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Asymmetric multi-substituted porphyrin gold (iii) anticancer compound and preparation method thereof

A multi-substitution and asymmetric technology, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of poor targeting selectivity and large distance of cancer cells

Inactive Publication Date: 2011-12-07
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies have shown that [AuIII(TPP)]Cl has poor targeting selectivity to cancer cells, so there is still a large distance between its experimental research and clinical application.

Method used

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  • Asymmetric multi-substituted porphyrin gold (iii) anticancer compound and preparation method thereof
  • Asymmetric multi-substituted porphyrin gold (iii) anticancer compound and preparation method thereof
  • Asymmetric multi-substituted porphyrin gold (iii) anticancer compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Chloride 5-(4-methoxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin gold (4a) compound and its preparation method.

[0032] Add 200 mL of propionic acid, p-tolualdehyde (7.2 g, 60 mmol) and p-methoxybenzaldehyde (2.7 g, 20 mmol) into a 250 mL round bottom flask, and heat to reflux. Freshly distilled pyrrole (5.53 mL, 80 mmol) and 10 mL of propionic acid were mixed, and slowly added dropwise to the propionic acid solution within 30 min. 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-Methoxyphenyl)-10,15,20-tris(4-methylphenyl)porphyrin (1a) (1.47 g) was obtained in 9.5% yield: 1 H NMR (CDCl 3 , 600MHz), δ (ppm): 8.85 (s, 8H, Por-CH), 8.13-8.12 (m, 8H, Ar-CH), 7.55 (d, J=7.2Hz, 6H, Ar-CH), 7.28 (d, J=7.2Hz, 2H, Ar-CH), 4.10(s, 3H, O-CH 3 ), 2.70(s, 9H, -CH 3 ), -2.77(s, 2H, inner-NH); IR(KBr): 3021, 2914, 2857, 1605, 1505, 1467, 1346, ...

Embodiment 2

[0040] Example 2 Chloride 5-(4-methoxyphenyl)-10,15,20-tris(4-bromophenyl)porphyrin gold (4b) compound and its preparation method.

[0041] Add 200 mL of propionic acid, p-bromobenzaldehyde (11.1 g, 60 mmol) and p-methoxybenzaldehyde (2.7 g, 20 mmol) into a 250 mL round bottom flask, and heat to reflux. Freshly distilled pyrrole (5.53 mL, 80 mmol) and 10 mL of propionic acid were mixed, and slowly added dropwise to the propionic acid solution within 30 min. Then continue to react for 1.5h, cool to room temperature, precipitate solid, filter, and wash solid with methanol and hot water respectively, and dry. 5-(4-Methoxyphenyl)-10,15,20-tris(4-bromophenyl)porphyrin (1b) (1.64 g) was obtained in 8.6% yield: 2922, 2853, 1603, 1506 , 1469, 1345, 1244, 1172, 1010, 963, 798, 732, 591cm -1 ; 1 H NMR (CDCl 3 , 600MHz): δ(ppm): 8.83(s, 2H, Por-CH), 8.76(s, 6H, Por-CH), 8.04(d, J=7.8Hz, 2H, Ar-CH), 8.0(d , J=7.2Hz, 6H, Ar-CH), 7.83(d, J=7.2Hz, 6H, Ar-CH), 7.23(d, J=7.8Hz, 2H, Ar-CH)...

Embodiment 3

[0049] Example 3 Chloride 5-(4-methoxycarbonylphenyl)-10,15,20-tris(4-methoxyphenyl)porphyrin gold (4c) compound and its preparation method.

[0050] Add 200 mL of propionic acid, methyl p-formylbenzoate (3.2 g, 20 mmol) and p-methoxybenzaldehyde (8.1 g, 60 mmol) into a 250 mL round bottom flask, and heat to reflux. Freshly distilled pyrrole (5.53 mL, 80 mmol) and 10 mL of propionic acid were mixed, and slowly added dropwise to the propionic acid solution within 30 min. Then continue to react for 2h, cool to room temperature, precipitate solid, filter, and wash solid with methanol and hot water respectively, and dry. 5-(4-Methoxycarbonylphenyl)-10,15,20-tris(4-methoxyphenyl)porphyrin (1c) (1.58 g) was obtained in 9.5% yield: 1 H NMR (CDCl 3 , 600MHz) δ (ppm): 8.88 (s, 8H, Por-CH), 8.14 (d, J=7.2Hz, 2H, Ar-CH), 8.05 (d, J=6.6Hz, 6H, Ar-CH) , 7.22(d, J=6.0Hz, 2H, Ar-CH), 4.05(s, 9H, CH 3 ), 2.42(s, 3H, O-CH 3 ), -2.84 (s, 2H, inner-NH); IR (KBr): 2955, 2925, 2855, 1752, 160...

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Abstract

The invention discloses an unsymmetrical poly-substituted porphyrin gold (III) type anticancer compound and a preparation method thereof, belonging to the technical field of preparation of medicaments. The preparation method comprises the following steps of: making unsymmetrical poly-substituted porphyrin serving as a ligand react with potassium chloroaurate in an acetic acid system; and performing ion exchange through lithium chloride to obtain the anticancer compound. In the preparation method, different high-polarity radicals are introduced into a porphyrin ring, so that the symmetrical characteristic of molecules is improved, the targeting effect of a poly-substituted tetraphenyl chloride porphyrin gold compound on cancer cells is enhanced, and the dissolving capacity of the compound in water can be facilitated. The compound synthesized with the method has a remarkable inhibiting effect on SGC-7901 and SMMC-7721 tumor cells in vitro and is superior to cis-platinum serving as a positive control medicament, the highest inhibiting rates of 4c and 4a are higher than a pilot compound G0, the IC50 of 4a is less than G0, and higher targeting selectivity is shown. The unsymmetrical poly-substituted porphyrin gold (III) type anticancer compound prepared with the method has high anti-cancer activity, small toxic or side effect and simple, convenient and practicable preparation process, and is suitable for industrial production.

Description

technical field [0001] The invention discloses an asymmetric multi-substituted porphyrin gold (III) anticancer compound 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 inhibiting cancer cells, it also damages normal cells in the body, showing greater toxicity. [0003] It has been reported that Zhiming et al. have found that tetraphenylporphyrin gold chloride (III)-[AuIII(TPP)]Cl is not only simple in structure, but also very stable under physiological conditions. Oral cancer cells KB-3-1, cervical cancer cells HeLa, leukemia HL-60, nasopharynge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61P35/00
Inventor 王存德陈华圣许爱华张宗磊刘金良李艳陈颖茅蕾蕾
Owner YANGZHOU UNIV
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