118652-88-3

Basic information

• Product Name: 3-BROMO-4-PIPERIDINONE HYDROBROMIDE
• Synonyms: 3-BROMO-4-PIPERIDINONE HYDROBROMIDE;3-Bromopiperidin-4-one hydrobromide
• CAS NO: 118652-88-3
• Molecular Formula: C5H9Br2NO
• Molecular Weight: 258.94
• Mol File: 118652-88-3.mol

Chemical Properties

• Melting Point: 200-201 °C
• Boiling Point: 232.8 °C at 760 mmHg
• Flash Point: 94.6 °C
• Appearance: /
• Vapor Pressure: 0.0578mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-BROMO-4-PIPERIDINONE HYDROBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-PIPERIDINONE HYDROBROMIDE(118652-88-3)
• EPA Substance Registry System: 3-BROMO-4-PIPERIDINONE HYDROBROMIDE(118652-88-3)

Safety Data

• Hazardous Substances Data: 118652-88-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-4-piperidinone hydrobromide is used as a key intermediate in the synthesis of antiviral and antibacterial medications. Its reactivity and stability contribute to the development of effective treatments for various viral and bacterial infections.
Used in Chemical Industry:
In the chemical industry, 3-Bromo-4-piperidinone hydrobromide is utilized as a versatile intermediate for the production of a wide range of organic chemicals. Its unique properties allow for the creation of various chemical compounds with diverse applications.
Used in Agricultural Chemical Production:
3-Bromo-4-piperidinone hydrobromide is also employed in the production of agricultural chemicals. Its role as a building block aids in the development of products that can enhance crop protection and improve overall agricultural yields.

InChI:InChI=1/C5H8BrNO.BrH/c6-4-3-7-2-1-5(4)8;/h4,7H,1-3H2;1H

Upstream product

• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 41979-39-9 4-piperidone hydrochloride 
• 73390-11-1 4-piperidinone monohydrate 
• 41661-47-6 piperidin-4-one 
• 676618-22-7 Butyl 4-oxo-piperidine-1-carboxylate 

Downstream Products

• 1004764-03-7 3-bromo-1-(trifluoroacetyl)piperidin-4-one 
• 192869-83-3 2-Methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine hydrochloride 
• 188869-05-8 tert-butyl 3-bromo-4-oxo-piperidine-1-carboxylate 
• 365996-05-0 tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate 
• 1440954-95-9 2-phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester 
• 97817-47-5 N-[1-(2-Guanidino-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)-1-methylsulfanyl-meth-(Z)-ylidene]-4-methyl-benzenesulfonamide 

Relevant articles and documents

Small-molecule activity-based probe for monitoring ubiquitin C?terminal hydrolase L1 (UchL1) activity in live cells and zebrafish embryos

Many reagents have emerged to study the function of specific enzymes in vitro. On the other hand, target specific reagents are scarce or need improvement, allowing investigations of the function of individual enzymes in their native cellular context. Here we report the development of a target-selective fluorescent small-molecule activity-based DUB probe that is active in live cells and an in vivo animal model. The probe labels active ubiquitin carboxy-terminal hydrolase L1 (UCHL1), also known as neuron-specific protein PGP9.5 (PGP9.5) and Parkinson disease 5 (PARK5), a DUB active in neurons that constitutes 1 to 2% of the total brain protein. UCHL1 variants have been linked with neurodegenerative disorders Parkinson’s and Alzheimer’s diseases. In addition, high levels of UCHL1 also correlate often with cancer and especially metastasis. The function of UCHL1 activity or its role in cancer and neurodegenerative disease is poorly understood and few UCHL1-specific activity tools exist. We show that the reagents reported here are specific to UCHL1 over all other DUBs detectable by competitive activity-based protein profiling and by mass spectrometry. Our cell-penetrable probe, which contains a cyanimide reactive moiety, binds to the active-site cysteine residue of UCHL1 in an activity-dependent manner. Its use is demonstrated by the fluorescent labeling of active UCHL1 both in vitro and in live cells. We furthermore show that this probe can selectively and spatiotemporally report UCHL1 activity during the development of zebrafish embryos. Our results indicate that our probe has potential applications as a diagnostic tool for diseases with perturbed UCHL1 activity.

