Synthesis and biological evaluation of 4-(piperid-3-yl)amino substituted 6-pyridylquinazolines as potent PI3Kδ inhibitors

Bioorganic & Medicinal Chemistry
2019.0

Abstract

PI3Kδ is an intriguing target for developing anti-cancer agent. In this study, a new series of 4-(piperid-3-yl)amino substituted 6-pyridylquinazoline derivatives were synthesized. After biological evaluation, compounds A5 and A8 were identified as potent PI3Kδ inhibitors, with IC<sub>50</sub> values of 1.3 and 0.7 nM, respectively, which are equivalent to or better than idelalisib (IC<sub>50</sub> = 1.2 nM). Further PI3K isoforms selectivity evaluation showed that compound A5 afforded excellent PI3Kδ selectivity over PI3Kα, PI3Kβ and PI3Kγ. A8 exhibited superior PI3Kδ/γ selectivity over PI3Kα and PI3Kβ. Moreover, compounds A5 and A8 selectively exhibited anti-proliferation against SU-DHL-6 in vitro with IC<sub>50</sub> values of 0.16 and 0.12 μM. Western blot analysis indicated that A8 could attenuate the AKT<sup>S473</sup> phosphorylation. Molecular docking study suggested that A8 formed three key H-bonds action with PI3Kδ, which may account for its potent inhibition of PI3Kδ. These findings indicate that 4-(piperid-3-yl)amino substituted 6-pyridylquinazoline derivatives were potent PI3Kδ inhibitors with distinctive PI3K-isoforms and anti-proliferation profiles.

Knowledge Graph

Similar Paper

Synthesis and biological evaluation of 4-(piperid-3-yl)amino substituted 6-pyridylquinazolines as potent PI3Kδ inhibitors
Bioorganic &amp; Medicinal Chemistry 2019.0
Novel 6-aryl substituted 4-pyrrolidineaminoquinazoline derivatives as potent phosphoinositide 3-kinase delta (PI3Kδ) inhibitors
Bioorganic &amp; Medicinal Chemistry 2018.0
Conformationally restricted quinazolone derivatives as PI3Kδ-selective inhibitors: the design, synthesis and biological evaluation
MedChemComm 2019.0
Design and synthesis of novel 6-aryl substituted 4-anilinequinazoline derivatives as potential PI3Kδ inhibitors
Bioorganic &amp; Medicinal Chemistry Letters 2017.0
SAR study of 5-alkynyl substituted quinazolin-4(3H)-ones as phosphoinositide 3-kinase delta (PI3Kδ) inhibitors
European Journal of Medicinal Chemistry 2017.0
Synthesis and biological evaluation of novel purinyl quinazolinone derivatives as PI3Kδ-specific inhibitors for the treatment of hematologic malignancies
Bioorganic &amp; Medicinal Chemistry 2021.0
Synthesis and SAR study of potent and selective PI3Kδ inhibitors
Bioorganic &amp; Medicinal Chemistry Letters 2015.0
Discovery of novel quinazolinone derivatives as high potent and selective PI3Kδ and PI3Kδ/γ inhibitors
European Journal of Medicinal Chemistry 2018.0
Design, synthesis and structure-activity relationship study of piperazinone-containing thieno[3,2-d]pyrimidine derivatives as new PI3Kδ inhibitors
Bioorganic &amp; Medicinal Chemistry Letters 2020.0
Design, synthesis and in vitro biological evaluation of 2-aminopyridine derivatives as novel PI3Kδ inhibitors for hematological cancer
Bioorganic &amp; Medicinal Chemistry Letters 2023.0