188527-08-4

Basic information

• Product Name: N-Benzyl 1-BOC-piperidine-4-carboxaMide
• Synonyms: N-Benzyl 1-BOC-piperidine-4-carboxaMide;N-benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxamide
• CAS NO: 188527-08-4
• Molecular Formula: C₁₈H₂₆N₂O₃
• Molecular Weight: 318.41064
• Mol File: 188527-08-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Benzyl 1-BOC-piperidine-4-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl 1-BOC-piperidine-4-carboxaMide(188527-08-4)
• EPA Substance Registry System: N-Benzyl 1-BOC-piperidine-4-carboxaMide(188527-08-4)

Safety Data

• Hazardous Substances Data: 188527-08-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Benzyl 1-BOC-piperidine-4-carboxamide is used as a building block for the preparation of various pharmaceutical and agrochemical products. Its structural features allow for the creation of a wide range of compounds with potential applications in these fields.
Used as a Protecting Group in Organic Chemistry:
In the realm of organic chemistry, N-Benzyl 1-BOC-piperidine-4-carboxamide serves as a protecting group for amines. This function is crucial for enabling selective functionalization of other reactive sites in complex organic molecules, thus playing a pivotal role in the synthesis of intricate chemical structures.
Used in Medicinal Chemistry and Drug Discovery:
N-Benzyl 1-BOC-piperidine-4-carboxamide is utilized in medicinal chemistry and drug discovery due to its versatility and the potential for it to be incorporated into new drug candidates. Its presence in the development pipeline underscores its importance in creating novel therapeutic agents.
Used in Chemical Research and Development:
N-Benzyl 1-BOC-piperidine-4-carboxaMide's adaptability makes it a valuable tool in chemical research and development, where it can be employed to explore new reactions, synthesize target molecules, and advance understanding in the field of chemistry.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 498-94-2 isonipecotic acid 
• 100-46-9 benzylamine 
• 280115-99-3 tert-butyl 4-(chlorocarbonyl)-piperidine-1-carboxylate 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 

Downstream Products

• 320420-00-6 N-(phenylmethyl)-4-piperidinecarboxamide hydrochloride 
• 1401618-93-6 N-benzyl-1-(1-(4-chlorobenzyl)-1H-imidazole-2-carbonyl)piperidine-4-carboxamide 
• 896085-01-1 tert-butyl 4-(benzyl(ethyl)carbamoyl)piperidine-1-carboxylate 
• 6308-67-4 N-benzyl-N-ethylpiperidine-4-carboxamide hydrochloride 
• 101264-48-6 4-(phenylmethylaminocarbonyl)piperidine 

Relevant articles and documents

Mitochondrial Cl--Selective Fluorescent Probe for Biological Applications

Herein we describe the development of the first mitochondrial Cl-selective fluorescent probe, Mito-MQAE, and its applications in biological systems. Fluorescence of Mito-MQAE is insensitive to pH over the physiological pH range and is quenched by Cl- with a Stern-Volmer quenching constant of 201 M-1 at pH 7.0. The results of cell studies using Mito-MQAE show that substances with the ability to disrupt mitochondrial membranes cause increases in the mitochondrial Cl- concentration.

NEW HETEROCYCLIC COMPOUNDS AS MONOACYLGLYCEROL LIPASE INHIBITORS

The invention provides new heterocyclic compounds having the general formula (I) wherein A, L, X, m, n, R1 and R2 are as described herein, compositions including the compounds, processes of manufacturing the compounds, methods of using the compounds and methods of determining the monoacylglycerol lipase (MAGL) inhibitory activity of the compounds.

NEW HETEROCYCLIC COMPOUNDS AS MONOACYLGLYCEROL LIPASE INHIBITORS

The invention provides new heterocyclic compounds having the general formula (I) wherein A, L, X, m, n, R1 and R2 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.

Design, synthesis, biological evaluation and molecular docking study of arylcarboxamido piperidine and piperazine-based hydroxamates as potential HDAC8 inhibitors with promising anticancer activity

HDAC8 has been established as one of the vital targets as far as the cancer is concerned. Different compounds having potential HDAC inhibitory activity have been approved by USFDA. However, none of these compounds are selective towards specific HDAC isoform. In this current study, some new hydroxamate derivatives with alkylpiperidine and alkylpiperazine linker moieties have been designed, synthesized and biologically evaluated. All these compounds are effective HDAC8 inhibitors comprising more or less similar cytotoxic potential against different cancer cell lines. It is observed that the piperazine scaffold containing compound is more active than the compound with piperidine scaffold for exerting HDAC8 inhibitory activity. Moreover, the 4-quinolyl cap group is better than the biphenyl group which is better than the benzyl group for producing higher HDAC8 inhibition as well as cytotoxicity. These compounds displayed selective HDAC8 inhibition over HDAC3. Moreover, these compounds showed an increased caspase3/7 activity suggesting their anticancer potential through modulation of apoptotic pathways. Molecular docking study with three potent compounds was performed with both HDAC3 and HDAC8 enzymes to understand the selectivity profile of these compounds. Compound containing 4-quinolyl cap group with alkyl piperazinyl urea linker moiety has been emerged out as the lead molecule that may be further modified to design more effective and selective HDAC8 inhibitors in future.

