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Isoalantolactone derivative and salt thereof

A kind of technology of xerosalactone and its derivatives, which is applied in the direction of drug combination, carboxylate preparation, endocrine system diseases, etc., can solve the problems of poor water solubility, low bioavailability, short half-life, etc., and achieve improved survival, high The effect of tumor inhibition rate and excellent performance

Inactive Publication Date: 2017-03-08
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this document only discloses the data of in vitro tumor inhibition experiments on tumor cells. In animal experiments, we found that the oral toxicity of this compound is relatively high, it is difficult to be used in clinical practice, and its water solubility is not ideal. The effects of tumor inhibition experiments in animals and in vivo are not satisfactory, and have no clinical application value
Therefore, on the basis of the existing technology, the structure of inulin is modified, and a new derivative of inulin is provided to significantly improve its effect when used for the treatment of diseases such as cancer, and reduce its cytotoxicity, And by preparing the derivative into a derivative salt as a prodrug, it overcomes the shortcomings of the original drug such as poor water solubility, short half-life, and low bioavailability, which has become a problem to be solved urgently in the prior art

Method used

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  • Isoalantolactone derivative and salt thereof
  • Isoalantolactone derivative and salt thereof
  • Isoalantolactone derivative and salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of compound (II)

[0029]

[0030] 1) Preparation of compound (1.1)

[0031]

[0032] 1) Isoaurinolide (1.0g, 4.3mmol) was dissolved in dichloromethane (16mL), and peroxybenzoic acid (1.1g, 5.2mmol) was slowly added to the system in batches, reacted at room temperature for 3 hours, saturated The reaction was quenched with sodium thiosulfate (16 mL), extracted with dichloromethane (16 mL×3), the organic phase was washed with saturated aqueous sodium bicarbonate (16 mL), dried and concentrated, and purified by column chromatography (petroleum ether: ethyl acetate=20: 1) Obtain compound 1.2 (white solid, 984 mg, yield 92.0%).

[0033] 2) preparation of compound (I-II),

[0034]

[0035] The compound 1.2 obtained in step 1) was dissolved in dichloromethane (98mL), potassium carbonate (16.4g, 118.9mmol) and dimethylamine hydrochloride (4.8g, 59.4mmol) were added to the system in turn, and the mixed system was stirred Reflux reaction for 3 hours, after...

Embodiment 2

[0041] Preparation of compound (III)

[0042]

[0043] 1) Preparation of compound 1.3

[0044]

[0045] At 0°C, dissolve selenium dioxide (87.5mg, 0.75mmol) in dichloromethane (5mL), add tert-butanol peroxide (0.37mL), and stir for 30 minutes. , 2.15mmol) of dichloromethane (5mL) solution was slowly added to the above system, stirred at room temperature for 24 hours, quenched with saturated aqueous sodium thiosulfate (8mL), extracted with dichloromethane (8mL×3), dried Concentrate and purify by column chromatography (petroleum ether: ethyl acetate = 9:1 to 3:1) to obtain compound 1.23 (white solid, 350 mg, yield: 82.8%).

[0046] 2) Preparation of compound (I-III)

[0047]

[0048] The compound 1.3 obtained in the previous step was dissolved in dichloromethane (35mL), potassium carbonate (5.8g, 42.2mmol) and dimethylamine hydrochloride (1.7g, 21.1mmol) were added to the system successively, and the mixed system was stirred and refluxed Reacted for 3 hours. After th...

Embodiment 3

[0053] Preparation of Compound IV

[0054]

[0055] 1) Preparation of compound 1.4

[0056]

[0057] Compound 1.3 (112mg, 0.45mmol) was dissolved in dichloromethane (1mL), and a solution of peroxybenzoic acid (100mg, 0.60mmol) in dichloromethane (1mL) was slowly added dropwise to the above system, and reacted at room temperature for 2 hours , quenched the reaction with saturated sodium thiosulfate (2 mL), extracted with dichloromethane (2 mL×3), dried and concentrated, and purified by column chromatography (petroleum ether: ethyl acetate = 4:1 to 1:1) to obtain compound 1.4 ( White solid, 89 mg, yield: 74.5%).

[0058] 2) Preparation of compound (I-IV)

[0059]

[0060] The compound 1.4 obtained in the previous step was dissolved in dichloromethane (35mL), potassium carbonate (5.8g, 42.2mmol) and dimethylamine hydrochloride (1.7g, 21.1mmol) were added to the system successively, and the mixed system was stirred and refluxed Reacted for 3 hours. After the reaction, ...

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Abstract

The invention relates to isoalantolactone derivatives and salts thereof and provides an isoalantolactone derivative as shown in a formula (I). Salification acids are selected from inorganic acids or organic acids; the inorganic acids are selected from hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, boric acid, seleninic acid, phosphomolybdic acid, phosphorous acid and sulphurous acid; the organic acids are selected from citric acid, maleic acid, D-malic acid, L-malic acid, DL-malic acid, L-lactic acid, D-lactic acid, DL-acid, oxalic acid, methylsulfonic acid, pentanoic acid, oleic acid, lauric acid, p-toluene sulfonic acid, 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, phthalic acid, tartaric acid, malonic acid, succinic acid, fumaric acid, glycolic acid, mercaptan acid, glycine, sarcosine, sulfonic acid, nicotinic acid, methylpyridine acid, isonicotinic acid, benzoic acid or substituted benzoic acid.

Description

[0001] Technical field: [0002] The present invention relates to inulin derivatives and their salts and their application and preparation. [0003] Background technique: [0004] Inula helenium is a plant of the genus Inula in the family Compositae, a perennial herb whose roots are used for medicinal purposes. It has the functions of invigorating the spleen and harmonizing the stomach, regulating qi and relieving depression, relieving pain and preventing miscarriage. It is used for chest and flank, abdominal distension and pain, vomiting and diarrhea, chest and flank contusion, pain in the chest and flank, restless fetal movement and other diseases. Inulin volatile oil contains inulin, iso-inulin and other ingredients, its chemical structure is similar to Sandonian, it has anthelmintic effect on pigs, dogs, and cats, its curative effect is better than that of Sandonian, and its toxicity is lower. [0005] Isoauranthenolide (CAS: 470-17-7) belongs to sesquiterpenoids, and is o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/92C07D493/10C07C57/15C07C51/41A61K31/365A61P1/00A61P1/04A61P35/00A61P29/00A61P5/14A61P11/00A61P37/06
CPCC07D307/92C07D493/10
Inventor 杨诚杨光孙涛周红刚高险刘双伟盛彭真王常骅卢聘
Owner NANKAI UNIV
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