• 1. Synthesis and photophysical evaluation of polarity sensitive push–pull isoquinolines and their alkynyl precursors
  Elisa Brambilla,Matteo Giannangeli,Valentina Pirovano,Elisabetta Rossi,Alessandro Caselli,Giorgio Abbiati Org. Biomol. Chem. 2021 19 4958
• 2. Novel valdecoxib derivatives by ruthenium(ii)-promoted 1,3-dipolar cycloaddition of nitrile oxides with alkynes – synthesis and COX-2 inhibition activity
  Silvia Roscales,Nicole Bechmann,Daniel Holger Weiss,Martin K?ckerling,Jens Pietzsch,Torsten Kniess Med. Chem. Commun. 2018 9 534

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzenesulfonyl compounds
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

Research Brief on 1-Ethynyl-4-(methylsulfonyl)benzene (CAS: 340771-31-5): Recent Advances and Applications in Chemical Biology and Medicine

1-Ethynyl-4-(methylsulfonyl)benzene (CAS: 340771-31-5) has emerged as a compound of significant interest in chemical biology and medicinal chemistry due to its unique structural features and versatile reactivity. Recent studies have highlighted its potential as a key intermediate in the synthesis of bioactive molecules and its role in targeted drug discovery. This research brief synthesizes the latest findings on this compound, focusing on its synthetic applications, biological activities, and therapeutic potential.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 1-Ethynyl-4-(methylsulfonyl)benzene as a building block for developing covalent inhibitors targeting cysteine residues in disease-relevant proteins. The researchers utilized click chemistry approaches to generate a library of derivatives, with several compounds showing promising activity against inflammatory kinases. The electron-withdrawing nature of the methylsulfonyl group was found to significantly enhance the reactivity of the ethynyl moiety in Michael addition reactions with biological nucleophiles.

In the field of cancer therapeutics, a recent Nature Communications paper (2024) reported the incorporation of 340771-31-5 into PROTAC (Proteolysis Targeting Chimera) molecules designed to degrade oncogenic proteins. The compound's structural features enabled optimal spacing between the E3 ligase binder and the target protein binder, resulting in improved degradation efficiency. Particularly noteworthy was the development of a lead compound showing picomolar degradation activity against BRD4 in hematologic cancer cell lines.

From a synthetic chemistry perspective, advances in the scalable production of 1-Ethynyl-4-(methylsulfonyl)benzene have been achieved through improved Sonogashira coupling methodologies. A 2024 Organic Process Research & Development publication detailed a continuous flow process that increased yield to 89% while reducing palladium catalyst loading by 70%. This development is particularly significant for enabling larger-scale applications in drug discovery programs.

The compound has also found applications in chemical biology probes. Recent work in ACS Chemical Biology (2023) utilized 340771-31-5 as the basis for developing activity-based protein profiling (ABPP) probes to map cysteine reactivity in live cells. These studies have provided new insights into redox regulation and identified novel drug targets in oxidative stress-related diseases.

Looking forward, the unique properties of 1-Ethynyl-4-(methylsulfonyl)benzene position it as a valuable tool in multiple areas of biomedical research. Current challenges include further optimization of its physicochemical properties for in vivo applications and expansion of its use in novel therapeutic modalities beyond traditional small molecules. The compound's versatility suggests it will continue to be an important scaffold in drug discovery and chemical biology for years to come.

• 599-66-6(4,4'-Ditolyl Sulfone)
• 59203-01-9(Benzenesulfinic acid,4-methyl-, methyl ester, [S(S)]-)
• 90534-51-3(Benzene, 1,3-dimethyl-5-(methylsulfonyl)-)
• 640-57-3(p-Methyldiphenyl Sulfone)
• 10355-06-3(1-Methyl-3-(methylsulfonyl)benzene)
• 3185-99-7(Methyl p-Tolyl Sulfone)
• 33592-56-2(Benzene,1-(methylsulfonyl)-4-(2-phenylethynyl)-)
• 1774-27-2(Benzene,1-[(4-methylphenyl)sulfonyl]-4-(phenylsulfonyl)-)
• 105135-96-4(2-Propyn-1-ol, 3-[4-(methylsulfonyl)phenyl]-)
• 139092-19-6(Benzene, 1-(methylsulfonyl)-4-[[4-(methylthio)phenyl]ethynyl]-)