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Application of isatin analogs in the preparation of antitumor drugs

A technology of anti-tumor drugs and analogues, which is applied in anti-tumor drugs, drug combinations, pharmaceutical formulations, etc., and can solve problems such as research on the anti-tumor activity of isatin analogues that have not been seen

Active Publication Date: 2020-07-31
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, Chinese patent application CN201710735866.0 disclosed isatin azole compounds and their preparation methods and applications, and found that isatin azoles have certain antibacterial effects, but there is no Chinese patent on the antitumor activity of isatin analogues.

Method used

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  • Application of isatin analogs in the preparation of antitumor drugs
  • Application of isatin analogs in the preparation of antitumor drugs
  • Application of isatin analogs in the preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The synthesis of embodiment 1 compound

[0031] (1) General synthetic steps of compound 2

[0032] To a solution of chloral hydrate (2 g, 16.5 mmol) in water (30 mL) was added anhydrous sodium sulfate (13 g, 91 mmol) under stirring. After stirring at 35°C, aniline (10 mmol), concentrated hydrochloric acid (1.2 mL) and hydroxylamine hydrochloride (2.5 g, 37 mmol) were added sequentially. The mixture was further stirred at 80°C for 2 hours. After 1 hour, the mixture was cooled to 60°C, during which time a precipitate formed. After filtering and washing with water, the crude product was used in the next reaction without purification.

[0033] (2) General synthetic steps of compound 3

[0034] While stirring, concentrated sulfuric acid (30ml) was added to the solution of compound 2 (1g, 6.1mmol), and the mixture was stirred at 60-65°C for 30 minutes, and then the reaction was stirred at 80°C for 30 minutes. After 30 minutes, the mixture was cooled to 70 °C and ice wate...

Embodiment 2

[0062] In vitro inhibitory activity of embodiment 2 isatin analogs on tumor cells

[0063] NCI-H460, SGC-7901 and BGC-823 cells were seeded in 96-well plates at 4000 cells per well for 24 hours. After the tumor cells were incubated with different concentrations of compounds (60, 20, 20 / 3, 20 / 9, 20 / 27 μM) for 72 hours, the MTT solution (5 mg / mL) prepared in phosphate buffered saline (PBS) was incubated at 37 °C Cells in each well were added and treated for an additional 4 hours. Then the MTT was aspirated, and 150 μL of DMSO was added to each well, shaken for 10 minutes, and finally the OD value was measured with a microplate reader (SpectraMax M2 / M2e, Molecular Devices, Sunnyvale, USA) at a wavelength of 490 nm. The percentage of drug growth inhibition was calculated by comparison with the solvent group. Calculate the IC of each compound by GraphPad Pro 5.0 50 Value (SanDiego, CA), the results see figure 2 .

Embodiment 3

[0064] Example 3 6a Colony Formation Experiment in NCI-H460 Cells

[0065] NCI-H460 cells were seeded into 6-well plates at a density of 1000 cells / well for 24 hours and treated with 6a, curcumin, xanthohumol and blank (DMSO) for 18 hours. Replace the medium with fresh RPMI 1640 medium, aspirate the medium, wash twice with PBS, fix with 4% paraformaldehyde for 15 minutes, wash 3 times with PBS, and finally stain with crystal violet for 15 minutes, wash twice with PBS , see the result image 3 (A) ~ (C).

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Abstract

The invention belongs to the field of medicinal chemistry, and in particular relates to an application of isatin analogues in preparing antineoplastic drugs. A series of isatin analogues can be synthesized by splicing isatin and [alpha],[beta]-unsaturated ketone via a medicinal chemistry splicing principle. The compounds (the isatin analogues) are relatively good in inhibitory activity on three tumor cells, and an antineoplastic effect can be achieved by inhibiting growth and migration of tumor cells and by blocking cell cycle G2 / M period; and based upon in vivo experimental results, it is also indicated that the compounds can inhibit tumor growth.

Description

Technical field: [0001] The invention belongs to the field of medicinal chemistry. Specifically, the invention relates to the application of isatin analogues in antitumor drugs. and antitumor effects in vivo. Background technique: [0002] Chemotherapy is still the main way to treat tumors at present, but due to the toxic side effects and poor tolerance of chemotherapy drugs, their use in cancer patients is limited. Therefore, finding effective, unexplored chemotherapeutic drugs remains a great challenge. Active natural products are still an important way to discover new drugs because of their less toxic and side effects. Isatin is an endogenous substance in the human body, which has various biological activities such as anti-oxidation, anti-inflammation, and anti-tumor. Studies have shown that drug molecules containing isatin fragments have strong anti-tumor activity. For example, the drugs SU5416 and SU11248 containing isatin fragments approved by the US Food and Drug A...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/404A61P35/00C07D209/34
CPCA61K31/404C07D209/34
Inventor 李物兰汪佳兵仇佩虹云迪吴建章徐海能周晓鸥于翠娟
Owner WENZHOU MEDICAL UNIV
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