6943-73-3

Usage

Uses

Used in Pharmaceutical Research and Development:
N-(3-bromo-4-methoxyphenyl)Acetamide is employed as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure, including the bromo and methoxy substituents on the phenyl ring, contributes to its potential as a precursor in the creation of new drugs with specific therapeutic targets.
Used in Drug Discovery:
In the drug discovery process, N-(3-bromo-4-methoxyphenyl)Acetamide is used as a lead compound for the development of new medications. Its structural features allow for modifications and optimization to enhance its biological activity, potentially leading to the discovery of effective treatments for various diseases.
Used in Medicinal Chemistry:
N-(3-bromo-4-methoxyphenyl)Acetamide serves as a valuable tool in medicinal chemistry for the study of structure-activity relationships (SAR). By examining the effects of its structural components on biological activity, researchers can gain insights into the design of more potent and selective drug candidates.
Used in Biological Assays and Screening:
N-(3-bromo-4-methoxyphenyl)Acetamide is utilized in biological assays and high-throughput screening processes to identify its potential anti-inflammatory, analgesic, or other biological activities. Such assays are crucial for evaluating the compound's efficacy and safety before it can be considered for further development as a therapeutic agent.
Used in Chemical Synthesis Education:
N-(3-bromo-4-methoxyphenyl)Acetamide can also be used as an educational tool in teaching chemical synthesis and the principles of medicinal chemistry, providing students with hands-on experience in the synthesis of complex organic molecules and understanding their potential applications in the pharmaceutical industry.

InChI:InChI=1/C9H10BrNO2/c1-6(12)11-7-3-4-9(13-2)8(10)5-7/h3-5H,1-2H3,(H,11,12)

Upstream product

• 51-66-1 4-methoxyacetanilide 
• 5197-28-4 2-bromo-4-nitroanisole 
• 7439-89-6 iron 
• 6329-78-8 N-(3-bromo-4-hydroxyphenyl)acetamide 
• 74-88-4 methyl iodide 
• 19056-41-8 3-bromo-p-anisidine 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 7357-66-6 N-(5-bromo-4-methoxy-2-nitrophenyl)acetamide 
• 108447-01-4 4-bromo-5-methoxy-1,2-phenylenediamine 
• 6943-69-7 5-bromo-4-methoxy-2-nitro-phenylamine 
• 5347-15-9 5-bromo-6-methoxy-8-nitroquinoline 
• 63460-36-6 6-methoxy-5-phenoxy-[8]quinolylamine 
• 61895-55-4 6-methoxy-5-(4-methoxy-phenoxy)-[8]quinolylamine 
• 63505-75-9 6-methoxy-8-nitro-5-phenoxy-quinoline 
• 5452-59-5 6-methoxy-5-(4-methoxy-phenoxy)-8-nitro-quinoline 
• 19056-41-8 3-bromo-p-anisidine 
• 92-52-4 biphenyl 
• 74447-73-7 3-bromo-4-methoxybiphenyl 
• 888738-40-7 methyl (E)-3-(3-bromo-4-methoxyphenyl)acrylate 
• 98081-56-2 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole 

Relevant academic research and scientific papers

SUBSTITUTED ISOXAZOLOPYRIDAZINONES AND ISOTHIAZOLOPYRIDAZINONES AND METHODS OF USE

Compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1, R2 and R3 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by positive allosteric modulation of the γ-aminobutyric acid B (GABA-B) receptor. 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.

Regioselective and efficient bromination of anilides on water using HBr and Selectfluor

A metal-, additive-, and Br2-free highly regioselective bromination of anilides using HBr and Selectfluor is presented. This reaction proceeded under mild conditions with high efficiency and good functional group tolerance, and water served as the solvent. In general, with substrates bearing no para-substituent, para-mono-bromination occurred exclusively, while ortho-mono-brominated anilides were the only products when para-positions were blocked. The incorporation of a stronger orienting group might result in a reversed regioselectivity, and the reaction was sensitive to steric hindrance.

Functionalized alkoxy arene diazonium salts from paracetamol

Arene diazonium tetrafluoroborates can be synthesized from aromatic acetamides via a sequence of deacetylation, diazotation and precipitation, induced by anion exchange. The reaction is conducted as a convenient one-flask transformation with consecutive addition of the appropriate reagents. Exchange of solvents or removal of byproducts prior to isolation of the product is not required. The arene diazonium salts are isolated from the reaction mixture by simple filtration. Two complementary protocols are presented, and the utility of the reaction is exemplified for a synthesis of the diarylheptanoid natural product de-O-methyl centrolobine.

