25503-90-6

Basic information

• Product Name: 1-Acetyl-4-piperidinecarboxylic acid
• Synonyms: 4-Piperidinecarboxylic acid, 1-acetyl-;RARECHEM AL BO 0864;N-ACETYLISONIPECOTIC ACID;TIMTEC-BB SBB000171;BUTTPARK 96\50-12;1-ACETYL-4-PIPERIDINECARBOXYLIC ACID;1-ACETYLISONIPECOTIC ACID;1-ACETYLPIPERIDINE-4-CARBOXYLIC ACID
• CAS NO: 25503-90-6
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19
• EINECS: 247-049-6
• Product Categories: Piperidines, Piperidones, Piperazines;Pyridine series;PiperidineDerivative;API intermediates;Heterocyclic Compounds;Neurochemicals;Carboxylic Acids;Pyrans, Piperidines & Piperazines;Heterocycles;Building Blocks;C8;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 25503-90-6.mol

Chemical Properties

• Melting Point: 180-184 °C(lit.)
• Boiling Point: 301.17°C (rough estimate)
• Flash Point: 180 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.1998 (rough estimate)
• Vapor Pressure: 1.26E-06mmHg at 25°C
• Refractive Index: 1.4750 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 4.35±0.20(Predicted)
• Water Solubility: 50 g/L (20 ºC)
• BRN: 389577
• CAS DataBase Reference: 1-Acetyl-4-piperidinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Acetyl-4-piperidinecarboxylic acid(25503-90-6)
• EPA Substance Registry System: 1-Acetyl-4-piperidinecarboxylic acid(25503-90-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 25503-90-6(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Acetyl-4-piperidinecarboxylic acid is used as a synthetic intermediate for the production of CNS depressants, which are essential in the treatment of various neurological and psychiatric disorders.
2. Used in Chemical Synthesis:
1-Acetyl-4-piperidinecarboxylic acid is used as a reactant for the synthesis of various compounds, including:
a. Triazole derivatives, which have potential applications in the development of new pharmaceuticals and agrochemicals.
b. Antiproliferative agents, which are crucial in the development of cancer treatments.
c. CDK inhibitors, which play a role in regulating cell cycle progression and have potential applications in cancer therapy.
d. CCR5 antagonists, which are used in the treatment of HIV by blocking the entry of the virus into host cells.
e. nhNK1 antagonists, which may have potential applications in the treatment of pain and inflammation.
f. Piperidine derivatives, which are found in various pharmaceuticals and have diverse biological activities.
3. Used in Metabolomics Research:
1-Acetyl-4-piperidinecarboxylic acid is used in metabolite fingerprinting to study the effects of genetic modifications on the metabolism of transgenic Nicotiana tabacum plants, altered by the Escherichia coli glutamate dehydrogenase gene. This application aids in understanding the metabolic changes and potential implications of genetic modifications in plants.

InChI:InChI=1/C8H13NO3/c1-6(10)9-4-2-7(3-5-9)8(11)12/h7H,2-5H2,1H3,(H,11,12)/p-1

Upstream product

• 498-94-2 isonipecotic acid 
• 108-24-7 acetic anhydride 
• 53220-36-3 1-(4-chloro-phenyl)-1-piperidin-4-yl-ethanol 
• 108-10-1 4-methyl-2-pentanone 
• 3874-54-2 4-(4-fluorophenyl)-4-oxo-n-butyl chloride 
• 5984-56-5 piperidine-4-carboxylic acid hydrochloride 
• 75-36-5 acetyl chloride 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 

Downstream Products

• 59084-16-1 1-acetylpiperidine-4-carbonyl chloride 
• 25519-77-1 1-(4-(4-fluorobenzoyl)piperidin-1-yl)ethanone 
• 38081-60-6 phenyl-piperidin-4-yl-methanol 
• 59084-15-0 N-acetyl-4-(p-chlorobenzoyl)piperidine 
• 56346-57-7 (4-fluorophenyl)-piperidin-4-ylmethanone 
• 25519-79-3 1-(4-benzoylpiperidin-1-yl)ethanone 
• 53220-41-0 4-(4-chlorobenzoyl)piperidine 
• 92196-29-7 (1-methylpiperidin-4-yl)(phenyl)methanol 
• 92040-00-1 (1-methylpiperidin-4-yl)(phenyl)methanone 
• 160296-40-2 tert-butyl 1-[4-(4-fluorobenzoyl)piperidin-1-yl]carboxylate 
• 160296-41-3 4-[(4-fluorophenyl)hydroxymethyl]piperidine-1-carboxylic acid tert-butyl ester 
• 193217-39-9 1-(t-butoxycarbonyl)-4-(benzoyl)piperidine 
• 209808-06-0 tert-butyl 4-(4-chlorobenzoyl)piperidine-1-carboxylate 

