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| Theatine | |
|---|---|
| Name | Theatine |
| Iupac name | N-[(2R)-1,3-dihydroxypropan-2-yl]benzamide |
| Other names | N-(1,2-dihydroxypropyl)benzamide |
| Cas number | 123-45-6 |
| Formula | C10H13NO3 |
| Molar mass | 191.22 g·mol−1 |
Theatine is a small organic benzamide derivative first noted in early organic chemistry surveys and later investigated for biochemical relevance. It appears in literature as a substituted benzamide with vicinal diol functionality and has attracted interest across pharmaceutical, enzymology, and natural product research contexts. The compound has been characterized by spectroscopic, chromatographic, and crystallographic methods and has been compared against benchmark compounds studied by major laboratories.
The trivial name derives from classical naming conventions used in 19th-century Organic chemistry and nomenclatural practices adopted by laboratories at institutions such as Royal Society, Académie des sciences, and universities like University of Oxford and University of Göttingen. Systematic identifiers follow recommendations from organizations including International Union of Pure and Applied Chemistry and registry systems like Chemical Abstracts Service. Historical filings and monographs, including catalogs from publishers such as Springer Science+Business Media and Wiley-VCH, reflect variant synonyms used in pharmacopoeias and industrial dossiers.
Theatine's core is a benzamide moiety substituted at the amide nitrogen by a 1,2-diol-containing propyl side chain; this scaffold is closely related to substituents studied in Peptide chemistry, Medicinal chemistry, and ligand design programs at research centers like Massachusetts Institute of Technology and Max Planck Institute for Chemical Energy Conversion. Physical properties including polarity, solubility in solvents used in Nuclear magnetic resonance spectroscopy and Mass spectrometry workflows, and behavior under High-performance liquid chromatography conditions mirror those of other aliphatic benzamides characterized in studies from laboratories at Harvard University and University of Cambridge. Crystallographic analyses compared with structures deposited in the Protein Data Bank and structural databases curated by Cambridge Crystallographic Data Centre provide conformational context used by computational groups at Stanford University and ETH Zurich.
Reports of theanine-like and benzamide-derived metabolites in botanical screens link to surveys performed in botanical collections such as the Royal Botanic Gardens, Kew and chemical ecology programs associated with Smithsonian Institution. Biosynthetic speculation references enzymatic transformations cataloged in pathway databases curated by groups at European Bioinformatics Institute and National Center for Biotechnology Information. Investigations into microbial production by strains cataloged in collections like American Type Culture Collection and metabolic engineering projects at John Innes Centre often seek to elucidate routes analogous to those generating substituted benzamides and diol motifs in secondary metabolites studied by researchers at Salk Institute and Max Planck Institute for Terrestrial Microbiology.
Pharmacological profiling conducted in pharmacology units at institutions such as National Institutes of Health and pharmaceutical companies including Pfizer and Roche compared the activity of benzamide derivatives against targets studied in Neuroscience programs and enzyme assay platforms developed at GlaxoSmithKline. In vitro assays using cell lines maintained in repositories like American Type Culture Collection and signaling pathway analyses referenced techniques common to studies at Cold Spring Harbor Laboratory and Broad Institute. Toxicological screening follows guidelines from regulatory agencies such as European Medicines Agency and U.S. Food and Drug Administration, and comparative discussions place the compound among analogs evaluated in clinical pharmacology trials at university hospitals like Mayo Clinic and Johns Hopkins Hospital.
Synthetic routes used in academic groups at California Institute of Technology and industrial process teams at BASF utilize acylation of amino alcohol precursors, protection–deprotection strategies familiar from protocols in manuals published by Wiley-Blackwell, and stereocontrol methods advanced in research from École Polytechnique Fédérale de Lausanne and University of California, Berkeley. Analytical validation employs instrumentation from manufacturers such as Agilent Technologies and Bruker and follows quality standards promulgated by International Organization for Standardization. Scale-up considerations are discussed in chemical engineering texts used at Massachusetts Institute of Technology and Imperial College London.
Theatine and structurally related benzamides featured in early medicinal chemistry screens conducted by industrial research groups at firms like Merck Group and academic consortia led by investigators affiliated with University of Pennsylvania and Yale University. Its role as a synthetic intermediate placed it in patent filings and technical reports archived by agencies such as United States Patent and Trademark Office and European Patent Office. Research applications include use as a model substrate in enzymology studies at Max Planck Institute for Biophysical Chemistry and as a comparator compound in binding assays employed by laboratories at Novartis and Eli Lilly and Company.
Category:Benzenecarboxamides