Design, Synthesis of a Novel Phosphatase 1B Inhibitor and the Evaluation of Its Biology Activity and Toxicity in vitro
- Corresponding author: Zhou Honggang, honggang.zhou@nankai.edu.cn
Citation: Lu Chenga, Liu Xiang, Tang Yanting, Xu Yongxue, Zhong Weilong, Sun Taoa, Zhou Honggang. Design, Synthesis of a Novel Phosphatase 1B Inhibitor and the Evaluation of Its Biology Activity and Toxicity in vitro[J]. Acta Chimica Sinica, ;2015, 74(2): 155-164. doi: 10.6023/A15090597
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Reagents and conditions: (a) methyl-2,6-dihydroxybenzoate,PPh3,DIAD,THF,0 oC to r.t.,65%; (b) benzyl bromide,K2CO3,DMF,r.t.,99%; (c) 2 mol•L-1 HCl in dioxane,r.t.,92%.
Reagents and conditions: (a) N-(tert-butoxycarbonyl)-L-iodoalanine methyl ester,I2,Zn,P(o-Tol)3,Pd(OAc)2,DMF,50 ℃,70%; (b) NaOH,MeOH/dioxane/H2O (V:V:V = 1:1:1),0 ℃,81%.
Reagents and conditons: (a) 27,TBTU,Et3N,HOBt,DMF,r.t.,91%; (b) (S)-tert-butanesulfinamide,titanium tetraisopropanolate,toluene,60 ℃,97%; (c) tert-butoxycarbonyloxyacetic acid methyl ester,LiHMDS,N2,THF,-78 ℃,66%; (d) 4 mol•L-1 HCl,MeOH,dioxane,H2O,r.t.,47%; (e) phenylacetyl chloride,DIEA,THF,r.t.,60%; (f) 6 mol•L-1 HCl,MeOH,r.t.,81%; (g) Boc2O,Et3N,CH2Cl2,r.t.,55%; (h) Dess-Martin periodinane,CH2Cl2,r.t.,70%.
ΔΔP<0.01 vs control group; **P<0.01 vs model (IR) group,PIOG: Pioglitazone positive control group
(a) The morphology of zebrafish treated with compound 20 at the concentration of 50 μmol•L-1,(b) the morphology of zebrafish treated with compound 20 at the concentration of 500 μmol/L,(c) the morphology of control group and (d) heartbeat data comparison chart of three zebrafish groups