New process for synthesizing N-alkanoyl cordycepin serving as cordycepin derivative by one-step method

Abstract

The invention relates to a new process for synthesizing N-alkanoyl cordycepin serving as a cordycepin derivative by a one-step method, and discloses the new process for preparing the N-alkanoyl cordycepin by the one-step method. Compared with the conventional preparation process, the new process has the characteristics of a few synthesis steps, low cost of used raw materials (the cost is only 20 percent of that of the conventional preparation process), high yield (the yield of the conventional preparation process is 40 percent and the yield of the process is 85 percent), light pollution (pyridine is used by the conventional process and acetone or ethyl ether is used by the process) and the like and is more favorable for industrial development of the N-alkanoyl cordycepin.

Description

technical field

[0001] The invention relates to a new synthesis process of N-alkanoyl cordycepin. Background technique

[0002] Since Cunningham et al. isolated cordycepin (Cordycepin) from the culture liquid of Cordyceps militaris (L.) Link in 1951, its various biological activities have gradually been recognized by people, and it has become one of the research hotspots in the world in recent years. .

[0003] Cordycepin is an adenosine analog, because it can interfere with the synthesis of cellular DNA and RNA, inhibit the post-transcriptional modification of hnRNA and mRNA, inhibit the activation of adenylate cyclase, and can promote cell differentiation and rebuild the cytoskeleton, It enhances the chemotaxis of macrophages, inhibits the synthesis of specific proteins, and can also inhibit the activities of polyadenylate polymerase and protein kinase, thereby showing strong antibacterial, antiviral, and antitumor activities. It is a new type of broad-spectrum antibioti...

Examples

Embodiment 1

[0012] 1) Weigh 2.259g (0.009mol) of cordycepin and dissolve in 200mL of acetone (ultrasound-assisted dissolution).

[0013] 2) Under magnetic stirring and passing ammonia gas to saturation, then slowly drop 0.01 mol of alkanoyl chloride.

[0014] 3) The reaction system was incubated at 40° C. for 12 hours, and the reaction was terminated after the completion of the cordycepin reaction.

[0015] 4), after the solvent is recovered, the paste is dissolved in ethyl acetate and recrystallized to obtain the product. Yield 85%.

[0016] Synthetic process technology flow:

[0017]

[0018] Synthetic technology route

Embodiment 2

[0020] 1) Weigh 2.259g (0.009mol) of cordycepin and dissolve in 200mL of ether (ultrasound-assisted dissolution).

[0021] 2) Under magnetic stirring and passing ammonia gas to saturation, then slowly drop 0.01 mol of alkanoyl chloride.

[0022] 3) The reaction system was incubated at 80° C. for 1 hour, and the reaction was terminated after the completion of the reaction of cordycepin.

[0023] 4), after the solvent is recovered, the paste is dissolved in ethyl acetate, and the product can be obtained from crystallization. Yield 91%.

Embodiment 3

[0025] 1) Weigh 2.259g (0.009mol) of cordycepin and dissolve in 200mL of acetone (ultrasound-assisted dissolution).

[0026] 2) Under magnetic stirring and passing ammonia gas to saturation, then slowly drop 0.01 mol of alkanoyl chloride.

[0027] 3) The reaction system was incubated at 60° C. for 6 hours, and the reaction was terminated after the completion of the reaction of cordycepin.

[0028] 4), after the solvent is recovered, the paste is dissolved in ethyl acetate, and the product can be obtained from crystallization. Yield 88%.

[0029] supplementary form

[0030]

technical field

[0001] The invention relates to a new synthesis process of N-alkanoyl cordycepin. Background technique

[0002] Since Cunningham et al. isolated cordycepin (Cordycepin) from the culture liquid of Cordyceps militaris (L.) Link in 1951, its various biological activities have gradually been recognized by people, and it has become one of the research hotspots in the world in recent years. .

[0003] Cordycepin is an adenosine analog, because it can interfere with the synthesis of cellular DNA and RNA, inhibit the post-transcriptional modification of hnRNA and mRNA, inhibit the activation of adenylate cyclase, and can promote cell differentiation and rebuild the cytoskeleton, It enhances the chemotaxis of macrophages, inhibits the synthesis of specific proteins, and can also inhibit the activities of polyadenylate polymerase and protein kinase, thereby showing strong antibacterial, antiviral, and antitumor activities. It is a new type of broad-spectrum antibioti...

Examples

Embodiment 1

[0012] 1) Weigh 2.259g (0.009mol) of cordycepin and dissolve in 200mL of acetone (ultrasound-assisted dissolution).

[0013] 2) Under magnetic stirring and passing ammonia gas to saturation, then slowly drop 0.01 mol of alkanoyl chloride.

[0014] 3) The reaction system was incubated at 40° C. for 12 hours, and the reaction was terminated after the completion of the cordycepin reaction.

[0015] 4), after the solvent is recovered, the paste is dissolved in ethyl acetate and recrystallized to obtain the product. Yield 85%.

[0016] Synthetic process technology flow:

[0017]

[0018] Synthetic technology route

Embodiment 2

[0020] 1) Weigh 2.259g (0.009mol) of cordycepin and dissolve in 200mL of ether (ultrasound-assisted dissolution).

[0021] 2) Under magnetic stirring and passing ammonia gas to saturation, then slowly drop 0.01 mol of alkanoyl chloride.

[0022] 3) The reaction system was incubated at 80° C. for 1 hour, and the reaction was terminated after the completion of the reaction of cordycepin.

[0023] 4), after the solvent is recovered, the paste is dissolved in ethyl acetate, and the product can be obtained from crystallization. Yield 91%.

Embodiment 3

[0025] 1) Weigh 2.259g (0.009mol) of cordycepin and dissolve in 200mL of acetone (ultrasound-assisted dissolution).

[0026] 2) Under magnetic stirring and passing ammonia gas to saturation, then slowly drop 0.01 mol of alkanoyl chloride.

[0027] 3) The reaction system was incubated at 60° C. for 6 hours, and the reaction was terminated after the completion of the reaction of cordycepin.

[0028] 4), after the solvent is recovered, the paste is dissolved in ethyl acetate, and the product can be obtained from crystallization. Yield 88%.

[0029] supplementary form

[0030]

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