achieved by the Wittig olefination followed by several regiose-lective aromatic substitution reactions. Both syntheses were completed by applying only renewable starting materials according to the principles of xylochemistry. The cytotoxic properties of shancigusin C (1) and bletistrin G (2) against tumor cells suggest suitability as a starting point for further structural variation.

SUBSTITUTED TRICYCLIC COMPOUNDS

Disclosed are compounds of the general formula (I), its tautomeric form, its stereoisomer, its pharmaceutically acceptable salt, its polymorph, or solvate thereof, Formula (I) wherein, ring A, R1 to R5, X, Y, m, and n are as defined herein, for use as SOS1 inhibitors in the treatment of proliferative, infectious and RASopathy diseases or disorders. Also disclosed are methods of synthesizing the compound of formula I, pharmaceutical compositions containing the compound of formula I, method of treatment of proliferative, infectious and RASopathy diseases or disorder, for example, a cancer, by administering the said compound and combinations of the compound of formula I with other active ingredients.

Btk INHIBITORS WITH IMPROVED DUAL SELECTIVITY

Disclosed herein is a tri-substituted phenyl Btk inhibitors with improved dual selectivity, a method and a composition for inhibiting Btk and treating disease associated with undesirable Btk activity (Btk-related diseases).

INTEGRIN ANTAGONISTS

The present disclosure provides therapeutic agents including those of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such therapeutic agents. Methods of using the therapeutic agents are also provided.

TERTIARY AMIDES AND METHOD OF USE

Compunds of Formula (I) and pharmaceutically acceptable salts thereof, wherein G1, G2, G3, L1, L2, and L3 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by the modulation of lysophosphatidic acid receptor 1. Methods for making the compounds are described. Also described are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

Extended structure-activity study of thienopyrimidine-based EGFR inhibitors with evaluation of drug-like properties

Thieno[2,3-d]pyrimidines are attractive derivatives for cancer treatment, among others through regulation of the epidermal growth factor receptor tyrosine kinase (EGFR-TK). In an extended SAR study, 44 new compounds of this class have been evaluated as inhibitors, while simultaneously focussing on ADME properties. Through the application of bioisosters, hybrid structures, solubilizing tails, and a combination approach several successful alterations in terms of activity and physiochemical properties were accomplished. Compounds based on benzylamines were found superior to aniline hybrid structures with respect to activity and ADME profile. Exploration of the former class revealed meta-and para amides as favourable 6-aryl substituents, contributing to an increase in activity and acting as a linker for solubilizing tails. Next, combinations of activity-inducing groups on the same scaffold resulted in new drug candidates. Compounds containing 6-aryls with the (2-(dimethylamino)ethyl)carbamoyl substituent were found equipotent to Erlotinib. Compared to this commercial drug, improved solubility and metabolic stability were observed. However, the thieno[2,3-d]pyrimidines with a solubilizing tail was by Caco-2 experiments found to have permeability issues, making further drug development difficult. Selected compounds were further analysed for toxicity and teratogenicity in zebrafish embryos. Two thienopyrimidines were both found to be less lethal than Erlotinib and to perform as well in terms of teratogenicity. Finally, the most promising thienopyrimidine drug was evaluated in a panel of human cancer cell lines, showing a clear potential for thienopyrimidines as anti-cancer agents.

Radiosynthesis and characterisation of a potent and selective GPR139 agonist radioligand

Compound 1 is a selective and potent agonist of the G protein-coupled receptor GPR139 (EC50 = 39 nM). In this study, we describe the synthesis, radiolabelling and in vitro evaluation of [3H]-1 for the characterisation of GPR139 and its spatial expression in the brain using autoradiography. Two different synthesis routes for the radiolabelling of 1 based on a reductive debromination strategy were investigated using deuterium (D2, g). The route based on reductive debromination of the bromonaphthyl precursor 5 proved superior over arylbromide 4 and was employed for the radiolabelling experiments. Reductive debromination of precursor 5 was accomplished using 3H2, Pd/C and triethylamine in DMF at ambient temperature to give target molecule [3H]-1 with a specific activity of 19.3 Ci mmol-1 and a radiochemical purity of ≥95%. By application of autoradiography and binding studies, it was not possible to discriminate [3H]-1 binding to wildtype mice brains from GPR139 knockout mice brains and total binding from non-specific binding in CHO-k1 cells stably expressing human GPR139 receptor. Based on these experiments we conclude that [3H]-1 is not a suitable radioligand for the characterisation of GPR139.