[1-(4-Methyl-benzylsulfanyl)-cyclohexyl]-acetic acid is a cyclohexylacetic acid derivative bearing a thioether substituent at the 1-position, classifying it as a non-proteinogenic, structurally modified amino-acid-like compound with a carboxylic acid and a side-chain sulfur functionality. The molecule contains a free carboxyl group and an acetic acid methylene linker to the cyclohexyl ring, with the thioether side chain featuring a benzyl sulfanyl group substituted by a methyl substituent on the aromatic ring, providing a chemically stable sulfur-based handle for further derivatization or conjugation chemistry. As a free amino-acid-like building block, it can be used in structure-activity studies, chemical biology labeling strategies, or the preparation of more complex thioether-containing amino acid and peptide-related intermediates where the non-natural thioether motif is incorporated to modulate physicochemical properties or introduce a functional group for downstream coupling.
CAT No: CP27550
CAS No:87242-91-9
Synonyms/Alias:87242-91-9;BETA-(4-METHYL-BENZYLSULFANYL)-BETA,BETA-CYCLOPENTAMETHYLENE-PROPIONICACID;AC1ODVAA;C16H22O2S;2-[1-[(4-methylphenyl)methylsulfanyl]cyclohexyl]aceticAcid;ZINC2571891;6172AH;KM2496;AKOS025404121;AK186750;OR124791;Beta-(4-methylbenzylsulfanyl)-beta,beta-cyclopentamethylene-propionicacid
[1-(4-Methyl-benzylsulfanyl)-cyclohexyl]-acetic acid is a sulfur-containing, cyclohexyl-substituted amino acid derivative featuring a thioether side chain and a carboxylic acid suitable for downstream organic synthesis and medicinal chemistry workflows. Its non-proteinogenic structure and conformationally constrained cyclohexyl framework make it a useful building block for preparing peptidomimetic motifs, enzyme-inhibitor scaffolds, and other stereochemically defined analogs where a thioether-bearing side chain is required. The free acid functionality supports coupling chemistry and incorporation into larger synthetic sequences, while the thioether group provides a chemically stable sulfur handle for structure-activity relationship studies.
1. Peptidomimetic Building Block
[1-(4-Methyl-benzylsulfanyl)-cyclohexyl]-acetic acid is used as a non-natural amino acid building block in peptidomimetic and constrained ligand design, where a cyclohexyl-based backbone and a thioether-bearing side chain help tune sterics and hydrophobic character. Medicinal chemistry groups incorporate this motif into analog series to probe how sulfur-containing substituents influence binding interactions and overall scaffold conformation. The carboxylic acid enables efficient conversion to coupling-ready derivatives for assembly into larger peptide-like structures, supporting custom synthesis of research-grade analogs for SAR campaigns.
2. Medicinal Chemistry Intermediates
[1-(4-Methyl-benzylsulfanyl)-cyclohexyl]-acetic acid serves as a practical intermediate for medicinal chemistry programs that require a sulfur-functionalized amino acid derivative as part of a larger pharmacophore. Synthetic teams use it to introduce a defined thioether substituent into lead optimization libraries, including analogs where thioether substitution is used to modulate physicochemical properties and interaction patterns without relying on reactive thiols. The conformational constraint from the cyclohexyl ring supports the preparation of structurally consistent series, which is valuable for iterative synthesis and characterization workflows in small-molecule discovery.
3. Thioether-Containing SAR Analog Synthesis
[1-(4-Methyl-benzylsulfanyl)-cyclohexyl]-acetic acid is routinely selected for SAR studies focused on side-chain variation around a thioether substituent. Chemical biology and medicinal chemistry laboratories use it to generate analogs that retain the thioether motif while varying other regions of the molecule, enabling controlled comparison of how sulfur substitution impacts structure-property relationships. The stable thioether functionality provides a chemically robust handle that withstands many standard synthetic and purification conditions used during library synthesis, making it useful for producing consistent, characterization-ready research compounds.
4. Constrained Scaffold Derivatization
[1-(4-Methyl-benzylsulfanyl)-cyclohexyl]-acetic acid is applied in the derivatization of conformationally constrained scaffolds where cyclohexyl substitution is used to control geometry and reduce unwanted flexibility. Researchers incorporate this building block into larger synthetic architectures to create defined spatial presentation of the acetic acid functionality and the thioether side chain, supporting the development of analogs for structure-activity relationship mapping. In custom synthesis workflows, its free acid group supports downstream functional group transformations and coupling steps that feed directly into characterization by NMR, LC-MS, and chromatographic purity assessment.
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