5515-14-0

Usage

Uses

Used in Organic Synthesis:
[(4-Chlorophenyl)methoxymethylene]propanedinitrile is utilized as a building block in organic synthesis, allowing for the creation of various compounds. Its 4-chlorophenyl group enhances reactivity and facilitates the introduction of different functional groups, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, [(4-Chlorophenyl)methoxymethylene]propanedinitrile serves as a starting material for the preparation of heterocyclic compounds and pharmaceutical intermediates. Its unique structure and reactivity contribute to the development of novel drug candidates and therapeutic agents.
Safety Precautions:
It is crucial to handle [(4-Chlorophenyl)methoxymethylene]propanedinitrile with care due to its potential health and safety hazards. Proper safety measures should be taken to minimize risks associated with its use in research and industrial applications.

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 5593-28-2 2-((4-chlorophenyl)(hydroxy)methylene)malononitrile 
• 67-68-5 dimethyl sulfoxide 
• 77-78-1 dimethyl sulfate 
• 46290-15-7 p-chlorobenzoylmalononitrile 

Downstream Products

• 99979-11-0 (α-aziridin-1-yl-4-chloro-benzylidene)-malononitrile 
• 107058-38-8 (4-chloro-α-piperidino-benzylidene)-malononitrile 
• 106595-19-1 (4-chloro-α-[2]pyridylamino-benzyl)-malononitrile 
• 98949-15-6 2-(amino(4-chlorophenyl)methylene)malononitrile 
• 98949-16-7 5-amino-3-(4-chlorophenyl)isoxazole-4-carbonitrile 
• 81067-01-8 2-Amino-4-(4-chloro-phenyl)-6-methoxy-pyrimidine-5-carbonitrile 
• 81067-06-3 2-Amino-4-(4-chloro-phenyl)-6-ethoxy-pyrimidine-5-carbonitrile 
• 95893-23-5 6-Amino-5-benzenesulfonyl-4-(4-chloro-phenyl)-2-methoxy-nicotinonitrile 
• 180903-14-4 5-amino-1-tert-butyl-3-(p-chlorophenyl)-4-cyanopyrazole 
• 180903-15-5 5-amino-3-(p-chlorophenyl)-4-cyano-1-cyclohexylpyrazole 
• 1354825-96-9 C₂₃H₂₃ClN₆O₂ 
• 1354825-97-0 BrH*C₁₅H₁₇ClN₆ 
• 111510-09-9 5-amino-1-phenyl-3-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile 
• 129852-42-2 4-Amino-3-(4-chlorophenyl)-1-phenylpyrazolo<3,4-d>pyrimidine 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of proteolysis targeting chimeras (PRoTACS) for the dual degradation of IGF-1R and SrC

A focused PROTAC library was developed to degrade both IGF-1R and Src proteins, which are associated with various cancers. PROTACs with IGF-1R and Src degradation potentials were synthesized by tethering different inhibitor warhead units and the E3 ligase (CRBN) recruiting-pomalidomide with various linkers. The designed PROTACs 12a–b inhibited the proliferation and migration of MCF7 and A549 cancer cells with low micromolar potency (1–5 μM) in various cellular assays.

Converting a weaker ATP-binding site inhibitor into a potent hetero-bivalent ligand by tethering to a unique peptide sequence derived from the same kinase

Attaching an additional binding site directed moiety or a ligand to an ATP-binding site inhibitor has been used as a strategy to increase kinase binding affinity and specificity. The moieties typically used here as the second binding partner are varied from simple organic groups to ligands such as peptides derived from substrate binding site sequences. So far these hetero-bivalent ligands were developed targeting additional binding sites closer to the ATP-binding pocket. Here we report a unique expansion of this hetero-bivalent idea by: (I) targeting a new binding site much farther away from ATP-binding site, (II) using a peptide uniquely derived from a portion of the same kinase sequence that has been reported to turn and bind to the above distance binding pocket (used as the second binding ligand), and (III) optimizing a much longer and flexible linker (to connect ATP-binding site inhibitor and above mentioned second peptide sequence) with multistep, yet complete on-bead synthesis approach. We converted a very weak EphA3-kinase ATP-binding site inhibitor-PP2 into a potent hetero-bivalent ligand by tethering to a unique 5-mer peptide sequence that derived from the linker region of EphA3 that connects kinase and sterile alpha motif (SAM) domains. Our design highlight the use of distance binding pockets to ATP-binding site as the second targeted site, while introducing the idea of extracting natural peptide sequences that already exist within the same kinase sequence, by a careful screening of available crystal structures.

Studies on the ATP Binding Site of Fyn Kinase for the Identification of New Inhibitors and Their Evaluation as Potential Agents against Tauopathies and Tumors

Fyn is a member of the Src-family of nonreceptor protein-tyrosine kinases. Its abnormal activity has been shown to be related to various human cancers as well as to severe pathologies, such as Alzheimer's and Parkinson's diseases. Herein, a structure-based drug design protocol was employed aimed at identifying novel Fyn inhibitors. Two hits from commercial sources (1, 2) were found active against Fyn with Ki of about 2 μM, while derivative 4a, derived from our internal library, showed a Ki of 0.9 μM. A hit-to-lead optimization effort was then initiated on derivative 4a to improve its potency. Slightly modifications rapidly determine an increase in the binding affinity, with the best inhibitors 4c and 4d having Kis of 70 and 95 nM, respectively. Both compounds were found able to inhibit the phosphorylation of the protein Tau in an Alzheimer's model cell line and showed antiproliferative activities against different cancer cell lines. (Chemical Equation Presented).

PROTEIN KINASE INHIBITORS AND METHODS OF TREATMENT

The present invention relates to chemical compounds of formula (I) and methods for their use and preparation. In particular, the invention relates to substituted pyrazolo[3,4-d]pyrimidine based compounds which can be used in treating proliferative disorders, use of these compounds in methods of therapy and the manufacture of medicaments as well as compositions containing these compounds.

One-pot synthesis of tetrasubstituted pyrazoles - Proof of regiochemistry

1-Alkyl-5-amino-3-aryl-4-cyanopyrazoles, useful intermediates for fused heterocyclic systems, are synthesised by a one-pot three-step procedure from acid chlorides, malononitrile and alkylhydrazines. The regiochemistry of the hydrazine incorporation was p