SUBSTITUTED PYRAZOLO[1,5-A]PYRIDINE COMPOUNDS AS RET KINASE INHIBITORS

Provided herein are compounds of the Formula I: (I) or pharmaceutically acceptable salt or solvate thereof, wherein A, B, X1, X2, X3, X4, Ring D, E, Ra, Rb, n and m have the meanings given in the specification, which are inhibitors of RET kinase and are useful in the treatment and prevention of diseases which can be treated with a RET kinase inhibitor, including RET-associated diseases and disorders.

Trisubstituted thieno[3,2-b]pyrrole 5-carboxamides as potent inhibitors of alphaviruses

Chikungunya virus (CHIKV) is a re-emerging vector-borne alphavirus and is transmitted to humans by Aedes mosquitoes. Despite the re-emergence of CHIKV as an epidemic threat, there is no approved effective antiviral treatment currently available for CHIKV. Herein, we report the synthesis and structure-activity relationship studies of a class of thieno[3,2-b]pyrroles and the discovery of a trisubstituted thieno[3,2-b]pyrrole 5-carboxamide 15c that exhibits potent inhibitory activity against in vitro CHIKV infection. Compound 15c displayed low micromolar activity (EC50 value of ca. 2 μM) and limited cytotoxic liability (CC50 > 100 μM) therefore furnishing a selectivity index of greater than 32. Notably, 15c not only controlled viral RNA production, but efficiently inhibited the expression of CHIKV nsP1, nsP3, capsid, and E2 proteins at a concentration as low as 2.5 μM. More importantly, 15c also demonstrated broad spectrum antiviral activity against other clinically important alphaviruses such as O'nyong-nyong virus and Sindbis virus.

Development of a highly potent, novel M5positive allosteric modulator (PAM) demonstrating CNS exposure: 1-((1H-indazol-5-yl)sulfoneyl)-N-ethyl-N-(2-(trifluoromethyl)benzyl)piperidine-4-carboxamide (ML380)

A functional high throughput screen identified a novel chemotype for the positive allosteric modulation (PAM) of the muscarinic acetylcholine receptor (mAChR) subtype 5 (M5). Application of rapid analog, iterative parallel synthesis efficiently optimized M5potency to arrive at the most potent M5PAMs prepared to date and provided tool compound 8n (ML380) demonstrating modest CNS penetration (human M5EC50= 190 nM, rat M5EC50= 610 nM, brain to plasma ratio (Kp) of 0.36).

Design, synthesis, and biological evaluation of novel piperidine-4- carboxamide derivatives as potent CCR5 inhibitors

Based on a putative 'Y shape' pharmacophore model of CCR5 inhibitors, a series of novel piperidine-4-carboxamide derivatives were designed and synthesized using a group-reverse strategy. Among synthesized target compounds, 16g (IC50 = 25.73 nM) and 16i (IC50 = 25.53 nM) showed equivalent inhibitory activity against CCR5 to that of the positive control maraviroc (IC50 = 25.43 nM) in calcium mobilization assay. Selected compounds were further tested for their antiviral activity in HIV-1 single cycle assay. Two compounds, 16g and 16i, displayed antiviral activity with IC 50 values of 73.01 nM and 94.10 nM, respectively. Additionally, the pharmacokinetic properties and inhibitory potency against hERG of 16g were evaluated, providing a foundation for ongoing optimization.

ARBOVIRUS INHIBITORS AND USES THEREOF

The present invention relates to chemical compounds, methods for their discovery, and their therapeutic use. In particular, the present invention provides compounds as inhibitors of arboviruses.

Discovery of N-{1-[3-(3-Oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl] piperidin-4-yl}-2-phenylacetamide (Lu AE51090): An allosteric muscarinic M 1 receptor agonist with unprecedented selectivity and procognitive potential

The discovery and Structure-activity relationship (SAR) of a series of allosteric muscarinic M1 receptor agonists are described. Compound 17 (Lu AE51090) was identified as a representative compound from the series, based on its high selectivity as an agonist at the muscarinic M1 receptor across a panel of muscarinic receptor subtypes. Furthermore, 17 displayed a high degree of selectivity when tested in a broad panel of G-protein-coupled receptors, ion channels, transporters, and enzymes, and 17 showed an acceptable pharmacokinetic profile and sufficient brain exposure in rodents in order to characterize the compound in vivo. Hence, in a rodent model of learning and memory, 17 reversed delay-induced natural forgetting, suggesting a procognitive potential of 17.