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Preparation method and application of euphorbia lathylris lathyrane type macrocyclic diterpene compounds

A caperane-type compound technology, which is applied in the field of preparation of caperane-type macrocyclic diterpene compounds, can solve problems such as toxicity

Active Publication Date: 2021-09-14
GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also has a certain toxicity

Method used

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  • Preparation method and application of euphorbia lathylris lathyrane type macrocyclic diterpene compounds
  • Preparation method and application of euphorbia lathylris lathyrane type macrocyclic diterpene compounds
  • Preparation method and application of euphorbia lathylris lathyrane type macrocyclic diterpene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the preparation of compound 1 to 5

[0049]

[0050] Soak the caper seed (8kg) with 95% ethanol (75L * 3), obtain 817.2g crude extract. The extract was dispersed in water (3L), and extracted with petroleum ether, ethyl acetate and n-butanol respectively. Carry out gradient elution (MeOH / H 2 O, 6:4→10:0) were separated and divided into three parts (Fr.I-III). The Fr.II fraction (215.6g) was separated into four fractions (Fr.IIA-IID) by normal phase silica gel column chromatography (PE / EtOAc, 50:1→1:1). Fragment Fr.IIC (2.9g) by reverse phase C 18 Silica gel column chromatography (MeOH / H 2 O,6:4→10:0) is separated into five parts (Fr.IIC 1 -IIC 5 ), where Fr.IIC 1 Part (132.2 mg) was passed through normal phase silica gel column chromatography (CH 2 Cl 2 / MeOH,100:1→0:1) gradient elution separation and semi-preparative chiral separation HPLC (MeCN / H 2 (0,75 / 25,3mL / min) was purified to obtain compound 3 (34mg, t R 13.0min). Fr.IIC 2 Fragment ...

Embodiment 2

[0062] Embodiment 2: the preparation of compound 8

[0063]

[0064] Fr.IIC in Example 1 2 Fragment (1.435g) was separated by Sephadex LH-20 gel column (MeOH) and normal phase silica gel column chromatography (PE / EtOAc, 10:1→0:1) to obtain three segments (Fr.IIC 2a -IIC 2c ). Fr.IIC 2a (207.2 mg) was separated by normal phase silica gel column chromatography (PE / EtOAc, 15:1→0:1) and then separated by semi-preparative chiral HPLC (MeCN / H 2 (0,70 / 30,3mL / min) to obtain compound 8 (67.3mg, t R 8.9min).

[0065] figure 1 with figure 2 They are the proton NMR spectrum, carbon spectrum and DEPT135 spectrum of compound 8, respectively. Its spectral data is consistent with that of the known compound Euphorbia Factor L 9 unanimous.

Embodiment 3

[0066] Embodiment 3: the preparation of compound 17

[0067]

[0068]Compound 15 (30 mg, 0.047 mmol) was dissolved in 2 mL of methanol, 1% sodium hydroxide was added, and reacted at room temperature for 1 hour. After quenching the reaction solution with 5 mL of water, it was extracted with ethyl acetate (5 mL×3). The organic layer was concentrated and spin-dried, and purified by silica gel column chromatography CC (PE / EtOAc, 10:1) to obtain compound 17 (15.3 mg).

[0069] Its spectral data are consistent with those reported in the literature, so its structure is confirmed.

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Abstract

The invention discloses a preparation method and application of euphorbia lathylris lathyrane type macrocyclic diterpene compounds. The euphorbia lathylris lathyrane type macrocyclic diterpene compounds are used for preparing anti-cholestasis drugs for the first time. Cell experiment results show that the euphorbia lathylris lathyrane type macrocyclic diterpene compounds have good pregnane X receptor agonistic activity and anti-cholestasis activity, and are expected to be developed into novel pregnane X receptor agonists and anti-cholestasis drugs.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method and application of a class of scaperoid-type macrocyclic diterpene compounds. Background technique [0002] Cholestasis is an important pathological process of progressive bile secretion and excretion disorders that eventually lead to a series of hepatobiliary diseases. Long-term cholestasis usually causes a series of hepatobiliary diseases, such as primary biliary cirrhosis, primary sclerosing cholangitis, etc., and eventually develops into liver fibrosis or even cirrhosis, which seriously threatens human life and health. According to statistics, about 60% of the above-mentioned patients with hepatobiliary diseases are accompanied by cholestasis. At present, there are only two anti-cholestasis drugs approved by the FDA, which can improve the symptoms of patients to a certain extent, but there are also serious adverse reactions such as abnormal thyroid function and a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/122A61K31/336A61K31/341A61K31/381A61K31/4406A61K31/235A61K31/216A61K31/22A61K31/4427A61P1/16C07C67/48C07C67/56C07C69/78C07C69/618C07C69/21C07D213/80C07D213/803C07D405/12C07D303/32C07D301/32C07C45/64C07C49/743C07D307/68C07D333/38C07D493/10C07C67/29C07C67/283C07C67/293
CPCA61K31/122A61K31/336A61K31/341A61K31/381A61K31/4406A61K31/235A61K31/216A61K31/22A61K31/4427A61P1/16C07C67/48C07C67/56C07C69/78C07C69/618C07C69/21C07D213/80C07D213/803C07D405/12C07D303/32C07D301/32C07C45/64C07C49/743C07D307/68C07D333/38C07D493/10C07C67/29C07C67/283C07C67/293C07B2200/07C07C2603/38
Inventor 毕惠嫦尹胜刘培庆黄冬
Owner GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK
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