(20S)-camptothecin derivatives and application thereof
A technology of camptothecin and its derivatives, applied in the field of pesticides, can solve problems such as great influence on the natural control ability of natural enemies, threats to human health, and destruction of ecological balance, and achieve excellent contact activity
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Embodiment 1
[0066] Embodiment 1 camptothecin-20 (S)-O-2,2,3, the synthesis of 3-tetramethylcyclopropanyl carboxylate (a)
[0067] Describe the synthetic route of camptothecin-20(S)-O-2,2,3,3-tetramethylcyclopropanyl carboxylate (a) in detail below: add camptothecin (0.348g, 1mmol) and 4-dimethylaminopyridine (DMAP) (0.742g, 6mmol), pump out the air and replace it with N 2 Finally, 40 mL of dichloromethane and 2,2,3,3-tetramethylcyclopropanecarboxylic acid chloride (0.963 g, 6 mmol) were added, and the mixture was refluxed for 20 h under nitrogen protection. Add 80 mL of dichloromethane after the reaction, and then wash with 0.1 mol / L HCl. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated, and the solid was separated and purified by column chromatography (dichloromethane / methanol / petroleum ether=80 / 1 / 20), and finally 0.21 g of a light yellow solid was obtained. Yield 44.5%. 1 H NMR (DMSO-d 6 ,300MHz)δ0.94(6H,t,J=7.4Hz,H-18,CH 3 ),1.14(3H,s,CH 3 ),1....
Embodiment 2
[0069] Example 2 Synthesis of camptothecin-20 (S)-O-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanyl carboxylate (b)
[0070] The synthetic route of camptothecin-20(S)-O-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanyl carboxylate (b) is similar to a, and the column chromatography develops The agent is dichloromethane / methanol / petroleum ether=80 / 0.5 / 20), and finally 0.25 g of a light yellow solid was obtained, with a yield of 46.4%. 1 H NMR (DMSO-d 6 ,300MHz)δ0.96(3H,t,J=7.1Hz,H-18),1.12(3H,s,CH 3 ),1.20(3H,s,CH 3 ),1.31(1H,s,CHCOO),2.12(1H,s,CHCHCCl 2 ),2.21(2H,m,H-19),5.29(2H,s,H-5),5.49(2H,s,H-17),6.13(1H,m,CHCCl 2 ),6.99(1H,s,H-14),7.74(1H,t,J=7.0Hz,H-10),7.87(1H,t,H-11),8.13(each1H,t,J=7.5Hz ,H-12,H-7),8.67(1H,s,H-9); 13 C NMR (DMSO-d 6 ,75MHz)δ7.8(CH 3 ,C-18),20.1(CH 3 ,CH 3 ),20.2(CH 3 ,CH 3 ),21.9(C,C(CH 3 ) 2 ),22.0(CH,CHCHCCl 2 ), 30.2 (CH 2 ,C-19),33.0(C,CHCOO),50.5(CH 2 ,C-5),56.4(CH 2 ,C-17),76.3(C,C-20),94.8(CH,C-14),118.9(C,C-16),119.9(C,CHCCl 2...
Embodiment 3
[0072] Example 3 Camptothecin-20 (S)-O-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropanyl carboxylate (c) synthesis
[0073] The synthetic route of camptothecin-20(S)-O-3-(2-chloro-2-trifluoromethylvinyl)-2,2-dimethylcyclopropanyl carboxylate (c) is similar to a, The developing solvent for column chromatography was ethyl acetate / petroleum ether=3 / 2, and finally 0.333 g of light yellow solid was obtained, with a yield of 58.1%. 1 H NMR (DMSO-d 6 ,300MHz)δ0.94(3H,t,J=7.4Hz,H-18),1.20(3H,s,CH 3 ),1.34(3H,s,CH 3 ),2.18(2H,m,H-19),2.37(1H,d,J=8.5Hz,CHCOO),2.56(1H,d,J=8.4Hz,CHCHC(CF 3 )Cl),5.28(2H,s,H-5),5.49(2H,s,H-17),6.59(1H,d,J=9.2Hz,CHC(CF 3)Cl),6.98(1H,s,H-14),7.73(1H,dd,J=8.0,1.0Hz,H-10),7.86(1H,t,J=1.4Hz,H-11),8.13 (each1H,t,J=8.1Hz,H-7,H-12),8.67(1H,s,H-9); 13 C NMR (CDCl 3 ,75MHz)δ7.2(CH 3 ,C-18),14.5(CH 3 ,CH 3 ), 18.8 (CH 3 ,CH 3 ),28.0(C,C(CH 3 ) 2 ),31.2(CH,CHCHC(CF 3 ) Cl), 31.6 (CH 2 ,C-19),32.0(CH,CHCOO),49.6(CH 2 ,C-5),66.8(CH 2 ,C-17),...
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