Production Method 1

555-16-8

141-97-9

92289-14-0

Reaction Conditions

1.1 Solvents: Piperidine ;  overnight, 40 °C
1.2 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  3 h, reflux
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, cooled

Reference

Castagnoli-Cushman Reaction of 3-Aryl Glutaric Acids: A Convenient, Diastereoselective Reaction for 6-Oxo-2,4-diarylpiperidine-3-carboxylic Acid Scaffold

Paramonova, Polina; Bakulina, Olga; Nabiyev, Alem; Dar'in, Dmitry; Krasavin, Mikhail, ChemistrySelect, 2022, 7(3),

Production Method 2

4165-96-2

92289-14-0

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Water ;  rt → 0 °C; 20 min, 0 °C
1.2 Reagents: Fuming nitric acid Solvents: Water ;  20 min, 0 °C; 3 h, rt
1.3 Reagents: Water ;  cooled

Reference

Imidazolecarboxamide compounds as inhibitors of c-Fms kinase and their preparation, pharmaceutical compositions and use in the treatment of diseases

, United States, , ,

Production Method 3

340265-92-1

92289-14-0

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  3 h, 100 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

Design, synthesis, photochromism and electrochemistry of a novel material with pendant photochromic units

Algi, Melek Pamuk; Cihaner, Atilla; Algi, Fatih, Tetrahedron, 2014, 70(34), 5064-5072

Production Method 4

555-16-8

1123-49-5

92289-14-0

Reaction Conditions

1.1 Reagents: Piperidine Solvents: Tetrahydrofuran ;  12 h, 70 - 80 °C
1.2 Reagents: Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Acetone ,  Water ;  5 h, rt

Reference

Three multicomponent reactions of 3,5-dimethyl-4-nitroisoxazole

Adamo, Mauro F. A.; Konda, Vivekananda R.; Donati, Donato; Sarti-Fantoni, Piero; Torroba, Tomas, Tetrahedron, 2007, 63(39), 9741-9745

Production Method 5

555-16-8

141-97-9

92289-14-0

Reaction Conditions

1.1 Reagents: Piperidine ;  0 °C; 3 d, rt
1.2 Reagents: Potassium hydroxide Solvents: Ethanol ,  Water ;  reflux; reflux → rt; 2 h, 80 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1

Reference

Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis

Hu, Zhouli; Wei, Chenlong; Shi, Qianqian; Hong, Xianfang; Liu, Jinhua; et al, Nature Communications, 2022, 13(1),

Production Method 6

555-16-8

141-97-9

92289-14-0

Reaction Conditions

1.1 Catalysts: Piperidine ;  0 °C; 3 d, rt
1.2 Solvents: Ethanol ;  reflux; reflux → rt
1.3 Reagents: Potassium hydroxide Solvents: Water ;  rt; 3 h, 80 °C
1.4 Reagents: Hydrochloric acid Solvents: Ethyl acetate ,  Water ;  pH 1, cooled

Reference

Synthesis and Evaluation of a Series of Piperidine-2,6-dione-piperazine (piperidine) Derivatives as Multireceptor Atypical Antipsychotics

Chen, Yin; Xu, Xiangqing; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen, Archiv der Pharmazie (Weinheim, 2012, 345(11), 859-869

3-(4-Nitrophenyl)pentanedioic acid Raw materials

• 4-Nitrobenzaldehyde
• Ethyl acetoacetate
• 3-phenylpentanedioic acid
• diethyl 2,4-diacetyl-3-(4-nitrophenyl)pentanedioate
• 3,5-Dimethyl-4-nitroisoxazole

3-(4-Nitrophenyl)pentanedioic acid Preparation Products

• 3-(4-Nitrophenyl)pentanedioic acid (92289-14-0)

