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Preparation method and application of D-dencichine

A technology of notoginseng and trifluoroacetoxy, which is applied in the fields of medicinal chemistry and therapeutics, can solve problems such as ineffective effects, and achieve good effects in treating thrombocytopenia, simple preparation process, and high yield.

Pending Publication Date: 2016-03-30
INST OF MEDICINAL PLANT DEV CHINESE ACADEMY OF MEDICAL SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, these drugs may not have obvious effects or have various unsatisfactory side effects in clinical use. For example, interleukin-11 has side effects such as edema, pain at the injection site, redness, induration, and conjunctival congestion.

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  • Preparation method and application of D-dencichine
  • Preparation method and application of D-dencichine
  • Preparation method and application of D-dencichine

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preparation example Construction

[0032] The preparation method of D-notoginseng provided by the invention comprises the following steps:

[0033] 1) performing Fmoc protection on the amino group of D-asparagine to obtain the first intermediate S-D-1;

[0034] 2) performing a Hoffman degradation reaction on the first intermediate S-D-1 to obtain a second intermediate S-D-2;

[0035] 3) under the action of an organic base, remove the Fmoc protection of the second intermediate S-D-2 to obtain the third intermediate S-D-3;

[0036] 4) Condensation reaction of the third intermediate S-D-2 with monopotassium oxalate under strong alkali conditions to obtain the target product D-notoginseng.

[0037] The synthetic route of D-notoginseng is as follows:

[0038]

Embodiment 1D- 10

[0039] The synthetic method of embodiment 1D-notoginseng

[0040] 1) Synthesis of the first intermediate S-D-1:

[0041] Take D-asparagine monohydrate (8.7g, 58mmol) in a round bottom flask, add distilled water 300mL, then add sodium bicarbonate (10.9g, 130mmol) and stir well; take 9-fluorenylmethyl-N-succinyl Imidocarbonate (20g, 60mmol) was dissolved in 150mL of acetone, and the acetone solution of the 9-fluorenylmethyl-N-succinimidylcarbonate was slowly added dropwise to the above-mentioned round-bottomed flask. The reaction was stirred for 4 hours; the pH value of the product solution was adjusted to 3 with concentrated hydrochloric acid, and then the product solution was filtered with suction to obtain 19.5 g of white solid, namely the first intermediate S-D-1, with a yield of 95%.

[0042] 2) Synthesis of the second intermediate S-D-2:

[0043] Take (24.9g, 56mmol) [bis(trifluoroacetoxy)iodo]benzene (PIFA) in a round bottom flask, add 58mL of acetonitrile to dissolve; ...

Embodiment 2

[0053] 1) Synthesis of the first intermediate S-D-1:

[0054] Take D-asparagine monohydrate (9.0g, 60mmol) in a round bottom flask, add distilled water 310mL, then add sodium bicarbonate (10.911.2g, 134mmol) and stir well; take 9-fluorenylmethyl-N-succinate Imidocarbonate (21g, 62mmol) was dissolved in 155mL of acetone, and the acetone solution of 9-fluorenylmethyl-N-succinimidylcarbonate was slowly added dropwise to the above-mentioned round-bottomed flask. The reaction was stirred for 3.5 hours; the pH value of the product solution was adjusted to 2.5 with concentrated hydrochloric acid, and then the product solution was filtered with suction to obtain 19.8 g of white solid, namely the first intermediate S-D-1, with a yield of 93%.

[0055] 2) Synthesis of the second intermediate S-D-2:

[0056] Take (24.9g, 56mmol) [bis(trifluoroacetoxy)iodo]benzene (PIFA) in a round bottom flask, add 58mL of acetonitrile to dissolve; take another (19.2g, 54.2mmol) S-D-1, dissolve in 115mL...

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Abstract

The invention discloses a preparation method and application of D-dencichine. The preparation method comprises the following steps: carrying out Fmoc protection on the amino group of D-asparagine so as to obtain a first intermediate; subjecting the first intermediate to Hoffman degradation reaction so as to obtain a second intermediate; subjecting the second intermediate to removal of Fmoc protection under the action of organic base so as to obtain a third intermediate; and subjecting the third intermediate and monomethyl oxalate to condensation reaction under a highly basic condition so as to obtain D-dencichine. D-dencichine is prepared by using the high-efficiency safe preparation method; the preparation method is simple and has high yield; the compound D-dencichine prepared by using the method has good treatment effect on thrombocytopenia and the effect is better than the effect of a clinical medicine interleukin-11, so D-dencichine can be used as a candidate medicine for treating thrombocytopenia.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and therapeutics, in particular to a preparation method of D-notoginseng (ie β-N-oxalyl-D-α, β-diaminopropionic acid) and its application. Background technique [0002] Thrombocytopenia refers to a condition caused by the number of platelets below the normal range. Thrombocytopenia may result from insufficient production of platelets, retention of platelets by the spleen, increased destruction or utilization of platelets, and dilution, regardless of the cause. Thrombocytopenia, all of which can cause typical bleeding: multiple ecchymosis, most often on the lower legs; or small scattered ecchymosis at the site of minor trauma; mucosal bleeding, epistaxis, gastrointestinal and genitourinary and vaginal Bleeding, and massive bleeding after surgery, massive gastrointestinal bleeding, and bleeding within the central nervous system can be life-threatening. [0003] At present, the commonly used clin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/56C07B57/00A61K31/197A61P7/00
CPCC07C269/04C07B57/00C07B2200/07C07C227/20C07C231/02C07C269/06
Inventor 孙晓波许旭东田瑜孙桂波王敏
Owner INST OF MEDICINAL PLANT DEV CHINESE ACADEMY OF MEDICAL SCI
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