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Picolinamide rhodium complex as well as synthesis method and application thereof

The technology of a pyridine amide rhodium and its synthesis method is applied in the field of medicine, which can solve the problems of unseen pyridine amide derivative rhodium complex synthesis and application, unsatisfactory anti-tumor activity, etc., and achieve high yield, easy availability of raw materials, and synthesis simple route effect

Pending Publication Date: 2022-01-18
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention also tested the in vitro inhibitory activity of pyridine amide compounds on various tumor cell lines, but the results showed that their antitumor activity was not satisfactory
[0004] There are no relevant reports on the synthesis and application of pyridine amide derivatives containing pyrazole substituent units and rhodium complexes using them as ligands.

Method used

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  • Picolinamide rhodium complex as well as synthesis method and application thereof
  • Picolinamide rhodium complex as well as synthesis method and application thereof
  • Picolinamide rhodium complex as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1: Preparation of pyridine amide derivatives (also referred to as ligands in this application) shown in formula (I)

[0058] Prepare according to the following route:

[0059]

[0060] Ia: R 1 = R 2 =CH 3 , R 3 = H;

[0061] Ib:R 1 = R 2 =CH(CH 3 ) 2 , R 3 = H;

[0062] Ic:R 1 = R 2 = CF 3 , R 3 = H;

[0063] Id: R 1 = R 2 =CH 3 , R 3 =(CH 2 ) 3 CH 3 ;

[0064] Ie: R 2 = CF 3 , R 3 = H;

[0065] If: R 2 = CF 3 , R 3 = H;

[0066] Ig: R 3 = H;

[0067] Ih: R 2 =CH 3 , R 3 =H.

[0068] Reaction solvent and condition: i) SOCl 2 , DMF, 85℃, 3h; ii) aniline, CH 3 CN, triethylamine, 80°C, 6h; iii) hydrazine hydrate, ethanol, 80°C; iv) ethanol, 90°C.

[0069] Concrete preparation method is as follows:

[0070] 1) Preparation of compound S2: Add 0.2-0.5 mL of DMF to a mixture of equimolar amounts of 3,6-dichloropicolinic acid (1.9100 g, 10.00 mmol) and thionyl chloride 2 (1.1900 g, 10.00 mmol) Catalyst, heated at 85...

Embodiment 2

[0082] Embodiment 2: the preparation of ligand

[0083] 1. Preparation of ligand Ia: Repeat Example 1, the difference is,

[0084] In step 1), the reaction is carried out at 50°C, and the reaction time is controlled at 6h;

[0085] In step 2), the reaction is carried out at 70° C., the reaction time is controlled at 8 hours, and the amount of triethylamine added is to control the pH of the system=9.5.

[0086] Finally, a white solid powder was obtained.

[0087] Carry out respectively to the powder obtained in this implementation 1 H nuclear magnetic resonance spectrum, elemental analysis and electrospray mass spectrometry and other analyzes confirmed that the obtained powder was ligand Ia.

[0088] ② preparation of ligand Ib: repeat Example 1, the difference is,

[0089] In step 3), the reaction is changed to 70°C, and the reaction time is controlled at 10h;

[0090] In step 4), methanol is used as a solvent, and the reaction is carried out at 95° C. instead.

[0091] F...

Embodiment 3

[0102] Example 3: Complex 1 (i.e. Rh(Ia)Cl 3 ·CH 3 OH) preparation

[0103] Weigh 0.025mmol ligand Ia and 0.056mmol RhCl 3 ·3H 2 O In a 50mL round-bottomed flask, add 8mL of mixed solvent (composed of chloroform and methanol at a volume ratio of 3:1), react at 80°C for 24h, filter the reacted feed liquid, and slowly volatilize the filtrate at room temperature for 3~ After 5 days, reddish-brown lumpy crystals were precipitated in the flask, and the crystals were collected and dried. Yield: 65%.

[0104] The structure was determined by methods such as single crystal X-ray diffraction analysis, and the specific characterization data are as follows:

[0105] HRMS (ESI) C 18 h 18 Cl 3 N 4 o 2 Rh[M-Cl-CH 3 OH] + Theoretical value of m / z: 462.9600; experimental value, 462.9588. Elemental analysis: theoretical value C, 40.67; H, 3.41; N, 10.54. Experimental value C, 40.63; H, 3.43; N, 10.57.

[0106] Select reddish-brown bulk crystals of moderate size and place them on an ...

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Abstract

The invention discloses a series of picolinamide rhodium complexes as well as a synthesis method and application thereof. The picolinamide rhodium complex is prepared by heating and reacting a picolinamide derivative containing a pyrazole substitution unit and rhodium trichloride in a mixed solvent composed of chloroform and methanol or acetonitrile and methanol. The synthesis route is simple, raw materials are easy to obtain, and the yield is high. Test results of the applicant show that the complexes have a remarkable anti-proliferation effect on various tumor cell strains, the activity of most complexes is remarkably higher than that of cis-platinum, and the complexes are expected to be developed into anti-tumor drugs.

Description

technical field [0001] The invention relates to a rhodium pyridine amide complex and a synthesis method and application thereof, belonging to the technical field of medicine. Background technique [0002] Pyrazole, a five-membered simple aromatic ring consisting of two nitrogen atoms in adjacent positions. Pyrazole rings are widely used in agricultural production, and pyrazole compounds have excellent insecticidal and acaricidal activities, so pyrazole heterocyclic rings are widely introduced into pesticide compound molecules. For example, the invention patent with the publication number CN110467599A discloses a pyrazole amide containing a substituted pyridine unit, which is obtained by condensation of a pyrazole acid chloride intermediate and a substituent picolylamine. The invention points out that the pyrazole amide containing substituted pyridine units has effective control effect on harmful insects and can be used to prepare insecticides in fields such as agriculture a...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61K31/555A61P35/00
CPCC07F15/008A61P35/00
Inventor 顾运琼
Owner GUANGXI NORMAL UNIV
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