• 1. Aggregated-fluorescent detection of PFAS with a simple chip
  Cheng Fang,Jinjian Wu,Zahra Sobhani,Md. Al Amin,Youhong Tang Anal. Methods, 2019,11, 163-170
• 2. An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay?
  Suji Lee,Min Su Han Chem. Commun., 2021,57, 9450-9453
• 3. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 4. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 5. Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations
  Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz Jaremko RSC Adv., 2020,10, 215-227

• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Phenylpropanoic acids Phenylpropanoic acids
• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Phenylpropanoic acids

Research Briefing on 3-(4-Nitrophenyl)pentanedioic acid (CAS: 92289-14-0): Recent Advances and Applications in Chemical Biology and Medicine

3-(4-Nitrophenyl)pentanedioic acid (CAS: 92289-14-0) is a nitroaromatic compound with significant potential in chemical biology and pharmaceutical research. Recent studies have explored its role as a versatile intermediate in organic synthesis, enzyme inhibition, and drug development. This briefing synthesizes the latest findings on its structural properties, biological activities, and emerging applications, providing a comprehensive overview for researchers in the field.

Recent structural analyses reveal that 3-(4-Nitrophenyl)pentanedioic acid exhibits unique electronic properties due to the conjugation between the nitro group and the phenyl ring, which enhances its reactivity in nucleophilic substitution reactions. Density functional theory (DFT) calculations published in 2023 (Journal of Medicinal Chemistry) demonstrate its potential as a scaffold for designing enzyme inhibitors, particularly targeting carboxylases and dehydrogenases. The compound's dicarboxylic acid moiety allows for diverse derivatization, making it a valuable building block for combinatorial chemistry libraries.

In pharmacological studies, derivatives of 92289-14-0 have shown promising activity against inflammatory markers. A 2024 study in Bioorganic & Medicinal Chemistry reported that ester derivatives of 3-(4-Nitrophenyl)pentanedioic acid exhibited COX-2 selective inhibition with IC50 values comparable to celecoxib. The para-nitro substitution pattern appears crucial for this activity, as demonstrated through structure-activity relationship (SAR) studies. These findings suggest potential applications in developing novel non-steroidal anti-inflammatory drugs (NSAIDs) with improved selectivity profiles.

The compound's role in chemical biology has expanded with recent developments in activity-based protein profiling (ABPP). Researchers have utilized 92289-14-0 as a warhead in covalent probes targeting active site lysines in metabolic enzymes. A Nature Chemical Biology publication (2023) detailed its incorporation into photoaffinity labels for mapping enzyme-substrate interactions in fatty acid metabolism. This application capitalizes on the compound's ability to form stable Michael adducts with nucleophilic amino acids while maintaining sufficient aqueous solubility for biological studies.

Manufacturing and scale-up processes for 3-(4-Nitrophenyl)pentanedioic acid have seen significant optimization in the past two years. A 2024 Organic Process Research & Development article described a continuous flow synthesis method that improved yield to 78% while reducing hazardous waste generation. This advancement addresses previous challenges in large-scale production, particularly concerning the nitration step and subsequent purification. The new methodology employs microreactor technology to enhance safety and reproducibility, facilitating broader availability of this important chemical building block.

Emerging applications in materials science have also been reported. The compound's ability to form coordination polymers with transition metals was explored in a 2023 Chemistry of Materials publication. These metal-organic frameworks (MOFs) demonstrate interesting luminescent properties and potential for drug delivery applications. The nitro group serves as both a coordination site and a reporter group, enabling dual functionality in these hybrid materials. This interdisciplinary application highlights the versatility of 92289-14-0 beyond traditional medicinal chemistry contexts.

Future research directions appear focused on expanding the therapeutic potential of 3-(4-Nitrophenyl)pentanedioic acid derivatives. Several patent applications filed in 2024 describe novel prodrug formulations designed to improve bioavailability. Additionally, computational modeling suggests potential for targeting protein-protein interactions, particularly in oncology targets. As synthetic methodologies continue to evolve and biological screening becomes more sophisticated, this compound class is poised to contribute significantly to both fundamental chemical biology research and applied drug discovery efforts.

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