2',6'-bipyridinyl substituted cannabidiol ether compound as well as preparation method and application thereof

A cannabidiol ether and compound technology, applied in the 2' field, can solve the problems of leukopenia, thrombocytopenia, etc., achieve good biological activity, obvious effect, and obvious effect of inhibiting tumor cell proliferation

Active Publication Date: 2021-07-09
FUJIAN SANAN SINO SCI PHOTOBIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a large number of clinical medicine shows that gemcitabine also has some side effects: mainly manifested as myelosuppression, thrombocytopenia, leukopenia, etc., and even some patients' digestive system will also produce side effects, such as diarrhea, stomatitis, etc., causing fever, fever, and headache , loss of appetite, etc.

Method used

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  • 2',6'-bipyridinyl substituted cannabidiol ether compound as well as preparation method and application thereof
  • 2',6'-bipyridinyl substituted cannabidiol ether compound as well as preparation method and application thereof
  • 2',6'-bipyridinyl substituted cannabidiol ether compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] Compound I-1 synthesis steps are as follows:

[0057] Take a 10mL reaction bottle, add CBD (100mg, 0.32mmol), chloride (108.6mg, 0.64mmol), solvent DMF (1mL) in sequence, mix well and remove oxygen, add Cs 2 CO 3 (207.2 mg, 0.64 mmol), placed in an oil bath at 100°C, reacted for 24 hours, TLC detected the completion of the reaction, cooled to room temperature, placed in an ice-water bath, added 1N HCl to the system to adjust the pH to 3-5, and extracted with ether , combined organic phases, washed once with saturated sodium bicarbonate, washed once with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography (200-300 mesh silica gel; n-hexane:ethyl acetate=2:1) ​​to obtain The crude product was used (300-400 mesh silica gel; n-hexane: acetone = 2:1) to obtain the target compound (15 mg, yield 6.7%). 1 H NMR (400MHz, CDCl 3 )δ7.78(s,4H),6.77(s,2H),4.89(s,1H),4.46(s,2H),4.02(s,12H),3....

Embodiment 2

[0060]

[0061] Referring to Example 1 for the synthetic steps of compound I-2, the target compound I-2 (16 mg, yield 5%) was obtained. 1 H NMR (400MHz, CDCl 3 )δ8.60(d,J=5.6Hz,2H),7.63(s,2H),6.92(d,J=3.3Hz,2H),6.72(s,2H),5.37–5.28(m,2H), 4.90(s,1H),4.50(s,1H),4.47(s,1H),3.67(d,J=8.9Hz,1H),2.81–2.69(m,1H),2.55(t,J=7.6Hz ,2H),2.00–1.77(m,2H),1.73–1.47(m,4H),1.57(s,3H),1.42(d,J=6.2Hz,12H),1.34–1.21(m,4H), 1.13(s,3H),0.86(t,J=6.8Hz,3H).MS(ESI)m / z:641[M+H] + .

Embodiment 3

[0063]

[0064] Referring to Example 1 for the synthetic steps of compound I-3, the target compound I-3 (11.4 mg, 5.3%) was obtained. 1 H NMR (400MHz, CDCl 3 )δ8.59(d, J=5.6Hz, 2H), 7.63(s, 2H), 6.93(d, J=3.3 Hz, 2H), 6.73(s, 2H), 4.89(s, 1H), 4.49( s,1H),4.47(s,1H),4.41(t,J=6.9Hz, 4H),3.68(d,J=10.4Hz,1H),2.82–2.71(m,1H),2.55(t,J =7.6Hz,2H),1.98–1.74(m,6H),1.71–1.59(m,2H),1.57–1.51(m,2H),1.50-1.43(m,4H),1.42(s,3H), 1.34–1.26(m,4H),1.12(s,3H),0.97(t,J=7.4Hz,6H),0.87(t,J=6.8Hz, 3H).MS(ESI)m / z:669[ M+H] + .

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Abstract

The invention discloses a 2',6'-bispyridinyl substituted cannabidiol ether compound as shown in a formula I and a preparation method and application thereof. The 2',6'-bispyridinyl substituted cannabidiol ether compound is a novel compound and is obtained through synthesis, and cell experiments find that the compound has good anti-tumor cell proliferation activity and especially has an obvious tumor cell proliferation inhibition effect in lung cancer cells. The compound obtained by the method is high in purity, good in stability and good in biological activity. When the compound is combined with gemcitabine for use, the effect of inhibiting tumor cell proliferation is more obvious.

Description

technical field [0001] The present invention relates to a class of pharmaceutical compounds, in particular to a 2', 6'-bispyridine substituted cannabidiol ether compound and its preparation method and application. Background technique [0002] Different living habits and environmental factors have led to a gradual increase in the incidence of cancer, becoming one of the most serious diseases in humans. Single-drug chemotherapy, as a commonly used clinical tumor treatment method, can no longer achieve the purpose of killing tumor cells. In order to achieve the therapeutic effect, drug combination has become the most commonly used method in chemotherapy, and combined drug therapy can also produce an optimal combination dose to minimize side effects. [0003] Gemcitabine (Gemcitabine) is a pyrimidine nucleoside analogue, its main metabolite is incorporated into DNA in cells, and mainly acts on G1 / S phase. It is often used as a first-line application for locally advanced (stag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/79C07D213/803A61P35/00
CPCC07D213/79C07D213/803A61P35/00
Inventor 张靖林祖铭张婷
Owner FUJIAN SANAN SINO SCI PHOTOBIOTECH CO LTD
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