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Anti-skin tumor compound and application thereof

A technology of skin tumors and compounds, applied in the field of anti-tumor drugs, to achieve the effect of inhibiting proliferation

Active Publication Date: 2021-07-27
XIANGYA HOSPITAL CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are still few drugs available for the treatment of skin tumors, and further research is needed on other anti-skin tumor substances

Method used

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  • Anti-skin tumor compound and application thereof
  • Anti-skin tumor compound and application thereof
  • Anti-skin tumor compound and application thereof

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preparation example Construction

[0044] The preparation method comprises the following steps: react compound 1, compound 4, azidotrimethylsilane (TMSN3) and iodobenzene bistrifluoroacetate in an organic solvent to obtain the anti-skin tumor compound A. Preferably, the above-mentioned organic solvent is benzene, and the reaction preparation yield in benzene is higher.

[0045] When R in the above anti-skin tumor compound 2 When selected from -CHOH-, the reaction principle is as follows:

[0046]

[0047] The preparation method comprises the following steps: reducing the anti-tumor compound A with a reducing agent to obtain the anti-skin tumor compound B. Optionally, the reducing agent is sodium borohydride and / or lithium aluminum tetrahydride.

[0048] When R in the above anti-skin tumor compound 2 selected from -C(CH 2 )-, the reaction principle is as follows:

[0049]

[0050] The preparation method comprises the following steps: mixing and stirring methyltriphenylphosphine bromide, THF and NaOtBu...

Embodiment 1

[0063]

[0064] Compound 1 (888mg, 5mmol), compound 2 (1.16g, 20mmol) and TMSN 3 (1.15g, 10mmol) was dissolved in 30mL of benzene, and iodobenzene bistrifluoroacetate (4.3g, 10mmol) was added in portions within 5-10 minutes at room temperature. After stirring at room temperature for 24 hours, Et 3 N (12.5 mL), stirred for 10 minutes. The solvent was removed under reduced pressure and purified by column chromatography to obtain compound 3 (806 mg, 69%). 1 H NMR (500MHz, CDCl 3 )δ8.23(d, J=8.9Hz, 1H), 8.07(s, 1H), 7.52(d, J=9.0Hz, 1H), 7.46(s, 1H), 3.06(q, J=7.0Hz, 2H), 2.80(s, 3H), 1.30(t, J=7.1Hz, 3H); HRMS found: 234.0687.

[0065] Compound 3 (58 mg, 0.25 mmol) was dissolved in 3.1 mL of EtOH, and NaOH (50 mg, 1.25 mmol) was added. After stirring for 5 minutes, compound 4 (63 mg, 0.3 mmol) was added. After the reaction was complete, the mixture was extracted with EtOAc, then the combined organic layers were washed with saturated brine, washed with anhydrous Na 2 SO ...

Embodiment 2

[0068]

[0069] Dissolve 2-methyl-7-chloroquinoline (139mg, 0.785mmol), 3-formaldehyde-9-methylcarbazole (657mg, 3.14mmol), azidotrimethylsilane (181mg, 1.57mmol) in 1.5mL Add iodine bistrifluoroacetate (675mg, 1.57mmol) in batches to benzene within 10 minutes, stir at room temperature for 24 hours, add 0.5mL triethylamine and stir for 10 minutes, concentrate, and obtain A (170mg, 56% ). The NMR spectrum is: 1 H NMR (500MHz, CDCl 3 )δ8.56(s,1H),8.13(s,1H),8.05(d,J=7.8Hz,1H),8.00(d,J=8.6Hz,1H),7.75(d,J=8.9Hz, 1H), 7.55(t, J=7.6Hz, 1H), 7.48-7.41(m, 2H), 7.40-7.36(m, 2H), 7.30(t, J=7.6Hz, 1H), 3.91(s, 3H ),2.81(s,3H); 13 CNMR (125MHz, CDCl 3 )δ195.1, 159.7, 148.7, 146.1, 144.4, 141.8, 135.8, 128.3, 128.2, 127.9, 127.4, 127.0, 126.8, 124.0, 122.91, 122.87, 122.1, 120.8, 120.2, 19.5, 19.0 The resolution mass spectrum HRMS is: 385.1099, 387.1075.

[0070] Use the compound obtained in Example 2 to carry out CCK-8 test: get human skin malignant melanoma cell SK-Mel-5, make ...

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Abstract

The invention relates to an anti-skin tumor compound and application thereof. The anti-skin tumor compound has a structure represented by the following structural formula I. The anti-skin tumor compound disclosed by the invention can effectively inhibit proliferation of skin tumor cells, and especially has the minimum semi-inhibitory concentrations of 130nM and 80nM for human skin malignant melanoma cells SK-Mel-5 and SK-Mel-28 respectively, so that the anti-skin tumor compound is proved to have extremely strong capability of inducing apoptosis of the skin tumor cells, and can be applied to preparation of anti-skin tumor drugs.

Description

technical field [0001] The invention relates to the field of anti-tumor drugs, in particular to an anti-skin tumor compound and its application. Background technique [0002] Skin tumor (skin cancer) is a cell proliferative disease that occurs in the skin. It is a common disease and occurs in new organisms in the skin or subcutaneous tissue. There are many types. Clinically divided into benign tumors and malignant tumors, malignant tumors can continue to proliferate, cause metastasis, and threaten life. Generally speaking, benign tumors have a clear border, neat edges, smooth surface, and roughly symmetrical. Histological examination shows that the size and shape of tumor cell nuclei are consistent, and the arrangement is regular. Although they can grow very large, their growth is not destructive, nor A transfer occurs. On the contrary, the boundary of malignant tumors is not clear, the edges are not neat, ulcers and hemorrhages can occur on the surface, the tumor body is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D401/06A61K31/4439A61P35/00
CPCC07D401/14C07D401/06A61P35/00
Inventor 陈翔彭聪李椒端龙菁刘红平俞群军高志凌
Owner XIANGYA HOSPITAL CENT SOUTH UNIV
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