N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-2-cyanoacetamide
[CAS# 915945-31-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-2-cyanoacetamide
• Molecular Formula: C₁₅H₁₂ClN₃O₂
• Molecular Weight: 301.73
• CAS Registry Number: 915945-31-2
• SMILES: C1=CC=NC(=C1)COC2=C(C=C(C=C2)NC(=O)CC#N)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.631, Calc.^*
• Boiling Point: 553.0±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 288.3±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-2-cyanoacetamide, commonly known as CPAC, is a synthetic chemical compound that has attracted much attention in the field of medicinal chemistry and drug development for its potential pharmacological applications. The discovery of CPAC stems from the exploration of cyanoacetamide derivatives, which have various biological activities, including antibacterial, antiviral, and anticancer properties. Researchers aim to enhance these properties by adding specific functional groups such as chlorine and pyridin-2-ylmethoxy groups to the benzene ring adjacent to the cyanoacetamide group. The cyanoacetamide group confers reactivity and biological activity, often involved in enzyme inhibition and cellular pathways. Substituted benzene rings enhance pharmacological properties by interacting with target proteins or receptors. Chlorine and pyridin-2-ylmethoxy groups contribute to the specificity and affinity of the compound for biological targets.

CPAC exhibits promising anticancer activity by interfering with cell cycle regulation and inducing apoptosis in cancer cells. Its ability to target specific molecular pathways makes it a candidate for cancer therapy, especially in the treatment of solid tumors and hematological malignancies. The compound has antimicrobial properties against a variety of pathogens, including bacteria and fungi. It may inhibit microbial growth by disrupting essential cellular processes, suggesting that it could be used to combat infectious diseases.

CPAC has been extensively studied for its neuroprotective properties, potentially mitigating neuronal damage and inflammation associated with neurodegenerative diseases such as Alzheimer's and Parkinson's. It may modulate oxidative stress and inflammatory responses in neuronal cells, thereby treating neurological disorders.

CPAC is a lead structure in drug discovery efforts, guiding the synthesis of analogs with optimized pharmacokinetic and pharmacodynamic characteristics. Structural modifications can enhance their potency, selectivity, and bioavailability for specific therapeutic applications. Researchers have used CPAC in SAR studies to identify key structural features that influence their bioactivity. This information provides a reference for the rational design of new compounds with higher efficacy and fewer side effects.