NOVEL COMPOUNDS

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1). The invention further relates to the use of DUB inhibitors in the treatment of cancer and other indications. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R8 are as defined herein.

NOVEL COMPOUNDS

This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, X, R1, R2, R3 have meanings given in the description.

1,2,4 -TRIAZOLES AS ALLOSTERIC MODULATORS OF MGLU5 RECEPTOR ACTIVITY FOR THE TREATMENT OF SCHIZOPHRENIA OF DEMENTIA

This invention relates to compounds of formula (I) their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, X, R1, R2, R3 have meanings given in the description.

NOVEL COMPOUNDS

This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. A, B, X, R1, R2, R3 have meanings given in the description.

COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF

Provided herein are compounds and methods of synthesis thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, psychiatric disorders, neuromuscular disorders, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds provided herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

Design, synthesis, and structure-activity relationships of novel bicyclic azole-amines as negative allosteric modulators of metabotropic glutamate receptor 5

A novel series of diaryl bicyclic azole-amines that are potent selective negative modulators of metabotropic glutamate receptor 5 (mGluR5) were identified through rational design. An initial hit compound 5a of modest potency (IC50 = 1.2 μM) was synthesized. Evaluation of structure-activity relationships (SAR) on the left-hand side of the molecule revealed a preference for a 2-substituted pyridine group linked directly to the central heterocycle. Variation of the central azolo-amine portion of the molecule revealed a preference for the [4,5-c]-oxazoloazepine scaffold, while right-hand side variants showed a preference for ortho- and meta-substituted benzene rings linked directly to the tertiary amine of the saturated heterocycle. These iterations led to the synthesis of 29b, a potent (IC50 = 16 nM) and selective negative modulator that showed good brain penetrance, high receptor occupancy, and a duration of action greater than 1 h in rat when administered intraperitoneally. Formal PK studies in rat and Rhesus monkey revealed a short half-life that was attributable to high first-pass clearance.

Pyrimidine derivatives and methods of making and using these derivatives

This invention discloses compounds, and pharmaceutically acceptable salts thereof, useful in therapeutically and/or prophylactically treating patients with an illness. Such illnesses include cancer, and secondary infections caused by Pneumocystis carinii and Toxoplasmosis gondii in immunocompromised patients. The compounds themselves, methods of making these compounds, and methods of using these compounds are all disclosed.

Synthesis and biological activities of tricyclic conformationally restricted tetrahydropyrido annulated furo[2,3-d]pyrimidines as inhibitors of dihydrofolate reductases

The synthesis of seven 2,4-diamino-5,6,7,8-tetrahydro-7-substituted pyrido[4',3':4,5]furo[2,3-d]pyrimidines 1-6 are reported as nonclassical antifolate inhibitors of dihydrofolate reductase (DHFR) and compound 7 as a classical antifolate inhibitor of tumor cells in culture. The compounds were designed as conformationally restricted analogues of trimetrexate. The synthesis was accomplished from the cyclocondensation of 3-bromo-4-piperidone with 2,4-diamino-6-hydroxypyrimidine to afford regiospecifically 2,4-diamino- 5,6,7,8-tetrahydropyrido-[4',3':4,5]furo[2,3-d]pyrimidine-7-hydrobromide (16). This in turn was alkylated with the appropriate benzyl halide to afford the target compounds 1-6. The classical antifolate 7 utilized 4- (chloromethyl)benzoyl-L-glutamic acid diethyl ester (17) instead of the benzyl halide for alkylation, followed by saponification to afford 7. Compounds 1-6 showed moderate inhibitory potency against DHFR from Pneumocystis carinii, Toxoplasma gondii, Mycobacterium avium, and rat liver. The classical analogue 7 was 88-fold more potent against M. avium DHFR than against rat liver DHFR. The classical analogue was also inhibitory against the growth of tumor cells, CCRF-CEM, and FaDu, in culture.