Analog of actinomycin D
A technology of actinomycin and analogs, applied in the field of new compounds, can solve problems such as high toxicity, and achieve the effect of reducing toxicity and improving anti-tumor activity
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Embodiment 1
[0022] Example 1: [D-Phe 2 , D-MeVal 5 ] 2 Synthesis of AMD
[0023]I Dissolve 0.63 g (2.26 mmol) of the compound N-benzyloxycarbonyl-N-methylglycine tert-butyl ester in 6 ml of anhydrous methanol (MeOH), add 80 mg of 10% Pd / C, stir for 2 hours after hydrogenation, filter and concentrate , add Z-Pro 0.535g (2.15mmol) to the residue, dissolve with dry dichloromethane (DCM) and cool to -10°C, add 0.44g (2.15mmol) of DCC in dichloromethane solution, at -10°C After reacting for 2 hours, react overnight at room temperature. The DCU generated by the reaction was filtered off, the filtrate was concentrated, and the residue was dissolved in ethyl acetate (EtOAc), followed by 10% citric acid aqueous solution, 10% sodium bicarbonate (NaHCO 3 ) aqueous solution, washed with saturated sodium chloride (NaCl) aqueous solution, and washed with anhydrous sodium sulfate (NaCl) 2 SO 4 )dry. After filtration, the solvent was evaporated under reduced pressure, and the crude product was sub...
Embodiment 2
[0030] Embodiment 2: [D-Phe 2 , D-MePhe 5 ] 2 Synthesis of AMD
[0031] Reaction steps I to III and synthetic process are identical with embodiment 1 in the present embodiment;
[0032] IV Take the compound N-benzyloxycarbonyl-threonyl-D-phenylalanyl-prolyl-N-methylglycine tert-butyl ester 423mg (0.68mmol) and Boc-D-Me Val 264.8mmg (0.95mmol), Dissolve in dry DCM and cool to -10°C, add 195.5 mg (0.95 mmol) of DCC in DCM, and 82.7 mg (0.68 mmol) of DMAP, react overnight at room temperature, filter out the DCU generated by the reaction, concentrate the filtrate, and dissolve the residue in EtOAc, sequentially with 10% aqueous citric acid, 10% NaHCO 3 solution, washed with saturated NaCl, and washed with anhydrous NaCl 2 SO 4 dry. Filtration, the solvent was evaporated under reduced pressure, and the crude product was subjected to silica gel column chromatography (EtOAc:PE 2:1) to obtain white powder N-tert-butoxycarbonyl-D-N-methylphenylalanyl-N-benzyloxycarbonyl-threonin...
Embodiment 3
[0036] Example 3: [D-MeVal 2 ] 2 Synthesis of AMD
[0037] Reaction steps 1 and synthetic process are identical with embodiment 1 in the present embodiment;
[0038] II Dissolve 1.90 g (5.05 mmol) of the compound N-benzyloxycarbonyl-prolyl-N-methylglycine tert-butyl ester in 25 ml of anhydrous MeOH, add 212 mg of 10% Pd / C, hydrogenate for 2 hours, filter, concentrate, Add 1.47g (5.56mmol) of Z-D-MeVal to the residue, dissolve in dry DCM and cool to -10°C, add 1.15g (5.56mmol) of DCC in DCM, react at -10°C for 2 hours, then react overnight at room temperature, The DCU generated by the reaction was filtered off, the filtrate was concentrated, and the residue was dissolved in EtOAc, followed by 10% citric acid aqueous solution, 10% NaHCO 3 solution, washed with saturated NaCl, and washed with anhydrous NaCl 2 SO 4 dry. Filtration, the solvent was evaporated under reduced pressure, and the crude product was subjected to silica gel column chromatography (EtOAc:PE 2:1) to obta...
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