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Discovery of new Lenalidomide derivatives as potent and selective GSPT1 degraders 1 1 Introduction 1 2 Molecular design 2 3 Chemistry 2 4 Results and discussion 2 4.1 Structure-activity relationship (SAR) study based on compound 9a 2 4.2 Compound 4q degraded GSPT1 in a dose- and time-dependent manner 3 4.3 Compound 4q induced GSPT1 degradation through the UPS 4 4.4 Global proteomic profiling of compound 9q 4 4.5 Compound 9q potently inhibited leukemia cancer cell proliferation 5 4.6 Compound 9q induced G0/G1 phase arrest and apoptosis in U937 cells 5 4.7 Pharmacokinetic (PK) evaluation of compound 9q in SD rats 6 5 Conclusions 6 6 Experimental section 6 6.1 General methods for chemistry 6 6.1.1 Tert-butyl (E)-3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)acrylate (11a) 6 6.1.2 Tert-butyl 3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)propanoate (12a) 6 6.1.3 N-(3-chloro-4-methylphenyl)-3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)propanamide (9a) 7 6.1.3.1 N-(3-chloro-4-methylphenyl)-3-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoin-dolin-5-yl)propanamide(9b) 7 6.1.3.2 N-(3-chloro-4-methylphenyl)-3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindo-lin-4-yl)propenamide (9c) 7

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UND

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nonfiction