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Alicyclic amine type naphthalimide metronidazole derivative and preparation method and application thereof

A technology of naphthylimide metronidazole and alicyclic amine is applied in the field of chemistry and achieves the effects of easy availability of raw materials, simple preparation method and fast sterilization speed

Active Publication Date: 2017-09-01
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, the introduction of naphthalimide into metronidazole has not been reported

Method used

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  • Alicyclic amine type naphthalimide metronidazole derivative and preparation method and application thereof
  • Alicyclic amine type naphthalimide metronidazole derivative and preparation method and application thereof
  • Alicyclic amine type naphthalimide metronidazole derivative and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1, the preparation of intermediate III

[0036]

[0037] The method described in the reference "Luo Y L, Kishore B, Kumar K V, Zhou C H, Cai G X. Novelbenzmidazole derived naphthalimide triazoles: synthesis, antimicrobial activity and interactions with calf thymus DNA. Sci. China Chem., 2015,58,483-494" 4-Bromo-1,8-naphthalene diic anhydride was prepared by reacting with ammonia water to obtain 5.08 g of intermediate III with a yield of 92.0%; brown solid.

Embodiment 2

[0038] Embodiment 2, the preparation of intermediate IV

[0039]

[0040]In a 100mL round bottom flask, add III (2.76g, 10mmol), chloroacetone (1.39g, 15mmol), potassium carbonate (1.38g, 10mmol), use DMF (dimethylformamide, 10mL) as solvent, 100°C The reaction was stirred, followed by TLC until the end of the reaction, cooled to room temperature (18-25° C.), concentrated, extracted, separated by column chromatography, and dried to obtain 2.07 g of compound IV with a yield of 62.3%.

[0041] Compound IV: white powder; melting point 220–221°C; 1 H NMR (600MHz, CDCl 3 ): δ8.64(d, J=7.1Hz, NAPH-H,1H), 8.59(d, J=8.4Hz, NAPH-H,1H), 8.40(d, J=7.8Hz, NAPH-H,1H ), 8.04(d, J=7.8Hz, NAPH-H, 1H), 7.85(t, J=7.9Hz, NAPH-H, 1H), 5.01(s, NAPH-CH 2 ,2H),2.34(s,-CH 3 ,3H)ppm.

Embodiment 3

[0042] Embodiment 3, the preparation of intermediate V

[0043]

[0044] In a 100mL round bottom flask, the intermediate IV (3.32g, 10mmol) was dissolved in (10mL) glacial acetic acid, and bromine (1.59g, 10mmol) was slowly added dropwise, and the reaction was stirred at 40°C for 30min under temperature control, Afterwards, the temperature was raised to 60°C and the reaction was stirred. TLC was followed until the end of the reaction. An aqueous solution of sodium bisulfite was added to precipitate out. After cooling, it was filtered with suction, dried, separated by column chromatography, and dried to obtain 2.16 g of compound V with a yield of 52.6%.

[0045] Compound V: white solid; melting point 223–225°C; 1 H NMR (600MHz, DMSO-d 6 ): δ8.60(dd, J=6.5, 5.6Hz, NAPH-H, 2H), 8.36(d, J=7.6Hz, NAPH-H, 1H), 8.26(d, J=7.8Hz, NAPH-H ,1H),8.04(t,J=7.9Hz,NAPH-H,1H),5.15(s,NAPH-CH 2 ,2H),4.64(s,-CH 2 Br, 2H) ppm.

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Abstract

The invention relates to an alicyclic amine type naphthalimide metronidazole derivative and a preparation method and application thereof. A structure is shown in a formula I or a formula II. The alicyclic amine type naphthalimide metronidazole derivative has the advantages that the certain inhibiting activity on gram positive bacteria, gram negative bacteria and fungi is realized; after jointly using with clinical medicines, the antibacterial activity is greatly improved; the sterilizing speed is high, the development of medicine resistance is slow, and the derivative can be used for preparing anti-bacteria and / or anti-fungi medicines, and can be used as a bacterial DNA (deoxyribonucleic acid) embedding agent; the commercial degree of preparation raw materials is high, the cost is low, the obtaining is easy, the preparation route is short, and the method is simple and convenient. The formula I or formula II is shown in the attached figure.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to alicyclic amine naphthalimide metronidazole derivatives, and also relates to a preparation method and application of alicyclic amine naphthalimide metronidazole derivatives. Background technique [0002] Metronidazole is the most popular clinical high-efficiency insecticide, and it is also one of the first-selected drugs for anaerobic bacteria. The World Health Organization (WHO) lists metronidazole as an essential drug for anti-infection. The nitro group in it is not only beneficial to tissue penetration, but also the metabolic activation of nitro group can induce biological activity. Notably, despite the long-term clinical use of metronidazole, the incidence of drug resistance remains low. Continuous research is therefore devoted to the development of novel metronidazole derivatives. However, the reactive intermediate generated by the reduction of the nitro group in metro...

Claims

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Application Information

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IPC IPC(8): C07D401/06A61P31/04A61P31/10
CPCC07D401/06Y02A50/30
Inventor 周成合康杰哥帕拉·拉瓦亚曼纳保那·拉默汉·拉奥·亚达夫
Owner SOUTHWEST UNIVERSITY
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