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Usage

Uses

Used in Pharmaceutical Industry:
4-Ethynyltetrahydro-2H-pyran is used as a key intermediate in the synthesis of aminopyrazine derivatives, which are known for their potential as PI3k-γ inhibitors. PI3k-γ is an enzyme that plays a crucial role in various cellular processes, including cell growth, survival, and migration. Inhibition of this enzyme has been shown to have therapeutic benefits in treating various diseases, particularly those related to inflammation and cancer.
In the synthesis of these aminopyrazine derivatives, the ethynyl group of 4-Ethynyltetrahydro-2H-pyran can be further functionalized or modified to introduce different substituents or functional groups, which can enhance the biological activity and selectivity of the resulting compounds. This makes 4-Ethynyltetrahydro-2H-pyran a valuable building block in the development of novel PI3k-γ inhibitors with improved pharmacological properties and therapeutic potential.
Additionally, the unique structural features of 4-Ethynyltetrahydro-2H-pyran may also allow it to be used in the development of other bioactive molecules with diverse applications in the pharmaceutical industry. Its versatility in chemical reactions and compatibility with various functional groups make it a promising candidate for the synthesis of a wide range of compounds with potential therapeutic applications.

Upstream product

• 40191-32-0 tetrahydro-2H-pyran-4-carbonylchloride 
• 50675-18-8 3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 14774-37-9 (tetrahydro-2H-pyran-4-yl)methanol 

Relevant academic research and scientific papers

Synthesis, structure and pyrolysis of stabilised phosphonium ylides containing saturated oxygen heterocycles

A range of twelve stabilised phosphonium ylides containing tetrahydrofuran, tetrahydropyran or 2,2-dimethyl-1,3-dioxolane rings have been prepared and fully characterised, including one X-ray structure determination of each type. The X-ray structures confirm the P=C and C=O functions to be syn and all the compounds undergo thermal extrusion of Ph3PO to give the corresponding alkynes. In some cases there is also competing loss of Ph3P to give different carbene-derived products and evidence has been obtained for the generation of 2-phenyloxete in this way. Raising the pyrolysis temperature leads in several cases to new secondary reactions of the alkyne products involving a sequence of alkyne to vinylidene isomerisation, intramolecular CH insertion, and retro Diels Alder reaction.

SULFONYL-SUBSTITUTED BICYCLIC COMPOUND WHICH ACTS AS ROR INHIBITOR

Provided is a sulfonyl-substituted bicyclic compound (A) which acts as a RORγ inhibitor, said compound has good RORγ inhibitory activity and is expected to be used for treating diseases mediated by a RORγ receptor in mammals.

Difluorocyclobutylacetylenes as positive allosteric modulators of mGluR5 with reduced bioactivation potential

Schizophrenia is a serious illness that affects millions of patients and has been associated with N-methyl-D-aspartate receptor (NMDAR) hypofunction. It has been demonstrated that activation of metabotropic glutamate receptor 5 (mGluR5) enhances NMDA receptor function, suggesting the potential utility of mGluR5 positive allosteric modulators (PAMs) in the treatment of schizophrenia. Herein we describe the optimization of an mGluR5 PAM by replacement of a phenyl with aliphatic heterocycles and carbocycles as a strategy to reduce bioactivation in a biaryl acetylene chemotype. Replacement with a difluorocyclobutane followed by further optimization culminated in the identification of compound 32, a low fold shift PAM with reduced bioactivation potential. Compound 32 demonstrated favorable brain uptake and robust efficacy in mouse novel object recognition (NOR) at low doses.