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N-(2,3-dihydro benzo [b] thiapyran-4-imino)-N'-(4-methyl phenyl) guanidine derivative and application thereof

A technology of methylphenyl and guanidine derivatives, applied in the field of medicine

Inactive Publication Date: 2014-04-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The N-(2,3-dihydrobenzo[b]thiopyran-4-imino)-N′-(4-methylphenyl)guanidine derivatives have not been reported so far

Method used

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  • N-(2,3-dihydro benzo [b] thiapyran-4-imino)-N'-(4-methyl phenyl) guanidine derivative and application thereof
  • N-(2,3-dihydro benzo [b] thiapyran-4-imino)-N'-(4-methyl phenyl) guanidine derivative and application thereof
  • N-(2,3-dihydro benzo [b] thiapyran-4-imino)-N'-(4-methyl phenyl) guanidine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1: Preparation of N-(6-fluoro-2,3-dihydrobenzo[b]thiopyran-4-imino)-N'-phenyl)guanidine

[0074] Add 0.5g (0.0027mol) 6-fluorothiochroman-4-one, 20mL absolute ethanol, and 2 drops of glacial acetic acid into a 50mL reaction flask, stir and heat to reflux, react for 15min, then add 4-phenylaminoguanidine hydrogen Iodate salt 0.78g (0.0028), continue to reflux for 5h, cool to room temperature, filter off the solid produced by the reaction, concentrate the filtrate under reduced pressure, and recrystallize the residue with 95% ethanol to obtain 0.3g of yellow solid, yield 35.4% , Mp: 177-178℃LC-MS(m / z): 314[M+H] + ,H-NMR(DMSO-d6)δ(ppm):9.40(2H,s,9',7'-H),8.41-8.37(1H,m,4'-H),8.16-8.11(1H,dd ,J=3.0Hz,J=2.7Hz,5-H),7.37-7.03(6H,m,Ph-H),6.68(1H,s,8-H),3.03-2.99(2H,t,J= 6.0Hz, J=6.3Hz, 2-H), 2.89-2.84, (2H, t, J=6.3Hz, J=6.0Hz, 3-H)

Embodiment 2

[0075] Example 2: Preparation of N-(6-fluoro-2,3-dihydrobenzo[b]thiopyran-4-imino)-N'-(4-methylphenyl)guanidine

[0076] Add 0.5g (0.0027mol) 6-fluorothiochroman-4-one, 20mL absolute ethanol, and 2 drops of glacial acetic acid into a 50mL reaction flask, stir and heat to reflux, react for 15min, then add 4-(4-methyl Phenyl)aminoguanidine hydroiodide 0.82g (0.0028), continue to reflux for 3.5h, cool to room temperature, filter off the solid produced by the reaction, concentrate the filtrate under reduced pressure, and recrystallize the residue with 95% ethanol to obtain a yellow solid 0.52g, yield 59.1%, Mp: 215-217°C. LC-MS(m / z):329[M+H] + ,327[M-H] + , 1 H-NMR(DMSO-d6)δ(ppm):10.60(1H,s,9'-H),9.92(1H,s,7'-H),8.46-8.44,(1H,dd,J=2.4Hz ,J=2.4Hz,5-H),7.89(1H,s,8-H)7.37-7.30(3H,t,J=2.4Hz,J=3.3Hz,Ph-H),7.27-7.26(2H, d,J=4.2Hz,Ph-H),7.20-7.18(1H,td,J=1.2Hz,J=1.2Hz,J=1.5Hz,7-H),3.16-3.14(2H,t,J= 3.0Hz,J=3.3Hz,2-H), 3.01-2.99,(2H,t,J=3.3Hz,J=3.0Hz,3-H),2.37(3H,s,4'-H).

Embodiment 3

[0077] Example 3: Preparation of N-(6-fluoro-2,3-dihydrobenzo[b]thiopyran-4-imino)-N'-(3-methylphenyl)guanidine

[0078] Add 0.5g (0.0027mol) 6-fluorothiochroman-4-one, 20mL absolute ethanol, and 2 drops of glacial acetic acid into a 50mL reaction flask, stir and heat to reflux, react for 15min, then add 4-(3-methyl Phenyl) aminoguanidine hydroiodide 0.82g (0.0028), continue to reflux for 4.5h, cool to room temperature, filter off the solid produced by the reaction, concentrate the filtrate under reduced pressure, and recrystallize the residue with 95% ethanol to obtain light yellow Powdery solid 0.44g, yield 48.3%, Mp: 179-181°C. LC-MS(m / z):329[M+H] + , 1 H-NMR(DMSO-d6)δ(ppm):10.63(1H,s,9'-H),9.90(1H,s,7'-H),7.70,(1H,s,5-H),7.89 (1H,s,8-H),7.37-7.30(3H,t,J=2.4Hz,J=3.3Hz,Ph-H),6.59-7.08(2H,d,J=4.2Hz,Ph-H) ,6.24-6.36(1H,td,J=1.2Hz,J=1.2Hz,J=1.5Hz,7-H), 3.46-3.21(2H,t,J=3.0Hz,J=3.3Hz,2-H ), 3.01-2.84, (2H,t,J=3.3Hz,J=3.0Hz,3-H),2.34(3H,s,3'-H).

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Abstract

The invention provides a novel (i) N ( / i)-(2,3-dihydro benzo [(i) b ( / i)] thiapyran-4-imino)-(i) N'-( / i)-(4-methyl phenyl) guanidine derivative, a preparation method thereof, and pharmaceutically acceptable salts thereof, and also relates to a pharmaceutical composition with the compound as an active component, and the pharmaceutical composition as an antifungal agent has a strong killing effect on clinical common pathogenic fungi, and is expected to overcome the defects of strong toxic and side effects, low tendency to produce drug resistance, and the like of azole antifungals clinically widely used in the prior art. The structural formula is as a formula I compound and the pharmaceutically acceptable salts thereof.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically it is N-(2,3-dihydrobenzo[b]thiopyran-4-imino)-N′-(4-methylphenyl) with antifungal activity ) Guanidine derivatives and pharmaceutically acceptable salts thereof. Background technique [0002] Mycosis is a multiple, refractory disease. In recent years, due to the extensive use of drugs such as antibiotics, hormones, and immunosuppressants; the widespread use of large-scale operations such as catheters, intubations, and organ transplants, fungal infections, especially deep fungal infections, have become increasingly serious. Drugs for the treatment of fungal diseases are scarce. Azole antifungal drugs are still the first choice. Although these antifungal drugs have certain curative effects, their clinical application is limited due to their obvious toxic and side effects and poor curative effect on deep fungal infections. Therefore, it is still a very meaningful work to de...

Claims

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Application Information

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IPC IPC(8): C07D335/06A61K31/382A61K31/496A61P31/10
CPCC07D335/06
Inventor 郭春苏昕梁振田野张卫军李传玲孙寰宇崔巧平韩雪徐从军焦恩强李硕
Owner SHENYANG PHARMA UNIVERSITY
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