20772-12-7

Usage

Uses

1-bromo-3-phenylpropan-2-one is used as a synthetic intermediate for the production of various pharmaceutical agents. Its application is primarily in the synthesis of tyrosine kinase inhibitors and antiangiogenic agents, which are important in the treatment of cancer.
Used in Pharmaceutical Industry:
1-bromo-3-phenylpropan-2-one is used as a key intermediate in the synthesis of tyrosine kinase inhibitors for the Pharmaceutical Industry. These inhibitors play a crucial role in blocking the activity of tyrosine kinases, which are enzymes often overexpressed in cancer cells, thereby contributing to the uncontrolled growth and proliferation of these cells.
Additionally, 1-bromo-3-phenylpropan-2-one is used as a precursor in the development of antiangiogenic agents within the Pharmaceutical Industry. Antiangiogenic agents work by inhibiting the formation of new blood vessels, which is a process that cancer cells exploit to grow and spread. By disrupting this process, these agents can limit the growth and metastasis of tumors.

InChI:InChI=1/C9H9BrO/c10-7-9(11)6-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 28988-98-9 1-bromo-3-phenylpropan-2-ol 
• 186581-53-3 diazomethane 
• 103-80-0 phenylacetyl chloride 
• 95547-16-3 1-Phenyl-3-(trimethylsilyl)propan-2-one 
• 103-79-7 1-phenyl-acetone 
• 1589-82-8 phenylmagnesium bromide 
• 598-21-0 2-Bromoacetyl bromide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 103-82-2 phenylacetic acid 
• 591-50-4 iodobenzene 
• 24193-22-4 (+/-)-(2S,3R)-2-(bromomethyl)-3-phenyloxirane 
• 300-57-2 allylbenzene 
• 1555-80-2 phenylacetic anhydride 
• 4250-02-6 1-diazo-3-phenyl-2-propanone 

Downstream Products

• 23022-83-5 1-bromo-1-phenyl-2-propanone 
• 237384-72-4 Methyl 5-methylthio-4-[4-benzyl(1,3-thiazol-2-yl)]thiophene-2-carboxylate 
• 651358-43-9 2-amino-4-oxo-6-benzyl-3,7-dihydropyrrolo[2,3-d]pyrimidine 
• 851460-94-1 dithiocarbonic acid O-ethyl ester S-(2-oxo-3-phenylpropyl) ester 
• 144449-39-8 3-benzamidomethyl-2-benzyl-6-chloroimidazo<1,2-b>pyridazine 
• 144449-27-4 2-benzyl-3-dimethylaminomethyl-6-phenylthioimidazo<1,2-b>pyridazine 
• 144449-26-3 2-benzyl-6-(4'-chlorophenoxy)-3-dimethylaminomethylimidazo<1,2-b>pyridazine 
• 144449-25-2 2-benzyl-3-dimethylaminomethyl-6-(4'-methoxyphenoxy)imidazo<1,2-b>pyridazine 
• 144449-23-0 2-benzyl-3-dimethylaminomethyl-6-(4'-methoxybenzylthio)imidazo<1,2-b>pyridazine 
• 144449-22-9 2-benzyl-3-dimethylaminomethyl-6-(3'-methoxybenzylthio)imidazo<1,2-b>pyridazine 
• 144449-24-1 2-benzyl-3-dimethylaminomethyl-6-(2'-methoxyphenoxy)imidazo<1,2-b>pyridazine 
• 144449-21-8 2-benzyl-3-dimethylaminomethyl-6-(2'-methoxybenzylthio)imidazo<1,2-b>pyridazine 
• 76467-35-1 hydrobromide salts of 1-(methylamino)-3-phenylacetone 
• 301220-64-4 4-(5-benzyl-thiazol-2-yl)-1-t-butyloxycarbonyl-piperidine 

Relevant academic research and scientific papers

Regiospecific synthesis of unsymmetrical α-bromoketones

A convenient regiospecific preparation of unsymmetrical α-bromoketones, commencing from Meldrum's acid, has been developed. This procedure allows for preparation of α-bromoketones which are unobtainable in a pure state by other bromination methods and is

PYRROLO [2,3-B]PYRIDINE-3-CARBOXAMIDE COMPOSITIONS AND METHODS FOR AMELIORATING HEARING LOSS

N-(3-Substituted thiazol-2(3H)-ylidene)-1H-pyrrolo[2,3-b]pyridine-3-carboxamides and N-(3-substituted oxazol-2(3H)-ylidene)-1H-pyrrolo[2,3-b]pyridine-3-carboxamides (I) and (II) are disclosed. The compounds activate Yap and inhibit Lats kinases. They are therefore useful for treating hearing loss.