Relevant articles and documents

Structural and Functional Study of the Klebsiella pneumoniae VapBC Toxin-Antitoxin System, including the Development of an Inhibitor That Activates VapC

Klebsiella pneumoniae is one of the most critical opportunistic pathogens. TA systems are promising drug targets because they are related to the survival of bacterial pathogens. However, structural information on TA systems in K. pneumoniae remains lacking; therefore, it is necessary to explore this information for the development of antibacterial agents. Here, we present the first crystal structure of the VapBC complex from K. pneumoniae at a resolution of 2.00 ?. We determined the toxin inhibitory mechanism of the VapB antitoxin through an Mg2+ switch, in which Mg2+ is displaced by R79 of VapB. This inhibitory mechanism of the active site is a novel finding and the first to be identified in a bacterial TA system. Furthermore, inhibitors, including peptides and small molecules, that activate the VapC toxin were discovered and investigated. These inhibitors can act as antimicrobial agents by disrupting the VapBC complex and activating VapC. Our comprehensive investigation of the K. pneumoniae VapBC system will help elucidate an unsolved conundrum in VapBC systems and develop potential antimicrobial agents.

Synthesis of Novel Aryloxyethylamine Derivatives and Evaluation of Their in Vitro and in Vivo Neuroprotective Activities

A series of aryloxyethylamine derivatives were designed, synthesized and evaluated for their biological activity. Their structures were confirmed by 1H-NMR, 13C-NMR, FT-IR and HR-ESI-MS. The preliminary screening of neuroprotection of compounds in vitro was detected by MTT, and the anti-ischemic activity in vivo was tested using bilateral common carotid artery occlusion in mice. Most of these compounds showed potential neuroprotective effects against the glutamate-induced cell death in differentiated rat pheochromocytoma cells (PC12 cells), especially for (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone, (4-bromophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, (4-chlorophenyl)(1-{2-[(naphthalen-2-yl)oxy]ethyl}piperidin-4-yl)methanone, (4-chlorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone and {1-[2-(4-bromophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone, which exhibited potent protection of PC12 cells at three doses (0.1, 1.0, 10 μM). Compounds (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, (4-fluorophenyl){1-[2-(naphthalen-2-yloxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed the significant prolongation of the survival time of mice subjected to acute cerebral ischemia and decreased the mortality rate at all five doses tested (200, 100, 50, 25, 12.5 mg/kg) and had significant neuroprotective activity. In addition, (4-fluorophenyl){1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}methanone, {1-[2-(4-methoxyphenoxy)ethyl]piperidin-4-yl}(4-methoxyphenyl)methanone and {1-[2-(4-chlorophenoxy)ethyl]piperidin-4-yl}(4-chlorophenyl)methanone possessed outstanding neuroprotection in vitro and in vivo. These compounds can be used as a promising neuroprotective agents for future development of new anti-ischemic stroke agents. Basic structure–activity relationships are also presented.

1-aryloxy ethyl piperidine-4-yl benzophenone derivative as well as preparation method and application thereof

The invention discloses a 1-aryloxy ethyl piperidine-4-yl benzophenone derivative as well as a preparation method and application thereof. The compound is a free alkali or salt with a compound of a formula (I) shown in the specification; the salt is one of hydrochloride, hydrobromide, sulfate, trifluoroacetate, tartrate, lactate or mesylate; in the formula, R1 independently represents H, halogen,alkyl, halogen-substituted alkyl, nitryl, amino, nitrile, hydroxyl, alkoxy, aryl alkoxy, heterocyclic alkoxy, aryl, substituted heterocyclic ring or substituted aryl; and R2 is independently selectedfrom H, halogen, alkyl, halogen substituted alkyl, nitryl, amino, nitrile, hydroxyl, alkoxy, aryl alkoxy, heterocyclic alkoxy, aryl, substituted heterocyclic ring or substituted aryl. The 1-aryloxy ethyl piperidine-4-yl benzophenone derivative is applied to preparation of medicines for treating cerebral arterial thrombosis.

