153286-94-3

Usage

Uses

Used in Research Applications:
Pyrimidine, 5-ethynyl(9CI) is used as a research compound for exploring its chemical properties and potential applications in medicinal chemistry. The presence of the ethynyl group in the 5th position of the pyrimidine ring may offer unique opportunities for the development of new therapeutic agents or as a tool in biochemical studies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Pyrimidine, 5-ethynyl(9CI) is used as a building block or a starting material for the synthesis of more complex molecules with potential therapeutic applications. Its unique structure may allow for the creation of novel compounds with improved pharmacological properties, such as increased potency, selectivity, or reduced side effects.
Used in Biochemical Studies:
Pyrimidine, 5-ethynyl(9CI) is also used in biochemical studies to investigate its interactions with various biomolecules, such as proteins or enzymes, that are involved in essential cellular processes. Understanding these interactions may provide insights into the compound's potential role in biological systems and its possible applications in the development of new therapeutic strategies.

InChI:InChI=1/C6H4N2/c1-2-6-3-7-5-8-4-6/h1,3-5H

Upstream product

• 216309-28-3 5-[(trimethylsilyl)ethynyl]pyrimidine 
• 584-08-7 potassium carbonate 

Downstream Products

• 157195-66-9 6-Chloro-4-cyclopropyl-1-(4-methoxy-benzyl)-4-pyrimidin-5-ylethynyl-3,4-dihydro-1H-quinazolin-2-one 
• 1012792-61-8 6-pyrimidin-5-ylethynyl-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester 
• 1012792-60-7 6-Pyrimidin-5-yl-ethynyl-5-(4-trifluoromethyl-phenyl)-nicotinic acid ethyl ester 
• 1188490-27-8 (2S,3S,4R,5E,7E)-3-(4-methoxybenzyloxy)-2,4,6-trimethyl-8-(pyrimidin-5-yl)octa-5,7-dien-1-ol 

Relevant academic research and scientific papers

Synthesis of Distorted Nitrogen-Doped Nanographenes by Partially Oxidative Cyclodehydrogenation Reaction

A series of partially fused N-doped nanographenes (2–4) are synthesized via the oxidative cyclodehydrogenation of oligoaryl-substituted dibenzo[e,l]pyrene (1), and five, six, and seven new C?C bonds are formed, respectively, implying stepwise C?C bond fusion and extended π-conjugation. Single-crystal X-ray diffraction analysis of compound 4 a revealed that the presence of sterically demanding groups hindered the formation of planar and fully fused nanographene in the oxidative cyclodehydrogenation reaction step. Optical study of compounds 2 to 4 showed that extended π-conjugation leads to a regular stepwise bathochromic shift in the absorption and emission spectra. Furthermore, the HOMO–LUMO gaps of these compounds exhibit a decrease as C?C bond formation proceeds. Thus, the optoelectronic properties of nanographenes are highly dependent on the formation of new C?C bonds in the molecular skeleton.

Design and characterization of a heterocyclic electrophilic fragment library for the discovery of cysteine-targeted covalent inhibitors

A fragment library of electrophilic small heterocycles was characterized through cysteine-reactivity and aqueous stability tests that suggested their potential as covalent warheads. The analysis of theoretical and experimental descriptors revealed correlations between the electronic properties of the heterocyclic cores and their reactivity against GSH that are helpful in identifying suitable fragments for cysteines with specific nucleophilicity. The most important advantage of these fragments is that they show only minimal structural differences from non-electrophilic counterparts. Therefore, they could be used effectively in the design of targeted covalent inhibitors with minimal influence on key non-covalent interactions.

NOVEL CONDENSED PYRAZOLE DERIVATIVE AND MEDICAL USES THEREOF

PROBLEM TO BE SOLVED: To provide a preventive or therapeutic agent for mood disorder, anxiety disorder, schizophrenia, dementia, drug dependence or the like related to subtypes of metabolism type glutamate receptor (mGlu) 2 and 3. SOLUTION: There are prov

Direct synthesis of α-trifluoromethyl ketone from (hetero)arylacetylene: Design, intermediate trapping, and mechanistic investigations

Regioselective addition across the alkynes has been achieved in a silver-catalyzed protocol utilizing Langlois reagent (CF3SO2Na) and molecular O2 to access medicinally active α-trifluoromethyl ketone compounds. This metho

Rapid discovery of a novel series of Abl kinase inhibitors by application of an integrated microfluidic synthesis and screening platform

Drug discovery faces economic and scientific imperatives to deliver lead molecules rapidly and efficiently. Using traditional paradigms the molecular design, synthesis, and screening loops enforce a significant time delay leading to inefficient use of data in the iterative molecular design process. Here, we report the application of a flow technology platform integrating the key elements of structure-activity relationship (SAR) generation to the discovery of novel Abl kinase inhibitors. The platform utilizes flow chemistry for rapid in-line synthesis, automated purification, and analysis coupled with bioassay. The combination of activity prediction using Random-Forest regression with chemical space sampling algorithms allows the construction of an activity model that refines itself after every iteration of synthesis and biological result. Within just 21 compounds, the automated process identified a novel template and hinge binding motif with pIC50 > 8 against Abl kinase - both wild type and clinically relevant mutants. Integrated microfluidic synthesis and screening coupled with machine learning design have the potential to greatly reduce the time and cost of drug discovery within the hit-to-lead and lead optimization phases.

Discovery of 5-(arenethynyl) hetero-monocyclic derivatives as potent inhibitors of BCR-ABL including the T315I gatekeeper mutant

Ponatinib (AP24534) was previously identified as a pan-BCR-ABL inhibitor that potently inhibits the T315I gatekeeper mutant, and has advanced into clinical development for the treatment of refractory or resistant CML. In this study, we explored a novel series of five and six membered monocycles as alternate hinge-binding templates to replace the 6,5-fused imidazopyridazine core of ponatinib. Like ponatinib, these monocycles are tethered to pendant toluanilides via an ethynyl linker. Several compounds in this series displayed excellent in vitro potency against both native BCR-ABL and the T315I mutant. Notably, a subset of inhibitors exhibited desirable PK and were orally active in a mouse model of T315I-driven CML.

5-PHENYL-NICOTINAMIDE DERIVATIVES

The present invention relates to compounds of the formula wherein R1 to R8 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of

Synthesis of meso-extended tetraarylporphyrins

(Chemical Equation Presented) The synthesis of five new meso-tetraarylporphyrins having pyridine, pyrimidine, or nitrile groups extending tetragonally via alkynyl linkages from the para positions is described. The radial extension is nearly double that of

Arylsulfonamidobenzylic compounds

Arylsulfonamidobenzyl alcohols, amines and sulfonamides are provided which are useful in treating lipid disorders, metabolic diseases and cell-proliferative diseases.

Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidase.

The synthesis of a novel series of 3-phenylprop-2-ynylamines as selective mammalian squalene epoxidase inhibitors is described. Structure activity relationship studies led to the discovery of compound 19, 1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3- methylpiperidine hydrochloride with an IC50 of 2.8 +/- 0.6 microM against rat liver squalene epoxidase. Against 23 strains of fungal squalene epoxidase compound 19 was found to be inactive.