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Pleuromutilin compounds with thioether side chains as well as preparation method and application of pleuromutilin compounds

A technique for pleuromutilin and compound, which is applied in the field of pleuromutilin compounds and their preparation, can solve the problem of rare drug-resistant bacteria and the like, and achieve the effect of good in vitro anti-mycoplasma activity

Active Publication Date: 2016-10-12
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]Since the mechanism of action of pleuromutilin compounds is different from that of antibiotics widely used in clinical practice, there are not many resistant bacteria to pleuromutilin antibiotics See

Method used

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  • Pleuromutilin compounds with thioether side chains as well as preparation method and application of pleuromutilin compounds
  • Pleuromutilin compounds with thioether side chains as well as preparation method and application of pleuromutilin compounds
  • Pleuromutilin compounds with thioether side chains as well as preparation method and application of pleuromutilin compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1: Synthesis of 14-O-[2-amino-1,3,4-thiadiazol-5-yl]mercaptoacetyl muulin (compound 18)

[0043] Dissolve 0.905mmol of intermediate I in 10ml of ethyl acetate, add 1.36mmol of sodium iodide and 0.905mmol of potassium carbonate, heat to reflux for 1 hour, add the alkaline solution of 2-amino-5-mercapto-1,3,4-thiadiazole , heated and stirred for 2 hours, poured the reaction solution into a separatory funnel, added chloroform for extraction, took the organic phase and evaporated to dryness, and the obtained crude product was separated and purified by silica gel column chromatography to obtain compound 18: 14-O-[2-amino -1,3,4-Thiadiazol-5-yl]mercaptoacetylmyulin. HR-MS (ESI): Calcd for C24 h 36 N 3 o 4 S 2 (M+H + ):494.2142; Found: 494.2164.

Embodiment 2

[0044] Example 2: Synthesis of 14-O-[2-(2-fluorobenzamido)-1,3,4-thiadiazol-5-yl]mercaptoacetylmyulin (compound 1)

[0045] Dissolve 1 g of compound 18 in 35 ml of ethyl acetate, add 2-fluorobenzoyl chloride equimolar to compound 18, heat and stir at 70°C for 3 h, recrystallize or purify by column chromatography to obtain the target product. The obtained reaction solution was rotary evaporated to dryness, and the mixture was redissolved in dichloromethane. After adding 1 g of 100-200 mesh silica gel for adsorption and drying, 200-300 mesh silica gel was used to pack the column under normal pressure, and the column was separated according to the solvent system determined by TLC. Compound 1 with relatively high purity was obtained with a yield of 85%. HR-MS (ESI): Calcd for C 31 h 39 FN 3 o 5 S 2 (M+H + ): 616.2310; Found: 616.2331.

Embodiment 3

[0046] Example 3: Synthesis of 14-O-[2-(3-fluorobenzamido)-1,3,4-thiadiazol-5-yl]mercaptoacetylmyulin (compound 2)

[0047] Compound 2 was obtained by the same method as described in Example 2 except that 3-fluorobenzoyl chloride was used as the starting material, and the yield was 78%. HR-MS (ESI): Calcd for C 31 h 39 FN 3 o 5 S 2 (M+H+): 616.2310; Found: 616.2330.

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Abstract

The invention discloses pleuromutilin compounds with thioether side chains as well as a preparation method and an application of the pleuromutilin compounds and belongs to the field of medicinal chemistry. The compounds have the structure shown in the formula 2 or in the formula 3, wherein R1, R2 and R3 are independently selected from hydrogen, methoxyl, methyl, hydroxy, nitryl, halogen and trichloromethyl; R is ethyl or vinyl. The pleuromutilin compounds with the thioether side chains have good activity for inhibiting mycoplasma gallisepticum and are particularly suitable for being taken as a novel antimycoplasma drug to be used for preventing and treating mycoplasma infection diseases of human beings or animals.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a pleuromutilin compound with a thioether side chain, a preparation method and application thereof. Background technique [0002] Mycoplasma was discovered by Nocard et al. in 1898. It is a prokaryotic organism without a cell wall. The only visible organelle in its cells is the ribosome. Mycoplasma can pass through bacterial filters, and its resistance to heat is similar to that of bacteria. Among human pathogenic mycoplasma, mycoplasma pneumoniae causes pneumonia, mycoplasma hominis, ureaplasma urealyticum and mycoplasma genitalium mainly cause urogenital tract infection; animal treatment mycoplasma often causes infectious diseases of livestock and poultry respiratory system in veterinary clinic. Because Mycoplasma pneumoniae has no cell wall, penicillins, cephalosporins and other antibacterial drugs acting on bacterial cell walls are ineffective. In human clinic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/135A61K31/433A61P31/04
CPCC07D285/135
Inventor 汤有志王文湘刘雅红方茜
Owner SOUTH CHINA AGRI UNIV
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