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Alicyclic amine naphthalimide metronidazole derivatives and preparation method and application thereof
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A technology of naphthylimide metronidazole and alicyclic amine is applied in the chemical field to achieve the effects of fast sterilization speed, improved antibacterial effect and simple preparation method
Active Publication Date: 2019-10-22
SOUTHWEST UNIV
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But so far, the introduction of naphthalimide into metronidazole has not been reported
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Embodiment 1
[0035] Example 1. Preparation of Intermediate III
[0036]
[0037] Reference "Luo YL, Kishore B, Kumar KV, Zhou CH, Cai G X. Novelbenzimidazole derived naphthalimide triazoles: synthesis, antimicrobial activity and interactions with calf thymus DNA. Sci. China Chem., 2015, 58, 483-494" 4-bromo-1,8-naphthalene dioic acid anhydride is prepared by reacting with ammonia to obtain 5.08 g of Intermediate III with a yield of 92.0%; a brown solid.
[0041] Compound IV: white powder; melting point 220-221℃; 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] Example 3. Preparation of Intermediate V
[0043]
[0044] In a 100mL round-bottom flask, dissolve Intermediate IV (3.32g, 10mmol) in (10mL) glacial acetic acid, and slowly add (1.59g, 10mmol) bromine dropwise, stir and react for 30min at 40°C under temperature control Then, the temperature was raised to 60° C. and the reaction was stirred. TLC tracked until the reaction was completed. An aqueous sodiumbisulfite solution was added to precipitate out. After cooling, suction filtration, drying, column chromatography separation, and drying yielded 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 specifically 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 clinically effective anti-insectdrug, and it is also one of the preferred drugs for anaerobic bacteria. The World Health Organization (WHO) lists metronidazole as a basic anti-infective drug. The nitro group not only facilitates tissue penetration, but also the metabolic activation of the nitro group can induce biological activity. It is worth noting that despite the long-term clinical use of metronidazole, the incidence of drug resistance is still very low. Therefore, continuous research is devoted to the development of new metronidazole derivatives. However, the reactive intermediate generated by the reduction of the nitro group in metronidazo...
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