Aminoglycoside type derivative and preparing method and application thereof
A technology of aminoglycosides and derivatives, applied in sugar derivatives, pharmaceutical formulations, medical preparations containing active ingredients, etc.
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Embodiment 1
[0077] (1) The preparation method of etimicin C6' amino-substituted derivatives is as follows:
[0078] 1. Preparation of Compound II (6'-pNZ-etimicin):
[0079]
[0080] Steps: Dissolve 14.01 g of etimicin in 150 mL of methanol, add 6.03 g of diisopropylethylamine, and stir at room temperature for 5 minutes; then dissolve 10.97 g of HONB-pNZ in 150 mL of THF, and add dropwise to the reaction system at room temperature After the dropwise addition was completed, the mixture was stirred overnight at room temperature; then, the solvent was evaporated under reduced pressure and separated by silica gel column chromatography; Compound II was obtained as a white solid with a mass of 7.48 g and a yield of 38.7%. 1 H NMR (600MHz, CDCl 3 ):δ1.03(m,1H),1.10(t,3H),1.12(s,3H),1.38(m,1H),1.65(m,2H),1.74(m,1H),2.17(d, 1H),2.45(d,1H),2.52(m,1H),2.56(s,3H),2.61(m,1H),2.67(m,2H),2.80(m,1H),2.86(m,2H ),3.05(m,2H),3.14(t,1H),3.25(t,1H),3.38(m,1H),3.45(s,2H),3.49(m,1H),3.54(m,1H) ,3.82(d,1H...
Embodiment 2
[0109] (2) The preparation method of etimicin C2' and C6' amino-substituted derivatives is as follows:
[0110] 1. Preparation of compound III (2'-6'-double pNZ-etimicin):
[0111]
[0112] Steps: Dissolve 5.10 g of etimicin in 150 mL of methanol, add 2.14 g of DIPEA, stir at room temperature for 5 minutes, then dissolve 3.81 g of HONB-pNZ in 50 mL of THF, and add dropwise to the reaction system at room temperature; After completion, the mixture was stirred overnight at room temperature, and the solvent was evaporated under reduced pressure, followed by silica gel column chromatography to obtain compound III; it was a white solid with a mass of 2.84 g and a yield of 31.9%. 1 H NMR (600MHz, CDCl 3):δ0.99(m,1H),1.11(s,3H),1.13(t,3H),1.48(m,1H),1.69(m,2H),1.96(m,1H),2.18(d, 1H),2.42(d,1H),2.53(m,1H),2.60(s,3H),2.61(m,1H),2.71(m,1H),2.85(m,1H),2.89(m,2H ),3.11(m,2H),3.22(t,2H),3.27(t,2H),3.38(m,1H),3.42(d,1H),3.45(s,2H),3.50(m,1H) ,3.54(m,1H),3.75(m,2H),3.99(m,1H),4.89(d,2H...
experiment Embodiment 1
[0134] Experimental Example 1: In Vitro Antibacterial Activity Experiment
[0135] 1. Experimental materials: amikacin, micronomycin, etimicin, compounds ET-Alkyl-TM-1-a, ET-Alkyl-TM-1-b, ET-Acyl-TM-1-a , ET-Alkyl-TM-4-a and ET-Alkyl-TM-4-b. (Compounds 1, 2, 3, 4 and 5 are numbered in Table 1 below).
[0136] Table 1
[0137]
[0138]
[0139] 2. Bacterial strains: All the strains are clinical pathogenic bacteria collected from Sichuan and Beijing by the Sichuan Antibiotic Industry Research Institute of Chengdu University in 2012. 4 strains of Staphylococcus aureus, respectively named Staphylococcus aureus 12-1, Staphylococcus aureus 12-2, Staphylococcus aureus 12-3, Staphylococcus aureus 12-4; 12-2, Epiphysis 12-3, Epiphysis 12-4; 2 strains of Streptococcus, named Streptococcus 12-1, Streptococcus 12-2; 3 strains of Escherichia coli, named Escherichia coli 12-1, Escherichia coli 12-2, Escherichia coli 12-3; 4 strains of Klebsiella pneumoniae, respectively named pneu...
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