Saturated Bioisosteres for ortho-substituted Benzenes
The fragment of benzene is the most popular ring in bioactive compounds. In fact, more than 500 drugs and agrochemicals are benzene-containing molecules. In 2012, chemists at Pfizer replaced the substituted phenyl fragment in a ɣ-secretase inhibitor Avagacestat with the bicyclo[1.1.1]pentyl skeleton. The obtained analogue showed higher activity, solubility and metabolic stability. Since then, bicyclo[1.1.1]pentanes, bicyclo[2.2.2]octanes and cubanes are used in medicinal chemistry as saturated bioisosteres for para-substituted benzenes. Therefore, here we have designed and synthesized saturated mimetics for ortho-substituted benzenes.
Design
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MedChem Highlights
- Analogues of Piperidine for Drug Design
- SnAP Reagents
- Fluoroalkyl ethers for Drug Design
- N-Nitrosamines
- N-Trifluoromethyl Azoles for Drug Discovery
- Cyclic sulfates and sulfamidates as alkylating reagents
- Saturated Bioisosteres for ortho-substituted Benzenes
- Aliphatic Trifluoroborates (-BF3) for C-C couplings
- Functionalized Vinyl Boronates for C-C couplings
- Unique 3D-shaped Spirocycles
- Water-soluble non-classical benzene mimics
- gem-Difluorinated Amines for Drug Design
- Fluorosulfates and Sulfamoyl Fluorides
- Alkyne-containing Linkers
- Structurally optimized tetrazines for rapid biological labeling
- Building blocks and linkers for PROTAC synthesis
- Heterocyclic Sulfonyl Fluorides
- Silicon-Containing Building Blocks
- Epoxides for Drug Design
- Analogues of CF3-Pyridine for Drug Design
- Piperazine Bioisosteres for Drug Design
- Sugar-like Building Blocks for Drug Design
- Cyclic Sulfonamides for Drug Design
- Morpholine Bioisosteres for Drug Design
- P(O)Me2-containing Building Blocks
- Saturated Bioisosteres of ortho-/meta-substituted Benzenes
- Saturated bioisosteres of para-substituted benzenes
- Sulfonyl fluorides (-SO2F)
- Diazirines
- Oxetane-containing Building Blocks
- SF5-Building Blocks
- Stannanes for coupling reactions
- Sulfoximines for Drug Design
- Heterocyclic scaffolds
- Azide-linkers for Drug Design
- Unnatural Amino Acids
- Cubanes for Medicinal Chemistry
- Benzoxaboroles for Drug Design