The 3F Library: Fluorinated Fsp³‐Rich Fragments for Expeditious ¹⁹F NMR Based Screening

Abstract

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Transferring Substituents from Alkynes to Furans and Pyrroles through Heteronorbornadienes as Intermediates: Synthesis of β-Substituted Pyrroles/Furans

“…Most (hetero)norbornadienes were prepared by DA cycloaddition between furan/ N -Boc-pyrrole and activated alkynes (commercial or synthetically achievable) as it was reported in previous works . Bicyclic bromovinyl phosphonates 9j – 9m were prepared here for the first time.…”

“…Most (hetero)norbornadienes were prepared by DA cycloaddition between furan/ N -Boc-pyrrole and activated alkynes (commercial or synthetically achievable) as it was reported in previous works. 13 Bicyclic bromovinyl phosphonates 9j – 9m were prepared here for the first time. With this (hetero)norbornadienic substrates in hand, we decided to explore the tandem iEDDA/rDA/rDA by reaction with DPTz as it is shown in Scheme 2 (Procedure A).…”

Identification of 5-HT2 Serotonin Receptor Modulators through the Synthesis of a Diverse, Tropane- and Quinuclidine-alkaloid-Inspired Compound Library

“…30,31 Furthermore, the average fraction of sp 3 hybridized carbons (Fsp 3 = 0.48) was the same as the average for approved drugs (Supporting Information Figure S3B). 32 Together, these data suggest that the compounds are likely to display drug-like properties.…”

Library Design Strategies To Accelerate Fragment‐Based Drug Discovery

“…[32][33][34] Recently, Clausena nd co-workersp ublished the synthesis and 19 FNMR spectroscopic screening of their fluorinated Fsp 3rich fragment (3F) library;t his was the first example of as ynthetic library fully designed for this purpose (Figure 2). [35] With ah igh degree of three-dimensionality,t he 3F library was designed to address the need to improve the limited shape diversity of many fragment collections, while enabling efficient screening by 19 FNMR spectroscopy.F urthermore, the library also exhibitedo ther desirable properties compared with those of commercial collections, including al ow average Alog P of 0.8 to ensure sufficient aqueous solubility. As ap roof-of-concept, the 3F library wass creened against four disease-related targets to provideatotal of 30 hits (hit rates ranging from 3t o 11 %).…”