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Small Ring Building Blocks for Medicinal Chemistry
No.180(April 2019)
Cross-coupling reactions have become ubiquitous in synthesis and are essential in enabling the expansion of building block libraries, which has notably had a positive impact on the synthesis of pharmaceuticals with a high sp2 carbon ratio. Unfortunately, reviews of clinical trial data has shown drug candidates with high planarity were more likely to fail.1) It was speculated that the planarity of compounds caused unpredictable and undesirable bioavailability and toxicity owing to their insolubility. This pitfall has demonstrated the importance of sp3 character in drug candidates and its needed emphasis. Spiro type building blocks comprised of an oxetane and azetidine (1,2)2,3) are bioisosteres of morpholine and piperazine respectively. The related bicyclo[1.1.1]pentane or cubane (3,4,5)4,5) are bioisosteres of benzene rings. The introduction of these unique functionalities from selected building blocks are expected to assist in the introduce more sp3 carbon character to drug candidates while still retaining paralleled biological properties to their bioisosteres, lending to improved solubility and increase 3-dimensionality.
References
- 1)Escape from flatland: Increasing saturation as an approach to improving clinical success
- 2)Spirocyclic oxetanes: Synthesis and properties
- 3)2,6-Diazaspiro[3.3]heptanes: Synthesis and application in Pd-catalyzed aryl amination reactions
- 4)Strain-release heteroatom functionalization: Development, scope, and stereospecificity
- 5)Cubanes in medicinal chemistry
- 6)Discovery of (3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone (AZD1979), a melanin concentrating hormone receptor 1 (MCHr1) antagonist with favorable physicochemical properties
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