Isatin imidazole compounds as well as preparation method and application thereof

An azole compound and compound technology, applied in the field of chemical synthesis, can solve problems such as the failure of antibiotics and synthetic drugs, and achieve the effect of solving drug resistance

Inactive Publication Date: 2017-11-28
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the over-reliance on these antimicrobial drugs has led to the emergence of some multidrug-resistant bacteria, such as methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, and vancomycin-resistant Enterococcus faecium, making many traditional of antibiotics and synthetic drugs fail

Method used

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  • Isatin imidazole compounds as well as preparation method and application thereof
  • Isatin imidazole compounds as well as preparation method and application thereof
  • Isatin imidazole compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, the preparation of compound VII

[0037]

[0038] Sodium hydride (1.20g, 51mmol) and isatin (5.00g, 34mmol) were added to a 250mL round-bottomed flask, and N,N-dimethylformamide (100mL) was used as solvent, stirred at 0°C for 5 minutes, slowly 1,2-Dibromoethane (4.30mL, 51mmol) was added dropwise, reacted at 60°C under nitrogen protection, followed by TLC until the reaction was completed. Ice water was added to precipitate an orange solid, which was dried and purified to obtain compound VII (6.10 g), with a yield of 70.9%.

Embodiment 2

[0039] Embodiment 2, the preparation of compound I-1

[0040]

[0041]Add 2-methyl-5-nitroimidazole (1.27g, 10mmol) and potassium carbonate (0.75g, 5.5mmol) into a 50mL round-bottomed flask, stir with 20mL acetonitrile at 60°C for 1 hour, then add isatin Derivative VII (1.27g, 5mmol), continued to stir the reaction at 60°C, followed by TLC until the end of the reaction. Acetonitrile was distilled off under reduced pressure, then extracted with water and ethyl acetate, and then concentrated, recrystallized, dried and other post-treatments to obtain compound I-1 (0.86g), with a yield of 57.3%; yellow solid; melting point: 196–198°C . 1 H NMR (600MHz, DMSO-d 6 ,ppm): δ8.40(s,1H,Im-H-4),7.61(t,J=7.7Hz,1H,isatin-H-6),7.56(d,J=7.3Hz,1H,isatin- H-4), 7.12(t, J=7.4Hz, 1H, isatin-H-5), 7.02(d, J=7.9Hz, 1H, isatin-H-7), 4.28(t, J=5.8Hz, 2H, Im-CH 2 ), 4.07(t, J=5.8Hz, 2H, Im-CH 2 CH 2 ),2.34(s,3H,Im-CH 3 ).

Embodiment 3

[0042] Embodiment 3, the preparation of compound 1-2

[0043]

[0044] Add 4-nitroimidazole (1.13g, 10mmol) and potassium carbonate (0.75g, 5.5mmol) into a 50mL round-bottomed flask, use 20mL of acetonitrile as solvent and stir at 60°C for 1 hour, then add isatin derivative VII (1.27 g, 5mmol), continue to stir the reaction at 60°C, and follow the thin layer chromatography until the end of the reaction. Acetonitrile was distilled off under reduced pressure, then extracted with water and ethyl acetate, and then concentrated, recrystallized, dried and other post-treatments to obtain compound I-2 (0.77g), with a yield of 53.8%; yellow solid; melting point: 190–192°C . 1 HNMR (600MHz, DMSO-d 6 ,ppm):δ8.54(s,1H,Im-H-5),7.90(s,1H,Im-H-3),7.57-7.53(m,2H,isatin-H-4,isatin-H- 6), 7.11(t, J=7.5Hz, 1H, isatin-H-5), 6.92(d, J=7.9Hz, 1H, isatin-H-7), 4.35(t, J=5.5Hz, 2H, Im-CH 2 ), 4.10(t, J=5.5Hz, 2H, Im-CH 2 CH 2 ).

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Abstract

The invention relates to an isatin imidazole compound as well as a preparation method and application thereof. The isatin compounds are shown as general formulaa I-VI. The compounds have a certain inhibitory activities on Gram-positive bacteria, Gram-negative bacteria and fungi, can be used for preparing antibacterial and/or antifungal drugs, can serve as DNA intercalative agents, are simple in preparative raw materials, cheap, readily available and short in synthetic route and have significance in application of infection resistance. The structural formula is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, relates to isatin azole compounds, and also relates to the preparation method and application of the compounds. Background technique [0002] Microbial infection has become the greatest threat to human health, and about 50,000 people die from microbial infection in the world every day. So far, a large number of antibiotics and synthetic drugs have been used to treat microbial infections. However, the over-reliance on these antimicrobial drugs has led to the emergence of some multidrug-resistant bacteria, such as methicillin-resistant Staphylococcus aureus, methicillin-resistant Staphylococcus epidermidis, and vancomycin-resistant Enterococcus faecium, making many traditional Antibiotics and synthetic drugs are ineffective. Therefore, the development of antibacterial drugs with new structures has become very urgent, especially the research and development of some antibacterial drugs with high e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06A61P31/04A61P31/10
CPCC07D403/06A61P31/04A61P31/10C12Q1/68C12Q2563/173Y02A50/30
Inventor 周成合坦咖丹初·维加库玛·瑞迪张园
Owner SOUTHWEST UNIVERSITY
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