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Adamantyl quinoline complexes, intermediates, preparation methods and applications thereof

A technology of adamantyl quinoline and complexes, which is applied in the direction of zinc organic compounds, copper organic compounds, drug combinations, etc., can solve the problems of difficult cell membrane penetration, alloantigenicity, easy hydrolysis by protease, and difficulty in SOD extraction. Achieve strong biocompatibility, strong lipophilicity and easy-to-obtain raw materials

Inactive Publication Date: 2016-03-30
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to overcome the shortcomings of natural superoxide dismutase natural SOD in the prior art, such as difficult extraction, high cost, easy to be hydrolyzed by protease, difficult to penetrate cell membrane and heterogeneous antigenicity, and provide an easy-to-prepare, A low-cost, highly efficient and easily permeable SOD mimetic enzyme with adamantane and quinoline structures, that is, an adamantyl quinoline complex, and provides a preparation method and application of the adamantyl quinoline complex, and also Provided are intermediates and preparation methods for preparing adamantyl quinoline complexes

Method used

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  • Adamantyl quinoline complexes, intermediates, preparation methods and applications thereof
  • Adamantyl quinoline complexes, intermediates, preparation methods and applications thereof
  • Adamantyl quinoline complexes, intermediates, preparation methods and applications thereof

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preparation example Construction

[0041] In the preparation method of the above intermediate, in order to increase the reaction speed of the contact reaction, the contact reaction is preferably carried out under heating, and the reaction temperature may be 81-100°C; preferably 85-90°C.

[0042] According to the present invention, in order to make the contact reaction fully proceed, preferably, the reaction time of the contact reaction may be 1-15 h, preferably 2-8 h.

[0043] The method for purifying the crude product of the intermediate obtained through the contact reaction is not particularly limited, and a relatively simple method is to perform pure crystallization of the crude product of the intermediate in absolute ethanol to obtain a pure intermediate.

[0044] The present invention also provides a preparation method for the adamantyl quinoline complex of the structure shown in formula (I) or formula (II), wherein, in the presence of an organic solvent, the Intermediates and [M(N3) 2 ]·6H 2 O, [M(N1 N2) ...

Embodiment 1-1

[0058] The preparation of the intermediate of structure shown in formula (L):

[0059]

[0060] In a 250mL round bottom flask, add 1-adamantanamine hydrochloride solid 5.0mmol, 2-chloromethyl-quinoline hydrochloride 10.05mmol and 60mL anhydrous acetonitrile solvent, and the mixture is magnetically stirred at 20°C, After dissolving, add dry 15.0mmol potassium carbonate solid, reflux at 85°C for 6 hours, cool to 20°C, remove insoluble matter by filtration, rotate the filtrate, and dissolve the obtained crude product in absolute ethanol. Color cubic crystal A1, the yield is 68%.

[0061] The above-mentioned A1 is detected, and the result of elemental analysis is C 30 h 31 N 3 : C, 83.17%; N, 9.56%; H, 7.32%; theoretically calculated values: C, 83.10%; N, 9.69%; H, 7.21%, indicating that the results of elemental analysis are consistent with the results of theoretical calculations. 1 HNMR (CDCl 3 ,300MHz): δ(ppm):7.92-7.99(m,4H,Ar-H-2,3),7.67-7.72(m,4H,Ar-H-5,6),7.60(s,2H,A...

Embodiment 1-2

[0063] The preparation of the intermediate of structure shown in formula (L):

[0064]

[0065] According to the method of Example 1-1, the difference is that the potassium carbonate is 25 mmol, and colorless cubic crystal A2 is obtained with a yield of 69%.

[0066] The above-mentioned A2 is detected, and the result of the elemental analysis is C 30 h 31 N 3 : C, 83.17%; N, 9.56%; H, 7.32%; theoretically calculated values: C, 83.10%; N, 9.69%; H, 7.21%, indicating that the results of elemental analysis are consistent with the results of theoretical calculations. 1 HNMR (CDCl 3 ,300MHz): δ(ppm):7.92-7.99(m,4H,Ar-H-2,3),7.67-7.72(m,4H,Ar-H-5,6),7.60(s,2H,Ar -H-4), 7.42-7.44 (s, 2H, Ar-H-7), 4.21 (s, 4H, CH 2 ), 2.06 (m, 3H, cycl-CH), 1.85 (m, 6H, cycl-CH 2 ), 1.62 (m,6H,cycl-CH 2 ). IR (KBrdisc, cm -1 ): 3059, 2093, 2847, 1605, 1556, 1502, 1456, 1304, 1126, 830, 740, 624.

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Abstract

The invention discloses an adamantyl quinoline complex and an intermediate as well as a preparation method and application thereof, wherein the structure of the adamantyl quinoline complex is shown by the formula (I) or the formula (II); in the formula (I), M is a divalent metal cation, and N3 is selected from a perchlorate ion, a hexafluoro-phosphate ion or a tetrafluoroborate ion; in the formula (II), M is a divalent metal cation, N1 and N2 are halogen anions. The adamantyl quinoline complex disclosed by the invention has relatively high activity for catalyzing free radical disproportionation of superoxide anions.

Description

technical field [0001] The invention relates to an adamantyl quinoline complex, an intermediate for preparing the adamantyl quinoline complex, a preparation method and application of the adamantyl quinoline complex and the intermediate. Background technique [0002] The medical community generally believes that free radicals are the main cause of human aging and neurodegenerative diseases. Modern medicine has confirmed that excess superoxide ion free radicals (O 2 · - ) can lead to human aging and diseases such as cancer, cardiovascular and cerebrovascular diseases, and amyotrophic lateral sclerosis. Superoxide dismutase (SOD) removes O 2 · - The specificity of the enzyme, known as "human body scavenger", is used in clinical medicine to treat various diseases such as Alzheimer's disease and tumors, and is also widely used in skin care products and health care products. However, the natural SOD has the disadvantages of difficult extraction, high cost, short half-life, ea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08C07F3/06C07D215/12A61P39/06
Inventor 周映华孙大亮陶骏
Owner ANHUI NORMAL UNIV
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