A kind of phenylimidazole o-phenanthroline oleocanthin platinum complex and preparation method thereof
A technology of phenanthroline hypocretin platinum and hypocrellin, which is applied in the field of phenylimidazole o-phenanthroline hypocretin platinum complex and its preparation, and the synthesis of platinum metal complexes, which can solve the problem of toxicity Side reactions, poor selectivity and other problems, to achieve the effect of high reaction yield, simple and easy preparation method, high fluorescence quantum yield
Inactive Publication Date: 2016-04-27
NORTHWESTERN POLYTECHNICAL UNIV
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[0004] Platinum metal complexes are an important antitumor drug. Platinum anticancer drugs targeting DNA have played a huge role in the clinical treatment of cancer. Poor selectivity, easy to cause severe toxic side effects
Method used
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[0022] Preparation of PPIP
[0023]
[0024] Add 0.2g o-phenanthroline dione, 0.113mL p-tolualdehyde, 0.103mL aniline, 5mL glacial acetic acid, 0.88g ammonium acetate into a 100mL schlenk bottle. Reflux reaction for 5-24h. Add the reaction solution dropwise to the base solution and 50mL of chloroform, adjust the pH value of the solution to about 7. Extract after standing still. Extract the aqueous layer twice with chloroform, and wash the combined chloroform layer with water twice. Tetrahydrofuran was used as the eluent for chromatographic column separation to obtain 0.298 g of a light yellow solid with a yield of 81.2%. 1 HNMR (CDCl 3 ,400MHz)δ(ppm):9.190-9.139(m,2H),9.031-9.042(m,1H),7.731-7.762(m,1H),7.617-7.676(m,3H),7.518-7.535(d, 2),7.415-7.476(m,3H),7.260-7.292(m,1H),7.102-7.122(d,2),2.333(s,3H).MS(ESI + ):found386.2;calcd.for[C 26 h 18 N 4 ] / z386.1.
[0025] Preparation of PPIP-Pt-Cl 2
[0026]
[0027] Add 0.14gPPIP (1eq), 10mL anhydrous N,N-dimethylfor...
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The invention relates to a phenyl imidazole phenanthroline hypocrellin platinum complex and a preparation method thereof. The preparation method comprises the steps of adding phenanthroline dione, p-methyl benzaldehyde, aniline, glacial acetic acid and ammonium acetate into a schlenk flask, performing reflux reaction to obtain phenyl imidazole phenanthroline, adding phenyl imidazole phenanthroline, potassium tetrachloroplatinate and anhydrous N, N-dimethylformamide into the schlenk flask, performing reflux reaction to obtain PPIP-Pt-Cl2; adding PPIP-Pt-Cl2, anhydrous DMF (dimethylformamide) and a silver trifluoro-sulfonate solution into a reaction flask of the schlenk flask for reacting, then adding hypocrellin, methanol and a reducing agent, and performing reflux reaction to obtain (PPIP) 2-Pt2-HA. The preparation method is simple and easy to operate, and the reaction yield is high. The platinum complex has certain interaction with a G-quadruplex. The phenyl imidazole phenanthroline hypocrellin platinum complex provided by the invention has good interaction with G-quadruplex. The complex has relatively high fluorescence quantum yield (0.91). A fluorescence displacement experiment of the G-quadruplex proves that the G4DC50 value can achieve 0.18mu mol / L.
Description
technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a phenylimidazole-phenanthroline hypocretin platinum complex and a preparation method thereof, in particular to the synthesis of platinum metal complexes and their application in the fields of anticancer drugs and fluorescence diagnosis Applications. Background technique [0002] The G-quadruplex structure is a special DNA structure in which the G bases are connected by Hoogsteen hydrogen bonds to form a G-tetrad, and further piled up. The G-quadruplex structure can inhibit the expression of telomerase activity and also It hinders the normal recognition of telomere-related proteins to their target molecules, thereby promoting the death of tumor cells. Therefore, compounds that can recognize and stabilize the G-quadruplex structure are potential anticancer drugs. [0003] A complex is a metal-organic supramolecule formed by the coordination of multidentate ligands and met...
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IPC IPC(8): C07F15/00C09K11/06
Inventor 欧植泽陈晨高云燕曹璐刘桂霞李慧珍
Owner NORTHWESTERN POLYTECHNICAL UNIV