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Beta-azoles-phenyl ketone derivative and application thereof

A phenyl, biphenyl technology, applied in hydrates, β-azoles-phenyl ketone derivatives and their pharmaceutically acceptable salts, in the field of medicine for various diseases, can solve liver and kidney toxicity, drug- Drug interactions and drug resistance, narrow antibacterial spectrum, etc.

Active Publication Date: 2019-03-19
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, there are still some deficiencies in this class of drugs, such as narrow antibacterial spectrum, liver and kidney toxicity, drug-drug interactions and drug resistance.

Method used

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  • Beta-azoles-phenyl ketone derivative and application thereof
  • Beta-azoles-phenyl ketone derivative and application thereof
  • Beta-azoles-phenyl ketone derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Example 1: 1-(phenyl)-2-[(1,1'-biphenyl)-4-carboxamido]-3-(1H-imidazol-1-yl)-acetone

[0092]

[0093] The synthetic route is as follows:

[0094]

[0095] Reagents and conditions: (a) i) urotropine, chloroform; ii) 37% hydrochloric acid, ethanol; (b) (Boc) 2 O, sodium bicarbonate, methanol; (c) sodium bicarbonate, formaldehyde (aq), methanol; (d) TsCl, TEA, DMAP, DCM; (e) imidazole, K 2 CO 3 , DMF; (f) hydrochloric acid-ethanol; (g) tetrakistriphenylphosphopalladium, potassium carbonate, dioxane: water; (h) HOBt, EDCI, DIEA, DMF.

[0096] Add 2.0g (10.05mmol) of α-bromoacetophenone and 1.4g (10.05mmol) of urotropine into 60mL of chloroform in turn, react at 50 degrees Celsius, TLC detects that the reaction is complete, filter, filter cake, 5mL concentrated Add hydrochloric acid to 50mL ethanol, reflux for 4h, filter, and concentrate the filtrate to prepare intermediate 1-2.

[0097] Intermediate 1-2 (10.05mmol), (Boc) 2 O (15mmol) and sodium bicarbonate (22m...

Embodiment 2

[0105] Example 2: 1-(2-fluoro-phenyl)-2-[(1,1'-biphenyl)-4-carboxamido]-3-(1H-imidazol-1-yl)-acetone

[0106]

[0107] ESI-MS[M+H] + (m / z): 414.1.

[0108] 1 H NMR(600MHz,DMSO)δ9.25(d,J=7.7Hz,1H),7.81-7.78(m,1H),7.77-7.71(m,4H),7.70–7.67(m,2H),7.64– 7.58(m,2H),7.48(t,J=7.7Hz,2H),7.40(t,J=7.4Hz,1H),7.33-7.29(m,1H),7.18(s,1H),6.86(s , 1H), 5.39–5.28 (m, 1H), 4.67 (dd, J=14.2, 4.2Hz, 1H), 4.42 (dd, J=14.2, 9.5Hz, 1H).

Embodiment 3

[0109] Example 3: 1-(3-Fluoro-phenyl)-2-[(1,1'-biphenyl)-4-carboxamido]-3-(1H-imidazol-1-yl)-propanone.

[0110]

[0111] ESI-MS[M+H] + (m / z): 414.1.

[0112] 1 H NMR (600MHz, DMSO) δ9.21(d, J=8.3Hz, 1H), 7.86(d, J=7.8Hz, 1H), 7.80(d, J=8.5Hz, 2H), 7.78–7.76(m ,1H),7.74(d,J=8.5Hz,2H),7.72–7.68(m,2H),7.62(s,1H),7.59–7.55(m,1H),7.50–7.47(m,3H), 7.40(t, J=7.4Hz, 1H), 7.22(s, 1H), 6.84(s, 1H), 5.72–5.69(m, 1H), 4.60(dd, J=14.1, 4.5Hz, 1H), 4.44 (dd, J = 14.1, 9.6 Hz, 1H).

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Abstract

The invention belongs to the technical field of pharmaceutical synthesis, and provides a beta-azoles-phenyl ketone derivative shown as a general formula, stereoisomers of the beta-azoles-phenyl ketonederivative or pharmaceutically acceptable salt, hydrates, solvate or pro-drugs of the beta-azoles-phenyl ketone derivative and methods for preparing the stereoisomers or the pharmaceutically acceptable salt, the hydrates, the solvate or the pro-drugs. Definition of an A, a B, an R1, an R2, an R3 and an X is given in an instruction book. The beta-azoles-phenyl ketone derivative, the stereoisomersor the pharmaceutically acceptable salt, the hydrates, the solvate or the pro-drugs and the methods have the advantages that compounds are high in inhibitory activity for superficial and deep fungi, are high in activity, low in toxicity and broad in antibacterial spectrum as compared with clinically used antifungal drugs and can be used for preparing antifungal drugs, and the like.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and relates to a class of β-azole-phenyl ketone derivatives and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, their preparation methods and their use as a treatment for fungal infections Use in medicine for various diseases caused by infection. technical background [0002] Fungal infection is a common disease, divided into superficial fungal infection and deep fungal infection, superficial fungal infection such as skin, hair and finger (toe) nail and other fungal infections; Infect. In the past 30 years, with the development and extensive application of medical technologies such as chemotherapy and organ transplantation, more and more HIV patients, the use of immunosuppressants have increased sharply, and the fungal infection rate has soared, which seriously threatens human health. Therefore, we are looking for new Antifungal drugs are imminent. ...

Claims

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Application Information

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IPC IPC(8): C07D233/61C07D413/12C07D409/12A61P31/10A61K31/417A61K31/4178A61K31/422A61K31/4196
CPCA61P31/10C07D233/61C07D249/08C07D409/12C07D413/12
Inventor 赵冬梅赵立雨程卯生赵世振张向前孙楠楠田霖丰孙印
Owner SHENYANG PHARMA UNIVERSITY
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