Synthesis of 1-substituent-5-isopropyl-3, 8-dimethyl azulenyl sulfonyl piperazine and anti-gastric ulcer activity research

A kind of technology of dimethylazulene sulfonylpiperazine and substituent, which is applied in the field of guaiazulene derivatives, and can solve problems such as increasing number of people

Active Publication Date: 2013-06-19
SICHUAN GUOKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are many drugs to treat stomach ulcers caused by different fa

Method used

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  • Synthesis of 1-substituent-5-isopropyl-3, 8-dimethyl azulenyl sulfonyl piperazine and anti-gastric ulcer activity research
  • Synthesis of 1-substituent-5-isopropyl-3, 8-dimethyl azulenyl sulfonyl piperazine and anti-gastric ulcer activity research
  • Synthesis of 1-substituent-5-isopropyl-3, 8-dimethyl azulenyl sulfonyl piperazine and anti-gastric ulcer activity research

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1: This example prepares 5-isopropyl-3,8-dimethylazulenesulfonylpiperazine (abbreviated as A)

[0071]

[0072] The processing steps of the present embodiment are as follows:

[0073] Weigh azulene sulfonate sodium (1mmol) in a 25mL round bottom flask, add 10mL CH 2 Cl 2 , and add 3-5 drops of DMF and 0.5 mL of pyridine; add a small amount of CH to the dropping funnel 2 Cl 2 and add (COCl) 2 (2.5mmol), and then slowly added dropwise to the round bottom flask. After the reaction, slowly add 2 mL of Et 3 N, 1 mL of a mixture of pyridine and 3-bromoaniline (1.5 mmol). After the dropwise addition, react at room temperature for 1 hour, then add water corresponding to its volume to the reaction flask, adjust the pH to 5-6 with dilute hydrochloric acid, and 2 Cl 2 Extraction, the organic layer was washed with anhydrous Na 2 SO 4 Dry and spin dry, and the crude product is purified by column chromatography to obtain 5-isopropyl-3,8-dimethylazulenesulfonylpip...

Embodiment 2

[0074] Example 2: This example prepares 1-(benzenesulfonyl)-3,8-dimethyl-5-isopropyl-1-azulenesulfonylpiperazine (abbreviated as A1)

[0075]

[0076] The processing steps of the present embodiment are as follows:

[0077] Add 10ml of anhydrous THF to a 25mL pear-shaped bottle, then add 0.5g of NaH, and then add 0.2g of 1-substituent-5-isopropyl-3,8-dimethylazulenesulfonylpiperazine in which R is H , then add benzenesulfonyl chloride respectively, make it react at room temperature, the time varies, then add water equivalent to its volume in the reaction flask, extract with ethyl acetate and spin dry, and the crude product is purified by column chromatography to obtain 1-( Benzenesulfonyl)-3,8-dimethyl-5-isopropyl-1-azulenesulfonylpiperazine (purple crystal), yield 56.9%, m.p.158-160℃.IR(KBr): 3443, 2961 , 2930, 2842, 1543, 1445, 1355, 1327, 1305, 1264, 1174, 1149, 1095, 944, 898; 1 H NMR (400MHz, CDCl 3 )δ(ppm): 8.27(s, 1H), 8.01(s, 1H), 7.74(d, J=7.2Hz, 1H), 7.50~7.65(m...

Embodiment 3

[0078] Example 3: This example prepares 1-(p-toluenesulfonyl)-5-isopropyl-3,8-dimethyl-1-azulenesulfonylpiperazine (abbreviated as A2)

[0079]

[0080] The processing steps of the present embodiment are as follows:

[0081] Add 10ml of anhydrous THF to a 25mL pear-shaped bottle, then add 0.5g of NaH, and then add 0.2g of 1-substituent-5-isopropyl-3,8-dimethylazulenesulfonylpiperazine in which R is H , and then add p-toluenesulfonyl chloride respectively, make it react at room temperature, the time varies, then add water corresponding to its volume in the reaction flask, extract with ethyl acetate and spin dry, and the crude product is purified by column chromatography to obtain 1- (p-toluenesulfonyl)-5-isopropyl-3,8-dimethyl-1-azulenesulfonylpiperazine (purple crystal), yield 48.4%, m.p.123-125℃.IR(KBr): 3458 , 2962, 2360, 1635, 1455, 1332, 1311, 1270, 1147, 1096, 949, 727, 704; 1 H NMR (400MHz, CDCl 3 )δ(ppm): 8.27(s, 1H), 8.00(s, 1H), 7.57~7.63(m, 3H), 7.26~7.37(m, 3H...

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Abstract

The invention discloses a guaiazulene derivative 1-substituent-5-isopropyl-3, 8-dimethyl azulene sulfonyl piperazine, wherein the structural formula is as follows: in which R is C6H5O2S, 4-CH3C6H4, COCH3, SO2CH3, COCH2C1, COC6H5, 1-SO2-4-BrC6H4, CH2C6H5, CH2CO2C2H5, CH3, COCF3, iso-C3H7, C4H9, 1-CH2-4-CH3C6H4, 1-CH2-2-C1C6H4, n-C3H7, C2H5, and other substances are respectively represented by A, A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16 and A17. Part of compounds can remarkably alleviate the pathological degree of gastric ulcer of mice by absolute ethyl alcohol, and the gastric ulcer fraction is remarkably different from that of a model. The preparation method comprises preparation of 1-substituent-5-isopropyl-3, 8-dimethyl azulene sulfonyl piperazine.

Description

technical field [0001] The invention relates to guaiazulene derivatives, preparation methods of guaiazulene derivatives and uses of guaiazulene derivatives. Background technique [0002] Guaiazulene, that is, 1,4-dimethyl-7-isopropylazulene (1,4-dimethyl-7-isoproylazulene, Guiaazulene), is an active ingredient of the plant chamomile, and its structural formula is as follows: [0003] [0004] Guaiazulene has strong anti-pepsin, anti-inflammatory, anti-allergic, and promoting mucosal metabolism functions, and many of its derivatives have shown good biological activities. Compound guaiazulene ointment (Shanxi Tongsheng Pharmaceutical Co., Ltd.) can be used for burns, scalds, burns, frostbite, chapped, decubitus, radiation heat protection, dermatitis, etc. Sodium azulene sulfonate is a water-soluble derivative of guaiazulene, which has good anti-inflammatory and wound-healing properties, and is also the main component of glutamine granules, a drug currently on the market fo...

Claims

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Application Information

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IPC IPC(8): C07D295/26A61P1/04
Inventor 袁明兴石万棋徐琨张露昀董林李颖尹述凡
Owner SICHUAN GUOKANG PHARMA
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