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Preparation method of pefloxacin aldolase 4-aryl thiosemicarbazide derivative

A compound, selected technology, applied in the direction of organic chemistry, etc., can solve the problem of high preparation cost of synthetic route, and achieve the effect of economical synthesis method, high product purity and yield, and mild reaction conditions

Active Publication Date: 2021-11-30
ZHENGZHOU UNIV OF IND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]The previous synthetic route is expensive to prepare, and it is urgent to develop a new synthesis method

Method used

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  • Preparation method of pefloxacin aldolase 4-aryl thiosemicarbazide derivative
  • Preparation method of pefloxacin aldolase 4-aryl thiosemicarbazide derivative
  • Preparation method of pefloxacin aldolase 4-aryl thiosemicarbazide derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022]

[0023] Add 29.77g of the compound of formula 21 into 600ml of tetrahydrofuran, stir to dissolve, pass through nitrogen protection, cool down to about 10°C, control the temperature at 0-20°C, add 7.97g of borane dimethyl sulfide complex dropwise, and keep warm for 8 -9 hours. After the reaction is complete, slowly add 10 ml of water, concentrate under reduced pressure to recover the reaction solvent, and the residue is the compound of formula 3. Take a small amount of compound of formula 3, carry out mass spectrometry analysis, MS:ESI, m / z:256.05 (100.0%), 258.04 (32.1%), M+H + .

Embodiment 2

[0025]

[0026] Add 29.77g of the compound of formula 21 into 600ml of tetrahydrofuran, stir to dissolve, pass through nitrogen protection, cool down to about 10°C, control the temperature at 0-20°C, add 7.97g of borane dimethyl sulfide complex dropwise, and keep warm for 8 -9 hours. After the reaction is complete, add 26.95 g of pyridinium chlorochromate, stir and react for 5-6 hours, after the reaction is complete, recover the solvent under reduced pressure, add 100 ml of water to the residue, extract twice with 100 ml of dichloromethane, and use anhydrous sodium sulfate for the organic layer After drying, it was concentrated to dryness under reduced pressure to obtain the crude compound of formula 4, which was recrystallized and purified with isopropanol to obtain 22.58 g of the compound of formula 4. 1 HNMR (400MHz, d 6 DMSO): 1.46(t,3H), 4.52(q,2H), 8.94(s,1H), 7.02(d,1H), 7.34(d,1H), 10.4(d,1H). MS: ESI, m / z, 254.03 (100.0%), 256.03 (32.1%), M+H + .

Embodiment 3

[0028]

[0029] Add the compound of formula 4 (25.37g) into dehydrated ethanol (500ml), add 4-(4-methylphenyl)thiosemicarbazide (18.13g) shown in formula 51, reflux for 6 hours, and distill off the solvent under reduced pressure , the remaining solid was recrystallized from a mixed solvent of DMF-ethanol (V:V=4:3) to obtain 35.14 g of the compound of formula 61.

[0030] MS:ESI,m / z,417.09,M+H + ; HNMR (400MHz, DMSOd 6 ): 11.73(s,1H,CH=N),9.82(s,1H,NH),8.91(s,1H,2-H),8.45(s,1H,NH),7.81~7.03(m,6H, Ph-H, 5-H and8-H), 4.56(q, 2H, 1-NCH 2 ), 2.26(s,3H,), 1.41(t,3H).

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Abstract

The invention relates to a preparation method of a pefloxacin aldolase 4-aryl thiosemicarbazide derivative. The preparation method comprises the following steps: taking a compound in a formula 2 as an initial raw material, reducing, oxidizing, condensing with a 4-aryl thiosemicarbazide derivative, and substituting to obtain the pefloxacin aldolase 4-aryl thiosemicarbazide derivative in a formula 1. The invention provides the novel preparation method of the pefloxacin aldolase 4-aryl thiosemicarbazide derivative, and the method is mild in reaction condition, economical in synthesis method, high in product yield and suitable for commercial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of pefloxacin aldehyde 4-arylthiosemicarbazide derivatives. Background technique [0002] The innovation of new drugs originates from the discovery of leads, and the construction of lead molecules based on the combination of dominant pharmacophore skeletons is the most economical and effective strategy. The thiosemicarbazone derivatives constructed from aldehydes or ketones and thiosemicarbazides have attracted much attention because they are easy to form complexes or chelate with macromolecules or metal ions, and exhibit a wide range of pharmacological activities. However, most of the aldehydes or ketones used to construct thiosemicarbazone molecules are common benzenes or heterocyclic aromatic aldehydes and ketones, while quinoline aldehydes, especially thiosemicarbazones formed by fluoroquinolinone aldehydes, are currently Not yet reported. On t...

Claims

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Application Information

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IPC IPC(8): C07D215/38
CPCC07D215/38
Inventor 颜国华高鹏马霄王丽君崔美英
Owner ZHENGZHOU UNIV OF IND TECH