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Diphenyl diazole derivative, and preparation method and application thereof

A technology of biphenyldiazoles and azole derivatives, which is applied in the direction of pharmaceutical formulations, medical preparations containing active ingredients, organic active ingredients, etc., and can solve problems such as narrow antibacterial spectrum, drug resistance, and drug interactions. Achieve good antifungal and antibacterial activity, strong antibacterial activity, and good application prospects

Active Publication Date: 2019-06-07
HENAN NEWLAND PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although there are many clinically available antibacterial drugs that can have both antifungal and antibacterial effects, they all have the limitation of a single significant antibacterial effect. For example, azoles have an irreplaceable role in clinical practice, but such drugs More and more deficiencies have been exposed, such as narrow antibacterial spectrum, drug resistance, toxic and side effects, single dosage form, drug interaction, etc. The development of new broad-spectrum, high-efficiency, low-toxicity, and diverse delivery methods of antibacterial drugs has been is an important subject of research in this field

Method used

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  • Diphenyl diazole derivative, and preparation method and application thereof
  • Diphenyl diazole derivative, and preparation method and application thereof
  • Diphenyl diazole derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 N-[1-(1H-imidazol-1-yl)-3-(1H-imidazol-4-yl)prop-2-yl]-(1,1'-biphenyl)-4-carboxamide.

[0057]

[0058] Step 1 Preparation of 1,1'-biphenylcarboxylic acid (intermediate 3).

[0059] Under argon protection, 2.75g (13.8mmol) of 4-bromobenzoic acid, 2g (16.4mmol) of phenylboronic acid, K 2 CO 3 2.71g (27.3mmol) and 0.2g tetrakistriphenylphosphopalladium were added to 40mL of dioxane solvent / water (10:1), and the temperature was raised to 75°C. After 5h, the reaction was monitored by TLC. The reaction solution was cooled, filtered with suction, and the pH value was adjusted to 2-3. A large amount of white solid was formed, and 2.30 g of white solid was obtained by suction filtration, with a yield of 84.9%. MS[M+H] + (m / z): 199.2.

[0060] Step 2 Preparation of intermediate 5.

[0061] Intermediate 3 (2g, 10.1mmol), EDC·HCl 2.13g (11.1mmol) and HOBt 1.50g (11.1mmol) were dissolved in 40mL DMF, stirred at room temperature for 1h, and histidinol hydrochloride...

Embodiment 2

[0066] Example 2 N-[1-(1H-imidazol-1 base)-3-(1H-imidazol-4 base)prop-2-yl]-2'-fluoro-(1,1'-biphenyl)- 4-formamide

[0067]

[0068] LC-MS m / z[M+H] + 390.2. 1 H-NMR (600MHz, DMSO-d 6 )δ13.24(s,1H),9.04(d,J=8.0Hz,1H),8.76(s,1H),7.90(d,J=8.4Hz,2H),7.80(s,1H),7.68– 7.65(m,2H),7.63(s,1H),7.60(td,J=7.9,1.5Hz,1H),7.51–7.43(m,1H),7.36–7.33(m,2H),7.23(s, 1H), 6.87(s, 1H), 4.88(ddd, J=9.9, 8.1, 4.7Hz, 1H), 4.57(dd, J=14.1, 4.7Hz, 1H), 4.42(dd, J=14.1, 10.0Hz ,1H),2.96-2.63(m,2H).

Embodiment 3

[0069] Example 3 N-[1-(1H-imidazol-1 base)-3-(1H-imidazol-4 base)prop-2-yl]-2'-chloro-(1,1'-biphenyl)- 4-formamide

[0070]

[0071] LC-MS m / z[M+H] + 406.2. 1 H-NMR (400MHz, DMSO-d 6 )δ13.15(s, 1H), 9.01(d, J=7.9Hz, 1H), 8.74(s, 1H), 7.85(d, J=8.3Hz, 2H), 7.76(s, 1H), 7.64( s,1H),7.62–7.58(m,1H),7.55(d,J=8.4Hz,2H),7.49–7.41(m,3H),7.23(s,1H),6.86(s,1H),5.02 –4.90(m,1H),4.79–4.74(m,1H),4.41(dd,J=14.0,9.9Hz,1H),2.95-2.64(m,2H).

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Abstract

The invention belongs to the field of chemical synthesis of medicines, especially relates to a diphenyl diazole derivative and a preparation method thereof, and also relates to an application of the diazole derivative in the preparation of medicines for treating various diseases caused by fungal or bacterial infections. In-vitro antibacterial activity test of the diphenyl diazole derivative defined in the invention shows that the compound has strong antifungal and antibacterial activities, and compared with the existing antibacterial medicines, the compound has the advantages of novel structure, high efficiency and broad spectrum, so the diphenyl diazole derivative defined in the invention has an excellent application prospect.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a bibendazole derivative and a preparation method thereof. The invention also relates to the application of a diazole derivative in the preparation of medicines for treating various diseases caused by fungal or bacterial infections . Background technique [0002] Fungal infection is a common disease, which can be divided into superficial fungal infection and deep fungal infection according to the different infection sites. Among them, superficial fungal infection has a higher incidence rate, which can cause skin, nail, mucous membrane infection, etc., but generally does not lead to serious consequences; the main pathogenic bacteria of superficial fungal infection are Trichophyton, Epidermophyton, etc. . Deep fungal infection is also known as systemic fungal infection. In recent years, with the extensive use of immunosuppressants and broad-spectrum antibiotics, the incr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64C07D403/06A61K31/4178A61K31/4196A61P31/04A61P31/10
Inventor 谢建中刘超
Owner HENAN NEWLAND PHARMA
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