216985-30-7

Basic information

• Product Name: 4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester
• Synonyms: ethyl 1-(4-nitrophenyl)-4-piperidinecarboxylate;1-(4-Nitrophenyl)piperidine-4-carboxylic acid ethyl ester;4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester
• CAS NO: 216985-30-7
• Molecular Formula: C₁₄H₁₈N₂O₄
• Molecular Weight: 278.3
• Mol File: 216985-30-7.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester(216985-30-7)
• EPA Substance Registry System: 4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester(216985-30-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 216985-30-7(Hazardous Substances Data)

Usage

Description

4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester, also known as Ethyl 1-(4-Nitrophenyl)-4-piperidinecarboxylate, is an organic compound derived from the piperidine family. It is characterized by its ester functional group and a nitrophenyl moiety attached to the piperidine ring. 4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester serves as an important intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
4-Piperidinecarboxylic acid, 1-(4-nitrophenyl)-, ethyl ester is used as a key intermediate in the synthesis of Imidazopyridazine derivatives. These derivatives are known as PDE10a inhibitors, which play a crucial role in the treatment of diabetes. By inhibiting PDE10a, these compounds help regulate the levels of cyclic nucleotides, thereby improving the overall glucose homeostasis in the body.
Additionally, this compound may also be utilized in the development of other therapeutic agents targeting different diseases, given its structural versatility and potential for further chemical modifications.

Upstream product

• 1126-09-6 4-carbethoxypiperidine 
• 350-46-9 4-Fluoronitrobenzene 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 471937-85-6 [1-(4-Nitrophenyl)piperidin-4-yl]-methanol 
• 439095-52-0 ethyl 1-(4-aminophenyl)piperidine-4-carboxylate 
• 223786-53-6 1-(4-nitrophenyl)piperidine-4-carboxylic acid 
• 927878-50-0 C₁₆H₂₁N₃O₄ 
• 1444001-33-5 (R)-ethyl 1-(4-(5-((1,3-dioxoisoindolin-2-yl)methyl)-2-oxooxazolidin-3-yl)phenyl)piperidine-4-carboxylate 
• 1444001-38-0 (R)-ethyl 1-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)piperidine-4-carboxylate 
• 1444001-41-5 ethyl 1-(4-((S)-5-((2-((tert-butoxycarbonyl)amino)thiazole-5-carboxamido)methyl)-2-oxooxazolidin-3-yl)phenyl)-2-oxopiperidine-4-carboxylate 
• 1444001-52-8 (R)-ethyl 1-(4-(2-oxo-5-((4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzamido)methyl)oxazolidin-3-yl)phenyl)piperidine-4-carboxylate 
• 1444001-53-9 (R)-ethyl 1-(4-(2-oxo-5-(((4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzyl)amino)methyl)oxazolidin-3-yl)phenyl)piperidine-4-carboxylate 

Relevant articles and documents

Transformation of a selective factor Xa inhibitor rivaroxaban into a dual factor Xa/thrombin inhibitor by modification of the morpholin-3-one moiety

Replacement of the P4 morpholin-3-one moiety in a selective factor Xa inhibitor rivaroxaban by 2-ethoxycarbonylpiperidine resulted in a dual factor Xa/thrombin inhibitor 24, possessing a Ki of 62 ± 18 nM for factor Xa and a Ki/

New N-phenyl-4,5-dibromopyrrolamides and N-Phenylindolamides as ATPase inhibitors of DNA gyrase

Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 μM against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds - especially by varying their size, the position and orientation of key functional groups, and their acid-base properties. The structure-activity relationship (SAR) was examined and the results were rationalised with molecular docking.

PDE 10a Inhibitors for the Treatment of Type II Diabetes

Disclosed are compounds, compositions and methods for treating Type II diabetes. Such compounds are represented by Formula (I) as follows: wherein R1, R2, L, and Q are defined herein.