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Substituted 2,2-dimethylthiazolidin compound, as well as preparation method and use thereof

A technology of dimethyl thiazolidine and compound, which is applied in the directions of medical preparations containing active ingredients, organic chemistry, and drug combinations, etc., can solve the problems of poor drugability and inconvenient administration.

Inactive Publication Date: 2014-05-07
INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many drugs used for radiation protection clinically, mainly sulfur-containing compounds, estrogens, cytokines, etc., but most of them have certain side effects, and their druggability is poor and administration is inconvenient

Method used

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  • Substituted 2,2-dimethylthiazolidin compound, as well as preparation method and use thereof
  • Substituted 2,2-dimethylthiazolidin compound, as well as preparation method and use thereof
  • Substituted 2,2-dimethylthiazolidin compound, as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1: 2-chloro-1-(2,2-dimethyl-3-thiazolidinyl)ethanone

[0054] Weigh 10mmol of 2,2-dimethylthiazolidine and dissolve it in 10ml of acetone, add an appropriate amount of anhydrous sodium acetate under stirring at room temperature, add dropwise 12mmol of chloroacetyl chloride diluted with acetone under ice bath conditions, after the dropwise addition React for 2h, then gradually increase the temperature to 40°C and continue to react for 2h. After the reaction is finished, use a rotary evaporator to spin off the solvent to obtain a pink powder, and add an appropriate amount of CHCl 3 Dissolve, wash with water, dilute acid, dilute alkali and salt to get light yellow CHCl 3 solution, spin off CHCl 3 solvent to give crude product. The crude product was recrystallized with petroleum ether (60-90° C.), and the product was white needle-like crystals with a yield of 89.2%. mp66.2~67.8℃. MS: Calculated value [C7 h 12 NOSC1] + : 193.5, test value [C 7 h 12 NOSC1] +...

Embodiment 2

[0055] Example 2: 2-amino-3-[2-(2,2-dimethyl-3-thiazolidinyl)-2-oxoethylmercapto]propionic acid

[0056] Add 12mmol of L-cysteine ​​to a 100ml reaction bottle, and add 12mmol of L-cysteine ​​at 3mol / LNH 4 After 15ml of OH is dissolved, control the temperature below 3°C in an ice bath, and add dropwise 10mmol of 2-chloro-1-(2,2-dimethyl-3-thiazolidinyl) dissolved in 10mL of absolute ethanol under vigorous stirring ) ethyl ketone, maintaining the reaction temperature to continue the reaction for 4h. Then the solvent was evaporated to dryness under reduced pressure (2 O / C 2 h 5 OH recrystallized to obtain white fine needle crystals with a yield of 74.2%. mp 178.3-179.7°C. MS: Calculated value [C 10 h 18 N 2 o 3 S 2 +H] + : 279.0832, test value [C 10 h 18 N 2 o 3 S 2 +H] + : 279.0830. 1 H-NMR (300MHz, D 2 O) δppm: 3.83 (m, 2H), 3.74 (m, 1H), 3.42 (s, 2H), 2.96 (m, 4H), 1.62 (s, 6H). IR: 2977, 2909 (v as , v s CH 3 ), 1632 (v as C=O), 3273, 964 (v, γOH), ...

Embodiment 3

[0057] Example 3: 1-(2,2-Dimethyl-3-thiazolidinyl)-2-[2-(5-methoxy-3-indolyl)ethylamino]ethanone

[0058] Weigh 5.25mmol 5-methoxytryptamine and dissolve it in 20ml THF, add an appropriate amount of catalyst KI and 6mmolK 2 CO 3 , stirred and dissolved at 40°C, then 5mmol 2-chloro-1-(2,2-dimethyl-3-thiazolidinyl)ethanone dissolved in 10ml THF was added dropwise, and reacted at reflux at 70°C for 6h. After the reaction is completed, the solvent is spin-off with a rotary evaporator to obtain a gray powder, and an appropriate amount of CHCl is added 3 Dissolve, wash with water, spin off CHCl 3 Add appropriate amount of ethyl acetate and stir at 40°C, filter to obtain a gray solid, and wash the filter cake with water and ethyl acetate, respectively. The obtained crude product was recrystallized in acetone to obtain earth gray flaky crystals with a yield of 58.4%. mp 166.8-168.5°C. MS: Calculated value [C 18 h 25 N 3 o 2 S] + :347, test value [C 18 h 25 N 3 o 2 S] + ...

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PUM

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Abstract

The invention relates to a substituted 2,2-dimethylthiazolidin compound, as well as a preparation method and use thereof, and particularly discloses a compound with a general formula (I), pharmaceutically acceptable salts of the compound, a medicinal composition comprising the compound and the use of the compound in radiation protection and protection of the hematopoietic and immune system. In the general formula (I), R is selected from C1 to C6 linear and branched unsaturated alkyl substituents, preferably an allyl group, an isopentene group and 2-butenyl, can also be an aromatic base and a substituted aromatic group, preferably a benzyl group and a substituted benzyl group, and can further be a C1 to C6 linear and branched carbonyl substituent, wherein the carbonyl substituent can also be substituted by a heteroaromatic ring-containing substituent and sulphydryl-containing amino acid.

Description

technical field [0001] The present invention relates to a class of novel substituted 2,2-dimethylthiazolidine compounds, its preparation method and its use in protecting hematopoiesis, immune system and radiation protection. Background technique [0002] Ionizing radiation (X or gamma rays, neutrons, and alpha particles with sufficient energy) produces reactive free radicals in biological tissues, and these free radicals interact with key macromolecules such as DNA, proteins, or biomembranes, resulting in cell damage and even May cause cellular dysfunction and apoptosis. In recent years, with the tense nuclear safety situation in the world and the rapid development of radiotherapy, especially after the nuclear leakage accident at Fukushima Nuclear Power Plant in Japan, the research on radiation protective agents has once again aroused people's attention. The application of radioprotectants can effectively reduce the morbidity or mortality caused by ionizing radiation. At p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/04C07D417/12A61K31/426A61K31/427A61P7/00A61P37/00A61P39/00
CPCC07D277/04C07D417/12
Inventor 刘培勋于光允赵斌张浩姜明龙伟
Owner INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
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