Synthesis of 4-(3-oxo-3-phenylpropyl)morpholin-4-ium chloride analogues and their inhibitory activities of nitric oxide production in lipopolysaccharide-induced BV2 cells

Based on our previous report that 3-morpholino-1-phenylpropan-1-one 2, one of the fluoxetine's simplified morpholino analogue, inhibited nitric oxide (NO) production, in this paper, various substituted benzene analogues with morpholine hydrochloride of 2 were synthesized and their inhibitory effects on NO production in lipopolysaccharide (LPS)-induced BV2 cells were tested. Among the synthesized compounds, 2-trifluoromethyl analogue 16n (IC50 = 8.6 μM) showed a significantly higher inhibitory activity than that of the parent compound 2a (IC50 > 50 μM) and suppressed NO production dose-dependently without cytotoxicity. Compound 16n also inhibited iNOS expression in LPS-induced BV2 cells at 2, 10 and 20 μM concentrations. These results suggest that compound 16n inhibited NO production by suppressing the expression of iNOS and can be used as a lead structure for developing new inhibitor of NO production.

POLYCYCLIC COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF RAPIDLY ACCELERATED FIBROSARCOMA POLYPEPTIDES

The present disclosure relates to bifunctional compounds, ULM— L—PTM, which find utility as modulators of Rapidly Accelerated Fibrosarcoma (RAF, such as c-RAF, A- RAF and/or B-RAF; the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein RAF, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein, or the constitutive activation of the target protein, are treated or prevented with compounds and compositions of the present disclosure.

Design, synthesis, SAR and biological investigation of 3-(carboxymethyl)rhodanine and aminothiazole inhibitors of Mycobacterium tuberculosis Zmp1

Sixteen 3-(carboxymethyl)rhodanines, and twelve aminothiazoles as rhodanine-mimetics were designed, synthesized and tested as inhibitors of the Zmp1 enzyme from Mycobacterium tuberculosis (Mtb). Almost all rhodanines (5a–d, 5f–n, and 7a–b) exhibited Zmp1 inhibition with IC50 values in the range 1.3–43.9 μM, whereas only aminothiazoles 12b and 12d proved active with IC50 values of 41.3 and 35.7 μM, respectively. Structure-activity relationships (SAR) were coupled with molecular modeling studies to highlight structural determinants for Zmp1 inhibition. Moreover, rhodanines 5a and 5c induced 23.4 and 53.8% of Mtb growth inhibition in THP-1 infected cells, respectively, at the non-toxic concentration of 10 μg/ml. This work represents a step forward in targeting Zmp1 by small molecules.

FUSED MORPHOLINOPYRIMIDINES AND METHODS OF USE THEREOF

The present disclosure relates to Fused Morpholinopyrimidines, pharmaceutical compositions comprising an effective amount of a Fused Morpholinopyrimidine and methods for using a Fused Morpholinopyrimidine in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of a Fused Morpholinopyrimidine.

FUSED MORPHOLINOPYRIMIDINES AND METHODS OF USE THEREOF

The present disclosure relates to Fused Morpholinopyrimidines, pharmaceutical compositions comprising an effective amount of a Fused Morpholinopyrimidine and methods for using a Fused Morpholinopyrimidine in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of a Fused Morpholinopyrimidine.

FUSED MORPHOLINOPYRIMIDINES AND METHODS OF USE THEREOF

The present disclosure relates to Fused Morpholinopyrimidines, pharmaceutical compositions comprising an effective amount of a Fused Morpholinopyrimidine and methods for using a Fused Morpholinopyrimidine in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of a Fused Morpholinopyrimidine.

P2X4 RECEPTOR MODULATING COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are P2X4 receptor modulating compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, including but not limited to, chronic pain, neuropathy, inflammatory diseases and central nervous system disorders.

Design, synthesis and evaluation of 2-amino-4-m-bromoanilino-6-arylmethyl- 7H-pyrrolo[2,3-d]pyrimidines as tyrosine kinase inhibitors and antiangiogenic agents

A series of 2-amino-4-m-bromoanilino-6-benzyl pyrrolo[2,3-d]pyrimidines analogues 4-12 were synthesized and evaluated as inhibitors of receptor tyrosine kinases (RTKs). These analogues were synthesized from the appropriate α-bromomethylbenzylketones via cyclocondensation with 2,6-diamino-4- pyrimidone to afford the 2-amino-4-oxo-6-substituted benzyl pyrrolo[2,3-d] pyrimidines. Chlorination at the 4-position followed by displacement with 3-bromoaniline or 3-bromo-N-methylaniline and methylation of the 7-NH afforded the target compounds. Remarkably, dimethylation of both the 4-N and N7 afford whole cell EGFR inhibitors that are more cytotoxic than clinically used erlotinib and mono-methylation at the 4-N or N7 affords more cytotoxic whole cell PDGFR-β inhibitors than clinically used sunitinib. Methylation at either the 4-N or N7 position was detrimental to whole cell VEGFR-2 inhibition. The inhibitory data against the RTKs in this study demonstrates that methylation of the 4-NH and/or the 7-NH influences both the specificity and potency of RTK inhibition.