Preparation and use of compounds i.e., 1,3-dihydroxy-5-alkyl benzene as inhbitor of protein-tyrosine-phosphatase 1B

A compound, the technology of alkylbenzene, applied in the field of medicine, can solve problems such as unseen

Inactive Publication Date: 2009-07-01
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The present invention is the first time to obtain 1,3-dihydroxy-5-alkylbenzene compounds from the mangrove plant Prunus alba, and obtain their methylated and acetylated compounds through derivatization reaction. It has been shown that this type of compound has significant activity of inhibiting protein tyrosine phosphatase 1B, but there is no report of this type of compound having this activity through literature search

Method used

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  • Preparation and use of compounds i.e., 1,3-dihydroxy-5-alkyl benzene as inhbitor of protein-tyrosine-phosphatase 1B
  • Preparation and use of compounds i.e., 1,3-dihydroxy-5-alkyl benzene as inhbitor of protein-tyrosine-phosphatase 1B
  • Preparation and use of compounds i.e., 1,3-dihydroxy-5-alkyl benzene as inhbitor of protein-tyrosine-phosphatase 1B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of compound 2-methyl-5-tridecyl-1,3-benzenediol (2-methyl-5-tridecyl-1,3-benzodiol)

[0032] Olive plum 3.0kg was leached three times with methanol, each time for one week, the methanol extract was combined, methanol was removed under reduced pressure, and then H 2 O was dissolved, then extracted three times with petroleum ether, ethyl acetate, and n-butanol respectively, and the ethyl acetate was combined and evaporated to dryness to obtain 28 g of extract.

[0033] Put 28g of ethyl acetate extract on a silica gel (100-200 mesh) column, elute with petroleum ether / ethyl acetate 95:5-50:50, 500ml / part, 100 parts in total, and combine after detection by thin layer chromatography There are 15 parts, and the fourth part is subjected to silica gel (200-300 mesh) column chromatography, eluted with petroleum ether / diethyl ether 90:10-50:50, and divided into F41 (500mg), F42 (850mg), F43 (350mg) three parts, F41 is subjected to Sephadex LH-20 gel column ...

Embodiment 2

[0035] Example 2: Preparation of compound 1,3-dihydroxy-5-undecylbenzene (1,3-dihydroxy-5-undecylbenzene)

[0036] Put 28g of ethyl acetate extract on a silica gel (100-200 mesh) column, elute with petroleum ether / ethyl acetate 95:5-50:50, 500ml / part, 100 parts in total, and combine after detection by thin layer chromatography There were 15 fractions, and the fifth fraction was subjected to silica gel (200-300 mesh) column chromatography, eluted with petroleum ether / ethyl acetate 90:10-50:50, 100ml / part, 90 parts in total. Thin-layer chromatography detection, developer petroleum ether / diethyl ether (1:1), combined into three parts, F51 (29-36, 2.0g), F52 (40-55, 500mg), F53 (65-85, 200mg ); F52 is subjected to Sephadex LH-20 gel column chromatography again, with CHCl 3 / MeOH (1:1) elution, 5ml / part, 30 parts in total, TLC detection, developer petroleum ether / diethyl ether (1:1), combined into F521 (10-19, 300mg) and F522 (25 -29, 90mg) two parts; F522 is through Sephadex LH-...

Embodiment 3

[0038] Example 3: Preparation of Compound 1 and Compound 2 Derivatives

[0039] (1) Preparation of compound 1 and compound 2 methylate

[0040] Weigh 5.0mg of compound 1 and compound 2 samples into a 10mL round-bottomed flask, add dissolved CH 2 N 2 Diethyl ether solution 2mL, evaporate ether and CH 2 N 2 Afterwards, the methylate of compound 1 (n=10, R 3 =CH 3 , R 1 , R 2 =CH 3 ) and the methylate of compound 2 (n=8, R 3 = H, R 1 , R 2 =CH 3 )

[0041] (2) Preparation of compound 1 and compound 2 acetylate

[0042] Weigh 5.0 mg of compound 1 and compound 2 samples into a 25 mL round bottom flask, add 1.5 mL of anhydrous pyridine and acetic anhydride, stir on a magnetic stirrer for 24 h, remove pyridine and acetic anhydride under reduced pressure, and obtain the acetyl compound (n=10, R 3 =CH 3 , R 1 , R 2 =Ac) and the acetylated compound of compound 2 (n=8, R 3 = H, R 1 , R 2 =Ac).

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PUM

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Abstract

Production of 1,3-dihydroxy-5-alkylamine compound with protein tyrosine phosphatase 1B inhibiting activity extracted and separated from branches and leaves of Lumnitzera racemosa Willd and its use are disclosed. R1 and R2 is H or Ac, R3 is H or CH3, n=8 or 10. It is carried out by drying and breaking branches and leaves of Lumnitzera racemosa, extracting by methyl alcohol, extracting the subsection of light petroleum, acetic ether and (n-)butanol, silica gel column and Sephadex LH-20 gel column chromatographing the part of acetic ether, separating to obtain monomer compound, analyzing by wave spectrum, determining 1,3-dihydroxy-5-alkylamine compound, acetylating and methylating reacting, and obtaining acetylate and methylate. It has PTP1B inhibiting activity and can be used for diabetes mellitus and obesity.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a 1,3-dihydroxy-5-alkyl group isolated and derivatized from the mangrove plant Prunus spp. Preparation method and application of benzene compounds. The compounds can be used as protein tyrosine phosphatase 1B inhibitors and insulin sensitizers, and can be used to treat various diabetes, obesity and other complications caused by them. technical background [0002] Diabetes mellitus (diabetes mellitus) is a group of clinical syndromes caused by the interaction of genetic and environmental factors. Due to the absolute or relative insufficiency of insulin secretion and the decreased sensitivity of target tissue cells to insulin, sugar, protein, fat, water and electrolytes, etc. A range of metabolic disorders. Clinically, hyperglycemia is the main common sign. Prolonged illness can cause damage to multiple systems. Acute metabolic disorders such as ketoacidosis can occur when the c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/70C07C39/08A61K31/05A61P3/04A61P3/10A61P5/50
Inventor 郭跃伟王继栋李佳南发俊于嘉陵周秀红
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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