304854-54-4

Usage

General Description

2-Amino-5-bromo-N-methoxy-N-methylbenzamide is a chemical compound with the molecular formula C9H10BrN2O2. It is a derivative of benzamide and contains an amino group, a bromine atom, and a methoxy group attached to the benzene ring. 2-Amino-5-bromo-N-methoxy-N-methylbenzamide has potential pharmaceutical applications, particularly in the development of new drugs. Its structure and properties make it a valuable building block in the synthesis of other organic compounds, and it may also exhibit biological activity that could be useful in medical research. The specific properties and potential uses of 2-Amino-5-bromo-N-methoxy-N-methylbenzamide make it a compound of interest for further study and application in the field of chemistry and pharmaceutical science.

Upstream product

• 4692-98-2 5-bromoisatoic anhydride 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 74189-16-5 2-amino-5-bromobenzoic acid hydrochloride 

Downstream Products

• 39859-36-4 2-amino-5-bromobenzophenone 
• 65247-25-8 (2-amino-5-bromo-phenyl)-(3-chloro-phenyl)-methanone 
• 929489-85-0 C₁₄H₁₂BrNO 
• 1118761-76-4 C₁₇H₁₂BrNO 
• 1118761-75-3 (2-amino-5-bromophenyl)(3-chloro-2-methylphenyl)methanone 
• 1262394-32-0 6-tert-butoxy-4-(4-methylphenyl)-2-(2-methylpropyl)quinoline-3-carbonitrile 
• 660452-07-3 tert-butyl {[6-(3-hydroxypropyl)-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-3-yl]methyl}carbamate 
• 660451-99-0 tert-butyl {[6-(5-cyanopent-1-yn-1-yl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate 
• 1262394-33-1 ethyl 3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]propanoate 
• 660451-15-0 3-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]propanoic acid 
• 660452-09-5 4-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]butanoic acid 
• 1262394-34-2 ethyl 5-[3-cyano-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]pentanoate 
• 660451-87-6 ethyl 5-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]pentanoate 
• 660451-88-7 5-[3-{[(tert-butoxycarbonyl)amino]methyl}-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl]pentanoic acid 

Relevant academic research and scientific papers

TEAD INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization

A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.

Synthesis of Flubromazepam Positional Isomers for Forensic Analysis

Designer benzodiazepines have recently appeared in many forensic cases as legal alternatives to federally scheduled drugs such as diazepam (Valium) and alprazolam (Xanax). Though current forensic instrumental techniques are often sufficient for identifying novel psychoactive substances, they may not readily differentiate between potential positional isomers. Additionally, characterization data for positional isomers of known designer benzodiazepines are widely nonexistent. In this study, flubromazepam, a recognized designer benzodiazepine since 2012, was targeted for synthesis and characterization due to its potential for federal scheduling and current legal status within the United States. A practical synthetic method was developed to prepare purified reference materials for each positional isomer of flubromazepam in which the positions of the bromine and fluorine substituents were varied. Possible isomers (9 of the 12) were successfully prepared and used for further analysis.

Palladium-Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho-Iodo-Tethered Methylenecyclopropanes (MCPs) Using N-Formylsaccharin as CO Source

A palladium-catalyzed reductive and carbonylative cyclization of ortho-iodo-tethered methylenecyclopropanes (MCPs) using N-formylsaccharin as CO source has been developed, affording the desired indanone derivatives in moderate to good yields with high regio- and stereoselectivity and good functional group compatibility.

Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles

An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.

Discovery of a 3-pyridylacetic acid derivative (TAK-100as a potent, selective and orally active dipeptidyl peptidase IV (DPP-4) inhibitor

Inhibition of dipeptidyl peptidase IV (DPP-4is an exciting new approach for the treatment of diabetes. To date there has been no DPP-4 chemotype possessing a carboxy group that has progressed into clinical trials. Originating from the discovery of the str

Discovery of potent, selective, and orally bioavailable quinoline-based dipeptidyl peptidase IV inhibitors targeting Lys554

Dipeptidyl peptidase IV (DPP-4) inhibition is a validated therapeutic option for type 2 diabetes, exhibiting multiple antidiabetic effects with little or no risk of hypoglycemia. In our studies involving non-covalent DPP-4 inhibitors, a novel series of quinoline-based inhibitors were designed based on the co-crystal structure of isoquinolone 2 in complex with DPP-4 to target the side chain of Lys554. Synthesis and evaluation of designed compounds revealed 1-[3-(aminomethyl)-4-(4-methylphenyl)-2-(2-methylpropyl)quinolin-6-yl] piperazine-2,5-dione (1) as a potent, selective, and orally active DPP-4 inhibitor (IC50 = 1.3 nM) with long-lasting ex vivo activity in dogs and excellent antihyperglycemic effects in rats. A docking study of compound 1 revealed a hydrogen-bonding interaction with the side chain of Lys554, suggesting this residue as a potential target site useful for enhancing DPP-4 inhibition.

Second generation analogues of the cancer drug clinical candidate tipifarnib for anti-chagas disease drug discovery

We previously reported that the cancer drug clinical candidate tipifarnib kills the causative agent of Chagas disease, Trypanosoma cruzi, by blocking ergosterol biosynthesis at the level of inhibition of lanosterol 14α-demethylase. Tipifarnib is an inhibitor of human protein farnesyltransferase. We synthesized tipifarnib analogues that no longer bind to protein farnesyltransferase and display increased potency for killing parasites. This was achieved in a structure-guided fashion by changing the substituents attached to the phenyl group at the 4-position of the quinoline ring of tipifarnib and by replacing the amino group by OMe. Several compounds that kill Trypanosoma cruzi at subnanomolar concentrations and are devoid of protein farnesyltransferase inhibition were discovered. The compounds are shown to be advantageous over other lanosterol 14α-demethylase inhibitors in that they show only modest potency for inhibition of human cytochrome P450 (3A4). Since tipifarnib displays high oral bioavailability and acceptable pharmacokinetic properties, the newly discovered tipifarnib analogues are ideal leads for the development of drugs to treat Chagas disease.

Rational modification of a candidate cancer drug for use against chagas disease

Chagas disease is one of the major neglected diseases of the world. Existing drug therapies are limited, ineffective, and highly toxic. We describe a novel strategy of drug discovery of adapting an existing clinical compound with excellent pharmaceutical properties to target a pathogenic organism. The protein farnesyltransferase (PFT) inhibitor tipifarnib, now in phase III anticancer clinical trials, was previously found to kill Trypanosoma cruzi by blocking sterol 14a-demethylase (14DM). We rationally developed tipifarnib analogues that display reduced affinity for human PFT to reduce toxicity while increasing affinity for parasite 14DM. The lead compound has picomolar activity against cultured T. cruzi and is efficacious in a mouse model of acute Chagas disease.

Quinazoline derivatives, process for their preparation, their use as antimitotics and pharmaceutical compositions comprising said derivatives

The invention relates to quinazoline derivatives of formula (I) in which R1, X and A have the meanings as indicated, or to a pharmaceutically acceptable salt thereof, e.g. Such compounds are useful as modulators, in particular inhibitors, of th