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Bicycloalkane Building Blocks as Benzene Bioisosters
In recent years, there has been active research aimed at breaking the planarity of pharmacologically active molecules to improve their solubility and in vivo behavior. This approach involves replacing the benzene ring with bioisosteres. For example, bicyclo[1.1.1]pentane building blocks suitable for terminal substitution (1, 2) and para-disubstituted benzene bioisosters (3, 4, 5, 6, 7, 8) are reported.1) Moreover, bicyclo[2.1.1]hexane building blocks (9, 10, 11, 12, 13)2) and bicyclo[3.1.1]heptane building blocks (14, 15, 16, 17)3) are suitable for meta-disubstituted benzene bioisosters. In addition to building blocks with substituents for common condensation reactions, alkyl trifluoroborates (8, 13) are gaining recognition as useful substrates for introducing alkyl substituents in drug discovery.4)
We offer the custom synthesis of analogues and derivatives, as well as scale-up production of these building blocks.
Related Products
- B5479
- Bicyclo[1.1.1]pentan-1-amine Hydrochloride
- B6619
- Bicyclo[1.1.1]pentane-1-carboxylic Acid
- M3149
- 3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic Acid
- A3655
- Methyl 3-Aminobicyclo[1.1.1]pentane-1-carboxylate Hydrochloride
- B6523
- 1-(Boc-amino)bicyclo[1.1.1]pentan-3-amine
- D6184
- 3-(Boc-amino)bicyclo[1.1.1]pentane-1-carboxylic Acid
- B6522
- Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid
- P3127
- Potassium Trifluoro[3-(methoxycarbonyl)bicyclo[1.1.1]pentan-1-yl]borate
- M3703
- 4-(Methoxycarbonyl)bicyclo[2.1.1]hexane-1-carboxylic Acid
- M3705
- Methyl 4-Aminobicyclo[2.1.1]hexane-1-carboxylate Hydrochloride
- B6609
- 4-(Boc-amino)bicyclo[2.1.1]hexane-1-carboxylic Acid
- B6610
- tert-Butyl (4-Aminobicyclo[2.1.1]hexan-1-yl)carbamate
- P3128
- Potassium Trifluoro[4-(methoxycarbonyl)bicyclo[2.1.1]hexan-1-yl]borate
- M3701
- 5-(Methoxycarbonyl)bicyclo[3.1.1]heptane-1-carboxylic Acid
- M3751
- Methyl 5-Aminobicyclo[3.1.1]heptane-1-carboxylate
- B6607
- 5-(Boc-amino)bicyclo[3.1.1]heptane-1-carboxylic Acid
- B6608
- 5-(Boc-amino)bicyclo[3.1.1]heptane-1-amine
Related Product Category Pages
References
- 1) Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug Design
- 2) Saturated bioisosteres of benzene: where to go next?
- 3) Practical and Facile Access to Bicyclo[3.1.1]heptanes: Potent Bioisosteres of meta-Substituted Benzenes
- 4) Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp2)−C(sp3) Cross-Coupling Methods by Library Synthesis
