2, 4, 4-trisubstituted dihydrooxazole derivative and application thereof

A kind of dihydrooxazole, unsubstituted technology, applied in the field of drug synthesis

Active Publication Date: 2020-10-30
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although azoles play an irreplaceable role in clinical practice, the serious side effects of these drugs and the emergence of drug-resistant strains urge medicinal chemists to develop more anti-bacterial drugs with more structural types, high efficiency and low toxicity, and various delivery methods. fungal drugs

Method used

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  • 2, 4, 4-trisubstituted dihydrooxazole derivative and application thereof
  • 2, 4, 4-trisubstituted dihydrooxazole derivative and application thereof
  • 2, 4, 4-trisubstituted dihydrooxazole derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] Example 1: 4-((1H-imidazol-1-yl)methyl)-2-([1,1'-biphenyl]-4-yl)-4-methyl-4,5-dihydrooxane azole

[0125]

[0126] In step a: the raw materials 1-1 (1.1 mmol), bibenzoic acid 1-2 (1.1 mmol) and PyBOP (1H-benzotriazol-1-yloxytripyrrolidinyl hexafluorophosphate) (1.2 mmol) were combined ) was added to DMF, stirred at room temperature for 8 h, TLC detected the reaction completion, added water, extracted with ethyl acetate, washed the organic layer with saturated brine, and dried over anhydrous sodium sulfate overnight. The desiccant was filtered off and concentrated under reduced pressure to obtain Intermediate 1-3.

[0127] In step b: intermediate 1-3 (5mmol), SOCl 2 (12.5 mmol) and triethylamine (12.5 mmol) were added to dichloromethane, the reaction was stirred at room temperature, TLC detected the reaction was complete, the organic solvent was evaporated, dissolved in ethyl acetate, washed with water 3 times, the organic layer was washed with saturated NaCl, anhyd...

Embodiment 2

[0133] Example 2: 4-((1H-imidazol-1-yl)methyl)-2-([1,1'-biphenyl]-4-yl)-4-isopropyl-4,5-dihydro oxazole

[0134]

[0135] ESI-MS[M+H] + (m / z): 346.1.

Embodiment 3

[0136] Example 3: 4-((1H-imidazol-1-yl)methyl)-2-([1,1'-biphenyl]-4-yl)-4-cyclopropyl-4,5-dihydro oxazole

[0137]

[0138] ESI-MS[M+H] + (m / z): 344.1.

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Abstract

The invention belongs to the technical field of drug synthesis, and relates to 2, 4, 4-trisubstituted dihydrooxazole derivatives, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, preparation methods of the 2, 4, 4-trisubstituted dihydrooxazole derivatives and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and an application of the 2, 4, 4-trisubstituted dihydrooxazole derivatives and the prodrugs thereof as drugs for treating various diseases caused by fungal infection. The general formula of the 2, 4, 4-trisubstituted dihydrooxazole derivative and the stereoisomer or the pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof is shown as (I), wherein MBG, X, Y, M and R1 are shown in the claims and the specification. .

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and relates to a class of 2,4,4-trisubstituted dihydrooxazole derivatives and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, their preparation methods and their preparations. Use as a medicament for the treatment of various diseases caused by fungal infections. Background technique [0002] Fungal infection can be divided into superficial fungal infection and deep fungal infection, among which superficial fungal infection is mainly caused by ringworm, such as skin, hair and nail (toe) fungal infection; deep fungal infection is mainly caused by Candida albicans, Cryptophytes Cocci and Aspergillus fumigatus cause infections of deep tissues such as subcutaneous tissue and intima. In the past three decades, with the increasing number of patients with immunodeficiency, the rate of fungal infection has soared, which seriously threatens human health. It is urgent to f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/06C07D413/14A61K31/422A61K31/496A61P31/10
CPCC07D413/06C07D413/14A61P31/10
Inventor 赵冬梅赵立雨程卯生孙楠楠田霖丰孙印郑阳张储
Owner SHENYANG PHARMA UNIVERSITY
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