945619-31-8

Basic information

• Product Name: PIK 75
• Synonyms: 2-Methyl-5-nitrobenzenesulfonic acid (2E)-2-[(6-bromoimidazo[1,2-a]pyridin-3-yl)methylene]-1-methylhydrazide;cis-PIK 75;cis-PIK 75 2-Methyl-5-nitrobenzenesulfonic acid (2E)-2-[(6-bromoimidazo[1,2-a]pyridin-3-yl)methylene]-1-methylhydrazide;Benzenesulfonic acid, 2-methyl-5-nitro-, (2E)-2-[(6-bromoimidazo[1,2-a]pyridin-3-yl)methylene]-1-methylhydrazide;N-[(E)-(6-bromoimidazo[1,2-a]pyridin-3-yl)methylideneamino]-N,2-dimethyl-5-nitrobenzenesulfonamide
• CAS NO: 945619-31-8
• Molecular Formula: C16H14BrN5O4S
• Molecular Weight: 452.28246
• Mol File: 945619-31-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.66
• CAS DataBase Reference: PIK 75(CAS DataBase Reference)
• NIST Chemistry Reference: PIK 75(945619-31-8)
• EPA Substance Registry System: PIK 75(945619-31-8)

Safety Data

• Hazardous Substances Data: 945619-31-8(Hazardous Substances Data)

Usage

Description

PIK 75, a potent and selective inhibitor of phosphatidylinositol 3-kinase (PI3K), is a promising compound in the field of cancer treatment. It functions by inhibiting the activity of the PI3K enzyme, which is crucial for cell growth, proliferation, and survival. The inhibition of PI3K by PIK 75 leads to cell cycle arrest and the promotion of apoptosis in cancer cells, positioning it as a potential candidate for targeted cancer therapy. Moreover, PIK 75 exhibits anti-inflammatory and anti-angiogenic effects, broadening its therapeutic potential for a range of diseases. Further research is essential to fully understand its pharmacological properties and explore its clinical applications.

Uses

Used in Cancer Therapy:
PIK 75 is used as a targeted cancer therapy agent for its ability to induce cell cycle arrest and promote apoptosis in cancer cells by inhibiting the PI3K enzyme. This makes it a potential candidate for the treatment of various types of cancer.
Used in Anti-inflammatory Applications:
PIK 75 is used as an anti-inflammatory agent due to its capacity to reduce inflammation, which can be beneficial in managing inflammatory conditions and diseases.
Used in Anti-angiogenic Applications:
PIK 75 is utilized as an anti-angiogenic agent to prevent the formation of new blood vessels, which is particularly useful in inhibiting the growth of tumors by cutting off their blood supply.
Used in Pharmaceutical Research:
PIK 75 is used as a research tool in the development of new drugs and therapies, particularly in the areas of oncology, inflammation, and angiogenesis, to better understand its pharmacological properties and potential clinical applications.

Upstream product

• 30384-96-4 6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde 
• 121-02-8 2-methyl-5-nitrobenzene-1-sulfonyl chloride 
• 60-34-4 methylhydrazine 
• 945619-40-9 N'-((6-bromoimidazo[1,2-a]pyridin-3-yl)methylene)-2-methyl-5-nitrobenzenesulfonohydrazide 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 

Relevant articles and documents

An Unusual Intramolecular Halogen Bond Guides Conformational Selection

PIK-75 is a phosphoinositide-3-kinase (PI3K) α-isoform-selective inhibitor with high potency. Although published structure–activity relationship data show the importance of the NO2 and the Br substituents in PIK-75, none of the published studies could correctly determine the underlying reason for their importance. In this publication, we report the first X-ray crystal structure of PIK-75 in complex with the kinase GSK-3β. The structure shows an unusual U-shaped conformation of PIK-75 within the active site of GSK-3β that is likely stabilized by an atypical intramolecular Br???NO2 halogen bond. NMR and MD simulations show that this conformation presumably also exists in solution and leads to a binding-competent preorganization of the PIK-75 molecule, thus explaining its high potency. We therefore suggest that the site-specific incorporation of halogen bonds could be generally used to design conformationally restricted bioactive substances with increased potencies.

Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110α inhibitors

We have previously reported the imidazo[1,2-a]pyridine derivative 4 as a novel p110α inhibitor; however, although 4 is a potent inhibitor of p110α enzymatic activity and tumor cell proliferation in vitro, it is unstable in solution and ineffective in vivo