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Aporphine type alkaloid and preparation method thereof

A technology of alkaloids and apophyll, applied in the field of organic synthetic chemistry, can solve the problems of dehydrogenation, no anti-cancer activity, poor stability, etc.

Inactive Publication Date: 2016-02-10
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the study of anticancer activity in animals, it was found that the stability of the compound in aqueous solution was poor, and its anticancer effect in vivo was inconsistent with that in vitro. The main reason was that the drug was absorbed and distributed in the body and before it took effect. It must go through the metabolic first-pass effect of the liver. 8-Amino-isocreidine passes through the first-pass effect, undergoes oxidation-reduction or metabolic transformation of liver drug enzymes, and its prototype drug is inactivated, so it does not show anti-cancer activity in vivo
At the same time, in the study on the stability of 8-amino-isoxridine, it was found that it is not stable in aqueous solution, and it is easy to undergo oxidation reaction conversion of dehydrogenation. The main reason is that the chemical structure of the compound has a p-aminophenol structure. Fragment, unstable in aqueous solution, prone to chemical transformation

Method used

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  • Aporphine type alkaloid and preparation method thereof
  • Aporphine type alkaloid and preparation method thereof
  • Aporphine type alkaloid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of 8-acetamido-isocredine:

[0025] Dissolve 6g of the reaction raw material 8-amino-isocredine in 20mL of ethyl acetate, stir mechanically to dissolve the reaction raw material completely, add 60mL redistilled acylating reagent acetyl chloride dropwise under mechanical stirring, react for 2h, and identify the reaction by TLC Completely, adjust the pH value of the above reaction product to about 7 with ammonia water, pour the reaction solution into 200mL ice water, extract three times with 300mL chloroform, combine the organic phases, recover the organic solvent, and separate the extract by silica gel column chromatography to obtain 8-acetylamino- Isocridine 5.3g;

[0026]

Embodiment 2

[0027] Embodiment 2: the preparation of 8-acetamido-isocredine:

[0028]The reaction raw material 8-amino-isocredine 6g was dissolved in 20mL chloroform, mechanically stirred, and added dropwise to 60mL redistilled acylating reagent acetyl chloride, reacted for 2h, and the reaction was identified by thin-layer chromatography. Adjust the pH value to about 7, pour the reaction solution into 200mL ice water, extract three times with 300mL chloroform, combine the organic phases, recover the solvent to dryness under reduced pressure, dissolve in 10mL methanol, mix the sample on a silica gel column, and perform column chromatography separation to obtain 8- Acetylamino - isocridine hydrochloride 5.1g;

Embodiment 3

[0029] Embodiment 3: the synthesis of 8-acetamido-isocredine:

[0030] Dissolve 6 g of the reaction material 8-amino-isocreidine in 30 mL of ethyl acetate, mechanically stir to dissolve all the reactants, add 60 mL of freshly distilled acetic anhydride dropwise, react for 2 hours, and adjust the pH value of the above reaction product to 7 or so, pour the reaction liquid into 200mL of ice water, extract three times with 300mL of dichloromethane, combine the organic phase, recover the organic solvent, and separate the extract by silica gel column chromatography to obtain 4.9g of 8-acetylamino-isoxridine;

[0031]

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PUM

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Abstract

The invention discloses an aporphine type alkaloid and a preparation method thereof. The compound is 8-acetamido-isocorydine, which is prepared through the nucleophilic substitution reactions between 8-amino-isocorydine, and the chemical structure formula of the compound is represented in the description. Through a Kunming white mouse tumor xenograft model, the results show that the provided alkaloid has a strong effect on inhibiting the tumor growth in body and has a good antitumor activity.

Description

technical field [0001] The present invention relates to pharmaceutical synthetic chemistry, and belongs to the field of organic synthetic chemistry. Specifically, the present invention relates to a kind of aporphylloid alkaloid and its preparation method. Background technique [0002] Isochorydine is a typical aporphenite alkaloid, and the research on the chemical composition of natural products has shown that the main apophenite-like isoquinoline alkaloids are contained in baldhead flower (Chang Xingruo, Wang Hongxin, Zhou Guangzhi. baldhead flower chemistry Research on composition and histomorphology. Journal of Drug Analysis, 1982, 2, 273-277; Liu Dahu et al., Research on chemical constituents of alkaloids in bald sore flower, Chinese herbal medicine, 2011, 8(42): 1505-1508; YanDang, etal ., Alkaloid from Dicranostigmaleptopodum (Maxim) Fedde, Chin Chem Lett, 2009, 20, 1218-1220.; Mei Zhong, etal ., Anewquaternaryprotoberberinealkaloidisolatedfrom Dicranostigmaleptop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18A61P35/00
Inventor 柳军玺邸多隆钟梅
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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