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Substituted porphyrin gold (III) compounds with anticancer activity and preparation method thereof

An anti-cancer activity and compound technology, applied in the fields of organic chemistry, drug combination, anti-tumor drugs, etc., can solve the problems of large distance, poor targeting selectivity, high toxicity, etc., achieve good anti-cancer activity, small toxic side effects, scientific reasonable effect

Inactive Publication Date: 2011-09-14
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, gold tetraphenylporphyrin has poor targeting selectivity to cancer cells and high toxicity, so there is still a large distance between its experimental research and clinical application.

Method used

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  • Substituted porphyrin gold (III) compounds with anticancer activity and preparation method thereof
  • Substituted porphyrin gold (III) compounds with anticancer activity and preparation method thereof
  • Substituted porphyrin gold (III) compounds with anticancer activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 15

[0027] Example 15-(4-p-methoxyphenyl)-10,15,20-triphenylporphyrin gold (G1) compound and its preparation method.

[0028] Add 200mL of propionic acid, benzaldehyde (60mmol) and p-methoxybenzaldehyde (20mmol) into a 250mL round bottom flask, and heat to reflux. After mixing 5.53mL (80mmol) freshly distilled pyrrole and 10mL propionic acid, slowly add it dropwise to the propionic acid solution within 30min. Then the reaction was continued for 1 h, cooled to room temperature, a solid was precipitated, filtered, the solid was washed with methanol and hot water, and dried. 5-(4-p-methoxyphenyl)-10,15,20-triphenylporphyrin (L1) was obtained in a yield of 8.8%.

[0029] Add 5-(4-p-methoxyphenyl)-10,15,20-triphenylporphyrin (L1) (0.025mmol), potassium chloroaurate (0.07-0.08mmol), sodium acetate ( 0.25-0.35mmol) and 7.5-15.25mL glacial acetic acid, conventionally heated to reflux for 3-4h. TLC monitored until the reaction was complete. Acetic acid was distilled off in a rotary eva...

Embodiment 2

[0030] Example 2 Chlorination of 5,10,15,20-tetrakis(4-methoxycarbonyl)phenylporphyrin gold (G2) compound and its preparation method.

[0031] Add 200 mL of propionic acid and 4-methoxycarbonylbenzaldehyde (80 mmol) into a 250 mL round bottom flask, and heat to reflux. After mixing 5.53mL (80mmol) freshly distilled pyrrole and 10mL propionic acid, slowly add it dropwise to the propionic acid solution within 30min. Then the reaction was continued for 1 h, cooled to room temperature, a solid was precipitated, filtered, the solid was washed with methanol and hot water, and dried. 5,10,15,20-tetrakis(4-methoxycarbonyl)phenylporphyrin (L2) was obtained with a yield of 22.0%: mp>250°C; 1 H NMR (600MHz, CDCl 3 ), δ (ppm): -2.79 (s, 2H, inner-NH), 4.11 (s, 12H, -COOCH 3 ), 8.29 (d, J=7.8Hz, 8H, Ph-CH), 8.44 (d, J=7.8Hz, 8H, Ph-CH), 8.81 (s, 8H, Por-CH); IR(KBr): υ3425(m), 2919(w), 1724(s), 1607(w), 1435(w), 1383(w), 1277(m), 1108(m), 965(w), 803(w), 762(w)cm -1 ; UV-Vis (CH 2 Cl ...

Embodiment 3

[0033] Example 3 Chlorinated 5-(4-methoxycarbonyl)phenyl-10,15,20-triphenylporphyrin gold (G3) compound and its preparation method.

[0034] Using the method of Example 1, replace p-methoxybenzaldehyde (20mmol) with 4-methoxycarbonylbenzaldehyde (20mmol) to participate in the reaction, and obtain 5-(4-methoxycarbonyl)phenyl- 10,15,20-Triphenylporphyrin compound (L3). mp>250°C; 1 H NMR (CDCl 3 , 600MHz), δ (ppm): -2.79 (s, 2H, inner-NH), 4.11 (s, 3H, -COOCH 3 ), 7.74-7.79 (m, 9H, Ph-CH), 8.21 (d, J=6.6Hz, 6H, Ph-CH), 8.31 (d, J=7.8Hz, 2H, Ph-CH), 8.44 (d , J=7.8Hz, 2H, Ph-CH), 8.79(d, J=4.2Hz, 2H, Por-CH), 8.85(s, 6H, Por-CH); IR(KBr): υ3442(s), 3319(w), 2924(w), 2853(w), 1812(m), 1722(s), 1604(w), 1472(w), 1437(w), 1394(w), 1353(w), 1279(s), 1182(w), 1106(w), 800(m), 739(w)cm -1 ; UV-Vis (CH 2 Cl 2 ) / nm 416, 513, 548, 589, 646.

[0035] Using the method of Example 1, replace 5-(4-p-methoxyphenyl)-10 with 5-(4-methoxycarbonyl)phenyl-10,15,20-triphenylporphyrin compound...

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Abstract

The invention discloses substituted porphyrin gold (III) compounds with anticancer activity and a preparation method thereof, belonging to the technical field of medicament preparation. The preparation method comprises the following steps of: coordinating substituted tetraphenylporphyrin and gold to generate a substituted tetraphenyl porphyrin gold (III) compound; and introducing a targeting group onto a porphyrin ring to enhance the targeting selectivity of porphyrin gold, lower the toxicity of the porphyrin gold, further improve the performance of the porphyrin gold (III) compound and preserve or enhance the anticancer activity of the porphyrin gold (III) compound. As proved by in-vitro detection data of an S180 cell, the compound synthesized with the method has a remarkable suppressingfunction, the highest suppression ratio up to 92.863 percent higher than that of tetraphenyl porphyrin gold (III) serving as a lead compound and a weak suppressing function on normal cells. The preparation method is scientific and reasonable; and the prepared substituted porphyrin gold (III) compounds have high anticancer activity, a small toxic or side effect and a simple, convenient, and practical preparation process, and is suitable for industrial mass production.

Description

technical field [0001] The invention discloses substituted porphyrin gold (III) compounds with anticancer activity and a preparation method thereof, belonging to the technical field of medicine preparation. Background technique [0002] Cancer is a common disease with a high mortality rate, and its clinical treatment methods mainly include surgery, radiotherapy and chemotherapy. In antitumor chemotherapy drugs, some noble metal coordination compounds have been widely used clinically, such as cisplatin. However, like most chemotherapeutic drugs, cisplatin has poor targeting selectivity. While killing cancer cells, it also damages normal cells in the body, showing greater toxicity. [0003] Both Au(III) and Pt(II) are d 8 The electronic configuration, the planar structure of Au(III) complexes and cisplatin are similar, so it is speculated that Au(III) complexes may have anticancer activity similar to cisplatin. Existing studies have shown that tetraphenylporphyrin gold in v...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61P35/00
Inventor 陈华圣王存德许爱华杨茜孙良吴倩王龙祥
Owner YANGZHOU UNIV
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