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Camphoryl thiosemicarbazones, and preparation method and anti-tumor activity thereof

A technology of thiosemicarbazones and compounds, which is applied in antineoplastic drugs, organic chemistry, drug combinations, etc., can solve the problems of high toxicity in clinical application and chemotherapy side effects, and achieve the effect of abundant sources and simple preparation process

Inactive Publication Date: 2019-12-10
NANJING FORESTRY UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemotherapy is the most commonly used method to treat cancer, but chemotherapy has a lot of side effects, and many auxiliary anticancer drugs are also limited in clinical application due to toxicity, so it is still necessary to develop some low-toxicity and high-efficiency anticancer drugs

Method used

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  • Camphoryl thiosemicarbazones, and preparation method and anti-tumor activity thereof
  • Camphoryl thiosemicarbazones, and preparation method and anti-tumor activity thereof
  • Camphoryl thiosemicarbazones, and preparation method and anti-tumor activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 2-(3-(2′-fluorobenzylidene)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)hydrazinethiocarboxamide (compound 1):

[0029]

[0030] In a 50ml three-neck flask equipped with a magnetic stirrer, a thermometer and a reflux condenser, add thiosemicarbazide (2mmol) and ethanol (35mL) in sequence, start stirring to dissolve the thiosemicarbazide, add 3-(2'-fluoro After benzylidene)camphor (2mmol), the temperature was raised to 90°C, 3 drops of concentrated hydrochloric acid were added dropwise, and the reflux reaction was continued for 48 hours (TLC tracking detection). After the reaction, the reaction solution was concentrated to remove ethanol to obtain a yellow crude product. The crude product was purified by column chromatography (ethyl acetate: petroleum ether = 1:6, 1% TEA) to obtain a light yellow solid powder. Yield 78.9%; m.p.156.1~156.5℃; 1 H NMR (400MHz, CDCl 3 ): δ9.22(s, 1H), 7.36(s, 1H), 7.25-7.32(m, 2H), 7.23(s, 1H), 7.07-7.18(m, 2H), 6.40(s, 1...

Embodiment 2

[0032] Preparation of 2-(3-(4′-fluorobenzylidene)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)hydrazinethiocarboxamide (Compound 2):

[0033]

[0034] The preparation method is the same as in Example 1. Substitute 2-fluorobenzaldehyde with 4-fluorobenzaldehyde to obtain light yellow solid powder. Yield 79.4%; m.p.192.5~192.9℃; 1 H NMR (400MHz, CDCl 3 ): δ9.18(s, 1H), 7.30(t, J=4Hz, 2H), 7.27(s, 1H), 7.21(s, 1H), 7.07(t, J=8Hz, 2H), 6.40(s , 1H), 2.86(d, J=4Hz, 1H), 2.05-2.10(m, 1H), 1.77-1.87(m, 1H), 1.53(d, J=12Hz, 1H), 1.04(s, 3H) , 0.91(s, 3H), 0.75(s, 3H); 13 C NMR (100MHz, CDCl 3 ): δ179.92, 161.20, 158.90, 141.22, 132.18, 130.86, 128.72, 115.72, 54.17, 51.71, 47.97, 33.42, 25.77, 20.01, 18.19, 11.28; HR-MS (ESI): m / z calculated for C 18 h 22 FN 3 S, [M+H] + 332.1597, found 332.1591.

Embodiment 3

[0036] Preparation of 2-(3-(2′-chlorobenzylidene)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)hydrazinethiocarboxamide (compound 3):

[0037]

[0038] The preparation method is the same as in Example 1. Substitute 2-chlorobenzaldehyde for 2-fluorobenzaldehyde to obtain light yellow solid powder. Yield 82.6%; m.p.199.7~200.5℃; 1 H NMR (400MHz, CDCl 3 ): δ9.24(s, 1H), 7.41-7.43(m, 1H), 7.39(s, 1H), 7.32(s, 1H), 7.26(t, J=4Hz, 2H), 7.21-7.24(m , 1H), 6.46(s, 1H), 2.66(d, J=4Hz, 1H), 1.97-2.03(m, 1H), 1.81-1.86(m, 1H), 1.51(d, J=8Hz, 2H) , 1.05(s, 1H), 0.89(s, 1H), 0.80(s, 1H);13 C NMR (100MHz, CDCl 3 ): δ 179.96, 158.11, 142.78, 134.71, 133.85, 130.24, 129.62, 129.33, 126.77, 117.60, 54.37, 51.67, 47.75, 33.36, 25.90, 20.07, 18.12, 11.26 for C 18 h 22 ClN 3 S; [M+H] + 348.1301, found 348.1297.

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Abstract

The invention discloses camphoryl thiosemicarbazones, and a preparation method and an anti-tumor activity study thereof. With camphor as a raw material and under an alkaline catalysis condition, a series of alpha,beta-unsaturated ketones are obtained through aldol condensation reaction of camphor with different aromatic aldehydes respectively, then a series of camphoryl thiosemicarbazones are obtained through condensation of alpha,beta-unsaturated ketones with thiosemicarbazide through catalysis of concentrated hydrochloric acid, and the anti-tumor activity of all the target products is studied. Experiments show that the camphoryl thiosemicarbazones have good inhibitory activity on human multiple myeloma cells (RPMI-8226), human breast cancer cells (MDA-MB-231) and human non-small cell lung cancer cells (A549), have less toxicity on normal cell human gastric mucosa cells (GES-1), thereby having potential anti-tumor application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and drug synthesis, and relates to the preparation and antitumor activity of camphoryl thiosemicarbazone compounds. Background technique [0002] Tumor is the most serious disease that endangers human health. Because tumor cells are easy to migrate, reproduce quickly, and easily mutate, the morbidity and mortality of cancer have remained high. Chemotherapy is the most commonly used method to treat cancer, but chemotherapy has a lot of side effects, and many adjuvant anticancer drugs are also limited in clinical application due to toxicity, so it is still necessary to develop some low-toxicity and high-efficiency anticancer drugs. Due to the diversity of natural product structures and a wide range of physiological activities, obtaining anticancer drugs from natural products has become a hot field for the development of anticancer drugs at home and abroad. Camphor is a high-yield natural ...

Claims

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Application Information

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IPC IPC(8): C07C337/08C07D213/53A61P35/00
CPCC07C337/08C07D213/53C07C2602/42
Inventor 王石发张燕徐徐王忠龙谷文杨益琴徐海军匡红波周新成
Owner NANJING FORESTRY UNIV
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