ANTIBACTERIAL CONDENSED THIAZOLES

Compound of formula (I) have antibacterial activity: wherein: m is 0 or 1; Q is hydrogen or cyclopropyl; AIk - is an optionally substituted, divalent C1-C6 alkylene, alkenylene or alkynylene radical which may contain an ether (-0-), thioether (-S-) or amino (-NR)- link, wherein R is hydrogen, -CN or C1-C3 alky!; X is -C(=O)NR6-, or -C(=O)O- wherein R6 is hydrogen, optionally substituted C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl; Z1 is -N= or -CH= Z2 is -N= or -C(R1)=; R1 is hydrogen, methyl, ethyl, ethenyl, ethynyl, methoxy, mercapto, mercaptomethyl halo, fully or partially fluorinated (C1-C2)alkyl, (C1-C2JaIkOXy or (C1-C2)alkylthio, nitro, or nitrile (-CN); R2 is a group Q1 -[Alk1]q-Q2 -, wherein q is 0 or 1; AIkl is an optionally substituted, divalent, straight chain or branched C1-C6 alkylene, or C2-C6 alkenylene or C2-C6 alkynylene radical which may contain or terminate in an ether (-O-), thioether (-S-) or amino (-NR)- link; Q2 is an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 5 or 6 ring atoms or an optionally substituted divalent bicyclic carbocyclic or heterocyclic radical having 9 or 10 ring atoms; Q1 is hydrogen, an optional substituent or an optionally substituted carbocyclic or heterocyclic radical having 3-7 ring atoms

Investigation of novel 7,8-disubstituted-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-ones as potent Chk1 inhibitors

The synthesis and structure-activity relationships (SAR) of Chk1 inhibitors based on a 5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one core are described. Specifically, an exploration of the 7 and 8 positions on this previously disclosed core afforded compounds with improved enzymatic and cellular potency.

Synthesis and anti-breast cancer activities of substituted quinolines

Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy)quinoline (14). The amino function of 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline, prepared from 14, was connected to various side chains via alkylation with N-(3-iodopropyl)phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC50 value of 6-methoxy-8-[(2-furanylmethyl)amino]-4-methyl-5-(3-trifluoromethylphenyl oxy)quinoline is 16 ± 3 nM, the lowest IC50 out of all the quinolines tested. IC50 values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing.

COMPOUNDS AFFECTING GAP JUNCTION ACTIVITY

ThThis invention relates to novel quinoline compounds which affect gap junction activity. Also provided are methods of using such compounds and compositions containing the compounds to treat gap junction disorders.

HETEROCYCLIC KINASE INHIBITORS

Compounds having the formula (I) are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

1-substituted phenyl-1-(1h-imidazol-4-yl) alcohols, process for producing the same and use thereof

To provide a composition having a steroid C17,20-lyase inhibitory activity and useful as an agent for the prophylaxis or treatment of prostatism and tumors such as breast cancer. A compound represented by the formula: wherein R is a hydrogen atom or a protecting group, R1is a lower alkyl group or a cyclic hydrocarbon group, R2is an aromatic hydrocarbon group optionally having substituents or an aromatic heterocyclic group optionally having substituents, R3is a hydrocarbon group optionally having substituents, a hydroxyl group optionally having substituents, a thiol group optionally having substituents, an amino group optionally having substituents, an acyl group or a halogen atom, and n is an integer of 0 to 4, and a salt thereof have a steroid C17,20-lyase inhibitory activity, and are useful as an agent for the pophylaxis or treatment of prostatism and tumors such as beast cancer and the like.

Synthesis, antimalarial activity, and molecular modeling of tebuquine analogues

Tebuquine (5) is a 4-aminoquinoline that is significantly more active than amodiaquine (2) and chloroquine (1) both in vitro and in vive. We have developed a novel more efficient synthetic route to tebuquine analogues which involves the use of a palladium-catalyzed Suzuki reaction to introduce the 4- chlorophenyl moiety into the 4-hydrexyaniline side chain. Using similar methodology, novel synthetic routes to fluorinated (7a,b) and a dehydroxylated (7c) analogue of tebuquine have also been developed. The novel analogues were subjected to testing against the chloroquine sensitive HB3 strain and the chloroquine resistant K1 strain of Plasmodium falciparum. Tebuquine was the most active compound tested against both strains of Plasmodia. Replacement of the 4-hydroxy function with either fluorine or hydrogen led to a decrease in antimalarial activity. Molecular modeling of the tebuquine analogues alongside amodiaquine and chloroquine reveals that the inter-nitrogen separation in this class of drugs ranges between 9.36 and 9.86 ? in their isolated diprotonated form and between 7.52 and 10.21 ? in the heme-drug complex. Further modeling studies on the interaction of 4- aminoquinolines with the proposed cellular receptor heme revealed favorable interaction energies for chloroquine, amodiaquine, and tebuquine analogues. Tebuquine, the most potent antimalarial in the series, had the most favorable interaction energy calculated in both the in vacuo and solvent-based simulation studies. Although fluorotebuquine (7a) had a similar interaction energy to tebuquine, this compound had significantly reduced potency when compared with (5). This disparity is possibly the result of the reduced cellular accumulation (CAR) of fluorotebuquine when compared with tebuquine within the parasite. Measurement of the cellular accumulation of the tebuquine analogues and seven related 4-aminoquinolines shows a significant relationship (r = 0.98) between the CAR of 4-aminoquinoline drugs and the reciprocal of drug IC50.