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Iron feces rice-6-ketone quaternary ammonium salt and its preparation method and application

A technology of quaternary ammonium salt and iron feces, which is applied in the application field of preparing antibacterial drugs, can solve the problems of not disclosing the antibacterial activity of iron feces mi-6-ketone quaternary ammonium salt

Inactive Publication Date: 2017-11-10
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chen Meng et al. (2007) reported the iron feces rice-6-ketone isolated and purified from bitter wood and its excellent antibacterial activity; Hu Miaofen et al. (2013) reported the iron shit rice- 6-ketone and its antibacterial activity; FlorSoriano-Agato'n et al. (2005) reported the quaternary ammonium salt compound of quaternary ammonium-6-ketone isolated from Zanthoxylum bungeanum and semi-synthesized 3 ketones of ketone-6-ketone antifungal activity, but did not disclose the antibacterial activity of iron excrement rice-6-ketone quaternary ammonium salt; Kevin M.Czerwinski et al. (2005) reported the synthetic method of iron excrement rice-6-ketone, which is The large-scale preparation of 6-ketone provides the possibility; Camille Dejos et al. (2014) reported that 6-ketone can inhibit DNA replication and anti-cell proliferation

Method used

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  • Iron feces rice-6-ketone quaternary ammonium salt and its preparation method and application
  • Iron feces rice-6-ketone quaternary ammonium salt and its preparation method and application
  • Iron feces rice-6-ketone quaternary ammonium salt and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of quaternary ammonium salt (6a-u):

[0044]

[0045] Iron femin-6-one (220mg, 1mmol), potassium iodide (1.66mg, 0.01mmol), RX (5mmol), acetonitrile 20mL were mixed, stirred and reacted at 50°C, followed by TLC to detect the completion of the reaction, concentrated, and silica gel column chromatography, to obtain Target products (6a-u, as shown in Table 1).

[0046] Table 1

[0047]

[0048]

Embodiment 2

[0050] Synthesis of 3-ethyl-ironium-6-ketone-3-iodide salt (6a):

[0051] In Example 1, RX was replaced with ethyl iodide to obtain 90.24 mg of a yellow solid with a yield of 24%. m.p.>280℃; ESI-MSm / z249.08[M-I] + ; 1 H NMR (500MHz, CD 3 OD) δ: 9.01(d, J=6.0Hz, 1H), 8.68(d, J=6.3Hz, 1H), 8.56(d, J=8.2Hz, 1H), 8.47(d, J=10.2Hz, 1H ), 8.42(d, J=7.8Hz, 1H), 7.87(t, J=7.3Hz, 1H), 7.64(t, J=7.2Hz, 1H), 7.25(d, J=10.2Hz, 1H), 4.98(q,J=14.7,6.9Hz,2H),1.65(t,J=7.3Hz,3H); 13 C NMR (125MHz, CD 3 OD)δ: 157.71, 141.99, 141.13, 136.77, 134.35, 134.17, 133.95, 129.64, 129.08, 127.07, 125.13, 122.50, 119.05, 116.85, 52.81, 15.91.

Embodiment 3

[0053] Synthesis of 3-propyl-ironium-6-ketone-3-iodide salt (6b):

[0054] RX in Example 1 was replaced by iodopropane to obtain 113.04 mg of a yellow-green solid with a yield of 29%. m.p.>280℃; ESI-MS m / z263.13[M-I] + ; 1 H NMR (500MHz, CD 3 OD) δ: 9.02(d, J=6.3Hz, 1H), 8.68(d, J=6.2Hz, 1H), 8.55(d, J=8.3Hz, 1H), 8.47(d, J=10.2Hz, 1H ), 8.42(d, J=7.9Hz, 1H), 7.87(t, J=7.6Hz, 1H), 7.63(t, J=7.6Hz, 1H), 7.23(d, J=10.2Hz, 1H), 4.90(t, J=7.4Hz, 2H), 2.07-2.02(m, 2H), 1.01(t, J=7.3Hz, 3H); 13 C NMR (125MHz, CD 3 OD)δ: 157.51, 142.06, 141.42, 136.72, 134.29, 134.14, 134.03, 129.10, 128.49, 126.95, 125.07, 122.50, 118.76, 116.83, 58.44, 29.66, 9.57.

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Abstract

The invention relates to a canthium dicoccum-6-one quaternary ammonium salt and a preparation method and an application thereof. The structural formula of the compound is shown in a formula (1) in the specification, wherein R is ethyl, propyl, isopropyl, allyl, normal-butyl, isobutyl, normal-amyl, normal-octyl, unsubstituted benzyl or substituted benzyl substituted by a hydrogen atom, methyl, bromomethyl, trifluoromethyl, benzyloxyl, a fluorine atom or a chlorine atom; X is chlorine, bromine or iodine. The application is that of the compound for preparing antibacterial drugs.

Description

technical field [0001] The present invention relates to a quaternary ammonium salt of iron betamin-6-ketone, the pharmaceutical composition of this compound, and its application in the preparation of antibacterial drugs. Background technique [0002] Since the 1940s, antibiotics have been widely used clinically as antibacterial drugs. However, the targets of these antibiotics are very limited. The emergence of pathogenic bacteria cross-resistance to antibiotics makes many target sites insensitive, and the drug resistance of pathogenic bacteria is becoming more and more serious. Therefore, it is imperative to develop new antibacterial drugs. [0003] Iron betamin-6-one is a subclass of β-carboline alkaloids, which are mainly isolated from the plants of the family Aroaceae and Rutaceae. Chen Meng et al. (2007) reported the iron feces rice-6-ketone isolated and purified from bitter wood and its excellent antibacterial activity; Hu Miaofen et al. (2013) reported the iron shit ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/16A61K31/4375A61P31/04
CPCC07D471/16
Inventor 王俊儒代江坤赵菲淡文佳殷党跃高宇秦文娟张继文
Owner NORTHWEST A & F UNIV
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