Macrolide brefeldin A ester derivative and application thereof
A kind of technology of feldsparin and derivatives, applied in the field of medicine
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Embodiment 1
[0222] 7-O-(3-fluorocinnamic acid) acyl BFA (compound 1a) 4-O-(3-fluorocinnamic acid) acyl BFA (compound 1b)
[0223] 4,7-O-bis(3-fluorocinnamic acid)yl BFA (compound 1c)
[0224]
[0225] Under the protection of nitrogen, BFA (40mg, 1eq), DMAP (1eq) and EDC·HCl (4eq) were dissolved in 8ml of anhydrous DCM, stirred at 40°C for 10 min, and then the DCM solution of 3-fluorocinnamic acid (2eq) was added , continue to react for 2h, after the reaction is detected by TLC, water is added for extraction, the organic phase is concentrated under reduced pressure, the crude extract is separated and purified to obtain white solids 1a, 1b, and 1c, and the yields are 20%, 40%, and 30% in turn.
[0226] Structural Characterization: 1a: 1 H NMR (600 MHz, Chloroform- d ) δ = 7.59 (d, J =16.0, 1H),7.39 – 7.31 (m, 2H), 7.29 (s, 1H), 7.21 (dt, J =9.6, 2.0, 1H), 7.07 (td, J =8.3, 2.5, 1H), 6.39 (d, J =15.9, 1H), 5.93 (dd, J =15.6, 1.9, 1H), 5.73 (ddd, J =15.0, 10.2, 4.6, 1H), 5.32 – 5.1...
Embodiment 2
[0230] 7-O-(2-fluorocinnamic acid) acyl BFA (compound 2a) 4-O-(2-fluorocinnamic acid) acyl BFA (compound 2b)
[0231] 4,7-O-bis(2-fluorocinnamic acid)yl BFA (compound 2c)
[0232]
[0233] Referring to the preparation method of Example 1, white solids 2a, 2b, 2c were obtained. The yields were 20%, 45%, and 30%, respectively.
[0234] Structural Characterization: 2a: 1 H NMR (600 MHz, Chloroform- d ) δ = 7.78 (d, J =16.2, 1H),7.53 (td, J =7.6, 1.7, 1H), 7.39 – 7.32 (m, 2H), 7.16 (td, J =7.5, 1.1, 1H),7.10 (ddd, J =10.8, 8.2, 1.1, 1H), 6.50 (d, J =16.2, 1H), 5.93 (dd, J =15.7,2.0, 1H), 5.73 (ddd, J =15.0, 10.3, 4.6, 1H), 5.31 – 5.22 (m, 2H), 4.86 (dqd, J =12.6, 6.3, 1.7, 1H), 4.15 (dt, J =9.6, 2.5, 1H), 2.47 – 2.26 (m, 3H), 2.06 –1.81 (m, 5H), 1.78 – 1.64 (m, 2H), 1.58 – 1.48 (m, 1H), 1.26 (d, J =6.2, 3H),0.99 – 0.90 (m, 1H). 13 C NMR (150 MHz, Chloroform- d ) Δ = 166.6, 162.3, 160.6,151.6, 137.5, 136.1, 131.9, 131.1, 129.2, 124.6, 121.0, 117.9, 116.4,76.0, 71.9...
Embodiment 3
[0238] 7-O-(4-fluorocinnamic acid) acyl BFA (compound 3a) 4-O-(4-fluorocinnamic acid) acyl BFA (compound 3b)
[0239] 4,7-O-bis(4-fluorocinnamic acid)yl BFA (compound 3c)
[0240]
[0241] Referring to the preparation method of Example 1, white solids 3a, 3b, 3c were obtained. The yields were 20%, 33%, and 43%, respectively.
[0242] Structural characterization: Compound 3a: 1 H NMR (600 MHz, Chloroform- d ) δ = 7.61 (d, J =16.0,1H), 7.54 – 7.48 (m, 2H), 7.36 (dd, J =15.7, 3.1, 1H), 7.10 – 7.04 (m, 2H),6.32 (d, J =16.0, 1H), 5.93 (dd, J =15.6, 1.9, 1H), 5.73 (ddd, J =15.0, 10.2,4.6, 1H), 5.32 – 5.20 (m, 2H), 4.86 (dqd, J =12.5, 6.2, 1.8, 1H), 4.15 (dt, J =9.7, 2.3, 1H), 2.42 (qd, J =9.1, 7.0, 1H), 2.40 – 2.33 (m, 1H), 2.29 (dddd, J =12.9, 7.3, 3.3, 1.5, 1H), 2.02 (dddd, J =10.5, 8.3, 5.0, 2.7, 1H), 1.98 – 1.91(m, 1H), 1.91 – 1.82 (m, 2H), 1.78 – 1.71 (m, 1H), 1.72 – 1.62 (m, 2H), 1.53( dddd, J =14.5, 10.9, 7.3, 2.3, 1H), 1.26 (d, J =6.2, 3H), 0.99 – 0.89 (m, ...
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