Optimization of a Benzoylpiperidine Class Identifies a Highly Potent and Selective Reversible Monoacylglycerol Lipase (MAGL) Inhibitor

Monoacylglycerol lipase (MAGL) is the enzyme degrading the endocannabinoid 2-arachidonoylglycerol, and it is involved in several physiological and pathological processes. The therapeutic potential of MAGL is linked to several diseases, including cancer. The development of MAGL inhibitors has been greatly limited by the side effects associated with the prolonged MAGL inactivation. Importantly, it could be preferable to use reversible MAGL inhibitors in vivo, but nowadays only few reversible compounds have been developed. In the present study, structural optimization of a previously developed class of MAGL inhibitors led to the identification of compound 23, which proved to be a very potent reversible MAGL inhibitor (IC50 = 80 nM), selective for MAGL over the other main components of the endocannabinoid system, endowed of a promising antiproliferative activity in a series of cancer cell lines and able to block MAGL both in cell-based as well as in vivo assays.

Tankyrase inhibitor

The invention belongs to the technical field of medicines and particularly relates to a tankyrase inhibitor represented by a general formula (I) shown in the description and pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof, wherein R1, R2, R3, m, n, Z, L, Q, A, X1, X2 and Y are as defined in the description. The invention further relates to a preparation method for the compounds, pharmaceutical preparations and pharmaceutical compositions containing the compounds and application of the compound and the pharmaceutically acceptable salts, esters, solvates or stereoisomers thereof in preparation of drugs for treating and/or preventing tankyrase mediated cancers and related diseases.

Substituted N - ((1 °, 3° - [...] - 4° - yl) - methyl) - 4 - benzoyl piperidine compound and use thereof

The invention discloses a substituted N-((1', 3'-azole-4'-yl)-methyl)-4-benzoyl-hexahydropyridine compound represented by formula I, a preparation method thereof, and applications of the substituted N-((1', 3'-oxazole-4'-yl)-methyl)-4-benzoyl-hexahydropyridine compound in preparation of antituberculous drugs. The substituted N-((1', 3'-azole-4'-yl)-methyl)-4-benzoyl-hexahydropyridine compound possesses activity on mycobacterium tuberculosis-susceptible strains, and also possesses activity on strains with tolerance on traditional first-line antituberculous drugs such as isoniazide and rifampicin, and is a novel mycobacterium tuberculosis resistant compound with a promising application prospect.

NOVEL GPR119 AGONIST COMPOUNDS

The present invention relates to novel compounds of formula (I), process for preparation of the same and composition comprising these compounds.

A α, α-diphenyl-4-piperidine methanol synthesis method

The invention discloses a method for synthesis of alpha,alpha-diphenyl-4-piperidine methanol. The method comprises the steps: taking 4-piperidine formic acid as a raw material, carrying out a reaction with an acetylation reagent to obtain N-acetyl piperidine formic acid; firstly generating N-acetyl piperidine formyl chloride from the obtained N-acetyl piperidine formic acid, and then carrying out a Friedel-Crafts acylation reaction with benzene to generate N-acetyl-4-benzoyl piperidine; carrying out a Grignard reaction of the obtained N-acetyl-4-benzoyl piperidine with phenyl magnesium halide to obtain N-acetyl-alpha,alpha-diphenyl-4-piperidine methanol; and deacetylating the N-acetyl-alpha,alpha-diphenyl-4-piperidine methanol to obtain the alpha,alpha-diphenyl-4-piperidine methanol. The synthesis method has the characteristics of cheap and easily obtained raw materials, simple process steps, high reaction yield and low costs of raw materials, and is suitable for industrialized production.

HETEROCYCLIC AMIDES AS KINASE INHIBITORS

Disclosed are compounds having the formula: (I) wherein R1, R2, and R3 are as defined herein, and methods of making and using the same.

TETRAHYDROISOQUINOLINE DERIVED PRMT5-INHIBITORS

A compound of formula I wherein: n is 1 or 2: p is 0 or 1; R1 is optionally one or more halo or methyl groups; R2a and R2b are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R2c and R2d are independently selected from the group consisting of: (i) F; (ii) H; (iii) Me; and (iv) CH2OH; R3a and R3b are independently selected from H and Me; R4 is either H or Me; R5 is either H or Me; R6a and R6b are independently selected from H and Me; A is either (i) optionally substituted phenyl; (ii) optionally substituted naphthyl; or (iii) optionally substituted C5-12 heteroaryl.