Bioorganic and Medicinal Chemistry Letters p. 144 - 148 (2012)
Update date:2022-08-04
Topics:
Kurata, Haruto
Kusumi, Kensuke
Otsuki, Kazuhiro
Suzuki, Ryo
Kurono, Masakuni
Tokuda, Natsuko
Takada, Yuka
Shioya, Hiroki
Mizuno, Hirotaka
Komiya, Takaki
Ono, Takeji
Hagiya, Hiroshi
Minami, Masashi
Nakade, Shinji
Habashita, Hiromu
Structure-activity relationship (SAR) of sphingosine-1-phosphate receptor agonists with a dihydronaphthalene scaffold was investigated. Compound 1 was modified to improve S1P1 agonistic activity and in vivo peripheral lymphocyte lowering (PLL) activity without impairing selectivity over S1P 3 agonistic activity. A detailed SAR study of the terminal lipophilic part revealed that the introduction of substituents on the propylene linker and the terminal benzene ring influences in vitro and PLL activities. Compound 6n bearing a (S)-methyl group at the 2-position on the propylene linker and chlorine at the para-position on the terminal benzene ring showed potent hS1P1 agonistic activity with excellent selectivity over hS1P 3 and in vivo PLL activity in mice.
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