Bicycloalkane Building Blocks as Benzene Ring Bioisosteres

Bicycloalkane building blocks from TCI, including bicyclo[1.1.1]pentane derivatives (for example, codes M3149, A3655, D6184), are used to replace the benzene ring in pharmacologically active molecules. This approach breaks molecular planarity, aiming to improve solubility and pharmacokinetic behavior.¹) Bicyclo[1.1.1]pentane building blocks are suitable for terminal substitution and serve as para-disubstituted benzene bioisosteres.¹) For meta-disubstituted benzene bioisosteres, bicyclo[2.1.1]hexane and bicyclo[3.1.1]heptane building blocks are available, including codes M3703, M3705, B6609, M3701, M3751, and B6607.²)³) TCI also offers custom synthesis of analogues and derivatives, as well as scale-up production of these building blocks.

Related products

• TCI M3149 83249-10-9 3-(Methoxycarbonyl)bicyclo[111]pentane-1-carboxylic Acid
• TCI D6184 303752-38-7 3-[(tert-Butoxycarbonyl)amino]bicyclo[1.1.1]pentane-1-carboxylic Acid
• TCI B6523 1638767-25-5 tert-Butyl (3-Aminobicyclo[1.1.1]pentan-1-yl)carbamate
• TCI B6522 56842-95-6 Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid
• TCI B5479 22287-35-0 Bicyclo[1.1.1]pentan-1-amine Hydrochloride
• TCI B6619 22287-28-1 Bicyclo[1.1.1]pentane-1-carboxylic Acid
• TCI M3703 141046-52-8 4-(Methoxycarbonyl)bicyclo[2.1.1]hexane-1-carboxylic Acid
• TCI B6609 1050886-56-0 4-[(tert-Butoxycarbonyl)amino]bicyclo[2.1.1]hexane-1-carboxylic Acid

References

1. Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug Design. N. A. Meanwell et al., J. Med. Chem. 2021, 64, 14046. doi:10.1021/acs.jmedchem.1c01215
2. Saturated bioisosteres of benzene: where to go next?. P. K. Mykhailiuk, Org. Biomol. Chem. 2019, 17, 2839. doi:10.1039/C8OB02812E
3. Practical and Facile Access to Bicyclo[3.1.1]heptanes: Potent Bioisosteres of meta-Substituted Benzenes. M. Uchiyama et al., J. Am. Chem. Soc. 2022, 144, 21848. doi:10.1021/jacs.2c09733

Download TCI brochure Bicycloalkane Building Blocks ― Benzene Bioisosteres ― (PDF)

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Source

• TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20240624
• TCI product page B5479: tcichemicals.com/ID/en/p/B5479
• TCI product page B6522: tcichemicals.com/ID/en/p/B6522
• TCI product page B6523: tcichemicals.com/ID/en/p/B6523
• TCI product page B6607: tcichemicals.com/ID/en/p/B6607
• TCI product page B6608: tcichemicals.com/ID/en/p/B6608
• TCI product page B6609: tcichemicals.com/ID/en/p/B6609
• TCI product page B6610: tcichemicals.com/ID/en/p/B6610
• TCI product page B6619: tcichemicals.com/ID/en/p/B6619
• TCI product page D6184: tcichemicals.com/ID/en/p/D6184
• TCI product page M3149: tcichemicals.com/ID/en/p/M3149
• TCI product page M3701: tcichemicals.com/ID/en/p/M3701
• TCI product page M3703: tcichemicals.com/ID/en/p/M3703

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