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Compound with novel structure and preparation method and applications thereof

A compound, hydrogen sulfide technology, applied in the field of medicine, to achieve the effect of reducing cardiovascular events, high pharmacological activity, and broad application prospects

Inactive Publication Date: 2012-06-20
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In order to solve the problems existing in the prior art, the present inventor introduced a hydrogen sulfide releasing group into the structure of oleanolic acid through a large number of experiments, and synthesized a series of new compounds, which effectively overcome the defects of the prior art

Method used

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  • Compound with novel structure and preparation method and applications thereof
  • Compound with novel structure and preparation method and applications thereof
  • Compound with novel structure and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 1. Synthesis of 5-(4-hydroxyphenyl)-3H-1,2-dithiocyclopentyl-4-ene-3-thione (ADT-OH)

[0045] (1) 5-(4-methoxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OCH 3 )Synthesis

[0046] Add anethole (3.17g, 0.021mol), sulfur (4.70g, 0.146mol) and DMF30mL into the flask, stir and reflux for 6h. Pour into cold water after the reaction, a large amount of precipitates precipitated out, filtered, and recrystallized from ethanol-water to obtain red crystals with a yield of 78%, mp: 110~111°C.

[0047] 1 H NMR (400MHz, DMSO-d 6 ), δ(ppm): 7.62 (d, 2H, J = 8.9 Hz, ArH), 7.40 (s, 1H, =CH), 6.98 (d, 2H, J = 8.8 Hz, ArH), 3.88 (s, 3H, OCH 3 ).

[0048] (2) Synthesis of 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OH)

[0049] ADT-OCH 3 (20.6g, 0.1mol) and pyridine hydrochloride (69.0g, 0.6mol) were heated to reflux for 1h, cooled, turned into a solid, smashed, washed several times with water, filtered, and the filter cake was recrystallized with acetone-water, the yield was...

Embodiment 2

[0100] Synthesis of YLXY Ⅲ and Ⅳ Compounds

[0101] (1) Synthesis of oleanolic acid 2-[4-(3H-1, 2-dithiol-3-thione-5-yl)-phenoxy]ethyl ester (YLXYⅢ-1)

[0102] Will ADT-OH (0.147g, 0.65mmol), oleanolic acid-2-bromoethyl ester ( 9a ) (0.365 g, 0.65mmol), anhydrous K 2 CO 3 (0.178g, 1.30mmol) and a catalytic amount of KI were added to 10mL dry DMF, stirred at room temperature for 12h, then diluted with 10mL ethyl acetate, washed with water (3×10mL), anhydrous Na 2 SO 4 Dry, evaporate the solvent to dryness, and perform column chromatography [petroleum ether (60-90):ethyl acetate=20:1 (v / v)] to obtain 0.259 g of a red solid with a yield of 56.2%, mp: 101.0~102.0°C.

[0103] 1 H NMR (400 MHz, CDCl 3 ) , δ: 7.62 (d, 2H, J = 8.8 Hz, ArH), 7.39 (s, 1H, =CH), 6.97 (d, 2H, J = 8.8 Hz, ArH), 5.24 (brs, 1H, C 12 -H), 4.41 (m, 2H, OCH 2 ), 4.21 (t, 2H, OCH 2 ), 3.19 (dd, 1H, 3α-H), 2.86 (d, 1H, C 18 -H), 1.11 (s, 3H, CH 3 ), 0.97 (s, 3H, CH 3 ), 0.91 (s, 3H, CH 3 ), ...

Embodiment 3

[0140] (1) 3-[4-(3H-1, 2-dithiol-3-thione-5-yl)-phenoxy]propyl 3-oxooleanolic acid (YLXYⅣ-1 )Synthesis

[0141] Referring to the synthetic method of YLXYⅢ-1, 3-oxooleanolic acid and 3b Preparation, red powder, yield 82.6%, mp: 91.6~92.5℃.

[0142] 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 7.62 (d, 2H, J = 8.7 Hz, ArH), 7.40 (s, 1H, =CH), 6.96 (d, 2H, J = 8.7 Hz, ArH), 5.26 (s, 1H, C 12 -H), 4.30-4.16 (m, 2H, OCH 2 ), 4.15-4.05 (m, 2H, OCH 2 ), 2.88 (m, 1H, C 18 -H), 2.57-2.47 (m, 1H, C 2 -H), 2.39-2.28 (m, 1H, C 2 -H), 2.15 (p, 2H, CH 2 ), 1.10 (s, 3H, CH 3 ), 1.05 (s, 3H, CH 3 ), 1.00 (s, 3H, CH 3 ), 0.93 (s, 3H, CH 3 ), 0.91 (s, 3H, CH 3 ), 0.89 (s, 3H, CH 3 ), 0.66 (s, 3H, CH 3 ).

[0143] IR(KBr, cm -1 ): 1716.7 (C=O), 1701.0 (C=O), 1662.4, 1601.0, 1576.8, 1490.3 (C=C), 1177.5 (C=S).

[0144] HR-MS: Calcd. For C 42 h 57 o 4 S 3 [M+H]+ 721.3413, Found: 721.3413.

[0145] (2) 4-[4-(3H-1,2-dithiol-3-thione-5-yl)-phenoxy]butyl 3-oxooleanolic acid (YLXYⅣ...

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Abstract

The invention discloses a compound with a novel structure and a preparation method and applications thereof. The compound comprises a part related to hydrogen sulfide and is generally covalently bonded with compounds or forms a salt. The structural formula is shown. The results of pharmacological experiments show that the compound has significant anti-inflammatory and anti-tumor effects without obvious gastrointestinal tract damage. The compound can be used for preparing medicines for treating various diseases, in particular diseases related to inflammation, heart and blood vessels and tumor. In addition, the invention also provides a method for preparing the compound.

Description

technical field [0001] The present invention relates to the field of medicine, in particular to a class of chianolic acid derivatives and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions containing these derivatives and their medical uses, especially in the preparation of anti-inflammatory , anti-tumor and anti-cardiovascular disease drugs. Background technique: [0002] Oleanolic acid (OA) is a pentacyclic triterpenoid compound, a chemical component of natural products, widely distributed in the plant kingdom, according to incomplete statistics, 126 kinds of plants contain OA. Among the commonly used plants, such as clove, jujube, western Sichuan watercress, privet privet, achyranthes bidentata, American ginseng, storax, forsythia, green leaf gallbladder, pipa leaf, persimmon leaf, sedum notoginseng, ginseng, mountain sesame , Licorice, Guan Mutong, Northeast Gentian, Xuedan, Yamu, Cumin, Prunella all contain OA. OA main...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/58A61K31/56A61P29/00A61P9/00A61P25/00A61P11/00A61P1/00A61P7/00A61P35/00A61P3/00
Inventor 邱婷史方超成静绪广林盛晶晶郑文杰敖桂珍
Owner NANJING NORMAL UNIVERSITY
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