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Protein antagonist with water channel

An aquaporin and antagonist technology, which is applied in the field of aquaporin antagonists to achieve the effects of high accuracy, less interference and good reproducibility

Inactive Publication Date: 2006-03-15
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no report that the compound with the parent structure of 1,3,4-thiadiazole has the effect of aquaporin antagonist

Method used

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  • Protein antagonist with water channel
  • Protein antagonist with water channel
  • Protein antagonist with water channel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 N 1 -(5-n-Butyl-1,3,4-thiadiazol-2-yl)-N3-m-chlorophenylurea

[0023] A. Synthesis of intermediate 5-n-butyl-2-amino-1,3,4-thiadiazole

[0024] Put 0.05mol of n-valeric acid and 0.07mol of thiosemicarbazide into a 100mL three-necked flask respectively, add 11mL of concentrated sulfuric acid dropwise under stirring at room temperature, then heat for 8h, keep the temperature at 80-90°C, cool to room temperature, and react Slowly pour the solution into ice water, neutralize it with 40% sodium hydroxide solution to pH=8-9, let it sit overnight, filter it with suction, wash the solid crude product with water for 2-3 times, and recrystallize it with water or dilute ethanol solution to obtain Pure product, yield 70%, m.p.219-220°C.

[0025] B.N. 1 -(5-n-butyl-1,3,4-thiadiazol-2-yl)-N 3 -Synthesis of m-chlorophenylurea

[0026] Dissolve 2mmol of 5-n-butyl-2-amino-1,3,4-thiadiazole in 10mL of anhydrous acetonitrile, slowly add 2mmol of m-chlorophenyl isocyanate in...

Embodiment 25

[0030] Example 25 N 1 -(5-n-butyl-1,3,4-thiadiazol-2-yl)-N 3 -3,4-Dichlorophenylthiourea

[0031] Dissolve 2mmol of 5-n-butyl-2-amino-1,3,4-thiadiazole in 10mL of anhydrous acetonitrile, slowly add 2mmol of 3,4-dichlorophenylisothiocyanate dropwise at room temperature After adding 2 mL of anhydrous acetonitrile solution, reflux until the reaction was complete (TLC followed the reaction progress). After cooling, a large amount of white solids were precipitated, and the precipitated solids were filtered, followed by column chromatography with ethyl acetate / petroleum ether to obtain a pure product with a yield of 70%, m.p.>260°C.

[0032] 1 H-NMR (300MHz, DMSO-d 6 ): δ0.89(t, 3H, CH 3 ), 1.34(m, 2H, CH2), 1.65(m, 2H, CH2), 2.84(t, 2H, CH2), 7.42~7.69(m, 3H, C6H3), 10.05(s, 1H, NH), 13.78 (bs, 1H, NH).

[0033] Example

Embodiment 40

[0034] Example 40 N 1 -(5-sulfonamido-1,3,4-thiadiazol-2-yl)-N 3 -O-Chlorophenylurea

[0035] A. Synthesis of intermediate 2-amino-5-sulfonamido-1,3,4-thiadiazole

[0036] Dissolve 5.0 g of acetazolamide in 60 ml of ethanol, add 6 ml of 12N hydrochloric acid solution, and heat to reflux for about 6 hours (TLC to follow up the reaction process). Ethanol was removed under reduced pressure, and a solid precipitated out. The solid was added dropwise with 1N sodium hydroxide solution in an ice-water bath until the pH was 8. The crude product was obtained by suction filtration, and the pure product was obtained by recrystallization with water. m.p=219~220°C, the yield is 75%.

[0037] B.N. 1-(5-sulfonamido-1,3,4-thiadiazol-2-yl)-N 3 -O-Chlorophenylurea

[0038] Dissolve 0.36g (2mmol) of 2-amino-5-sulfonamido-1,3,4-thiadiazole 1 in 12ml of acetonitrile, slowly add 2mmol of o-chlorophenyl isocyanate dropwise, and heat to reflux until the reaction Complete (TLC followed the pr...

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Abstract

A water-channel protein antagonist is that R1 is choosed from hydrogen, SO2NH2, C1-C4 straight chain or branched chain alkyl, R2 is choosed from phenyl, one or above halogen substituted phenyl, and X is O or S independently.

Description

Technical field: [0001] The present invention relates to a kind of aquaporin antagonist and its preparation method and application. Background technique: [0002] Water is an essential component for cells to maintain normal shape and function. In the presence of an osmotic pressure gradient, water transport in cells is mainly mediated by aquaporins (AQPs, aquaporins). Eleven subtypes of water channels have been discovered in mammals. Studies have shown that abnormal expression of aquaporins and gene mutations are closely related to certain physiological changes in the body (Verkman AS; Mitra A K. Am J Physiol Renal Physiol, 2000, 278 (1): F13-28. King L S; Yasui M; Agre P. Mol Med Today, 2000, 6(2), 60-5.), causing diseases such as nephrogenic diabetes, regulation of intraocular pressure, congestive heart failure and hearing loss. Based on this, the research on water channel antagonists is of great significance. [0003] 1,3,4-thiadiazoles have a broad spectrum of biolog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/08A61K31/433A61P35/00A61P3/10A61P13/12A61P27/02A61P27/16A61P9/04
Inventor 来鲁华刘莹邹霞娟刘振明李学军高军卫
Owner PEKING UNIV
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