Abstract
The pentafluorosulfane (SF5) group, as a more electronegative bioisostere than the trifluoromethyl (CF3) group, has been gaining greater attention and increasingly reported usage in medicinal chemistry. Ostarine is the selective androgen receptor modulators (SARMs) containing a CF3 group in clinical trial III. In this study, 21 ostarine derivatives for replacing the CF3 group with SF5 substituents were synthesized. Some SF5-derivatives showed androgen receptor (AR) agonistic activities in vitro. The results pointed to the potential of using this scaffold to develop new AR agonists.
Highlights
Fluorine has been used widely in drug design and development, and 20–25% of pharmaceuticals contain a fluorine atom at present [1]
The pentafluorosulfanyl (SF5 ) group, a bioisostere of the CF3 group, has been gaining greater attention and increasingly reported usage in medicinal chemistry according to the literature [3,4,5]
Meta-SF5 derivativesof 12a–g and 13a–g were displacement prepared, asof bromide illustrated in compound using copper cyanide, leading to the formation of
Summary
Fluorine has been used widely in drug design and development, and 20–25% of pharmaceuticals contain a fluorine atom at present [1]. It is known that the existence of fluorine can influence electrostatic interactions and hydrogen bonding of a ligand [2]. The introduction of fluorine into a compound can change its lipophilicity, pKa, and metabolic stability [1]. Direct fluorination and addition of fluorinated functional groups are common methods to incorporate fluorine. The most common example of functional groups is trifluoromethyl (CF3 ). The pentafluorosulfanyl (SF5 ) group, a bioisostere of the CF3 group, has been gaining greater attention and increasingly reported usage in medicinal chemistry according to the literature [3,4,5]
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