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Benzo [c] benzopyrone derivative and application thereof

A technology of benzopyrone and benzopyran, which is applied in the field of benzo[c]benzopyrone derivatives and their application in the treatment of cancer diseases, and achieves the effect of obvious proliferation inhibition

Active Publication Date: 2020-08-07
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on urolithin skeleton derivatives in the field of anti-cancer has not yet been seen.

Method used

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  • Benzo [c] benzopyrone derivative and application thereof
  • Benzo [c] benzopyrone derivative and application thereof
  • Benzo [c] benzopyrone derivative and application thereof

Examples

Experimental program
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Embodiment 1

[0035] The features and advantages of the present invention can be further understood through the following detailed description in conjunction with the accompanying drawings. The examples provided are only illustrative of the method of the present invention and do not limit the rest of the present disclosure in any way. [Example 1] Preparation of 3-(3-(4-methylpiperazin-1-yl)-propyl)-6H-benzo[c]benzopyran-6-one (BH1901)

[0036] Reaction 1

[0037]

[0038] 1) Synthesis of intermediates: Weigh urolithin B (20.2g), 1,3-dibromopropane (40.4g) and potassium carbonate (27.6g) in sequence in a 500mL round bottom flask, using acetone (200mL) as solvent , 50 ° C heating reaction 2h. Thin-layer chromatography (TLC) monitors, and the reaction can be stopped after the light blue raw material fluorescent spots disappear. Spin dry the system, dissolve the solid powder with petroleum ether, and spin dry again. Using silica gel as the stationary phase, it was eluted with petroleum e...

Embodiment 2

[0042] [Example 2] Preparation of 3-(3-morpholin-1-yl)-propyl)-6H-benzo[c]benzopyran-6-one (BH1902)

[0043] Replace 4-methylpiperazine with morpholine, and prepare the target compound according to the method of Example 1. White crystals were obtained. like figure 2 shown. 1H NMR (400MHz, DMSO-d6) δ8.29(d, J=8.1Hz, 1H, Ar-H), 8.25~8.15(m, 2H, Ar-H), 7.89(t, J=7.6Hz, 1H ,Ar-H),7.58(t,J=7.5Hz,1H,Ar-H),6.97(dd,J=4.5,2.2Hz,2H,Ar-H),4.10(t,J=6.3Hz,2H , O-CH2), 3.57(t, J=4.4Hz, 4H, -CH2-O-CH2), 2.41(dd, J=18.6, 11.4Hz, 6H, N-CH2), 1.90(p, J=6.6 Hz, 2H, -CH2)., Anal. Calcd for C20H21O4N, ESI-MS: 339.38 [M+H]+.

Embodiment 3

[0044] [Example 3] Preparation of 3-(3-(4-methylpiperidin-1-yl)-propyl)-6H-benzo[c]benzopyran-6-one (BH1903)

[0045] Replace 4-methylpiperazine with 4-methylpiperidine, and prepare the target compound according to the method of Example 1. Yellow crystals were obtained. like image 3 shown. 1H NMR (400MHz, DMSO-d6) δ8.17~8.27(m, 3H, Ar-H), 7.87(t, J=7.5Hz, 1H, Ar-H), 7.56(t, J=7.5Hz, 1H ,Ar-H),6.93(d,J=6.8Hz,2H,Ar-H),4.06(t,J=5.8Hz,2H,-O-CH2-),2.81(d,J=10.9Hz,2H ), 2.39(t, J=6.9Hz, 2H, -CH2-), 1.84(t, J=9.6Hz, 4H, -CH2-), 1.54(d, J=12.0Hz, 2H, -CH2-), 1.27(s,1H,-CH-),1.11(dd,J=22.1,10.6Hz,2H,-CH2-),0.85(d,J=6.2Hz,3H,-CH3), Anal.Calcd for C22H25O3N, ESI-MS: 351.44 [M+H]+.

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Abstract

The invention discloses a benzo [c] benzopyrone derivative and application thereof. A series of chemical derivatives containing a Uro B skeleton (benzo [c] benzopyrone) as shown in a formula (I) are designed and synthesized by introducing different N-terminal end groups into a urolith derivative through a 1, 3-dibromopropane bridge chain. The invention can be applied to preparation of various anti-tumor drugs and is especially suitable for bladder cancer.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a benzo[c]benzopyrone derivative and its application in treating cancer diseases. Background technique [0002] Bladder cancer is the most common malignant tumor of the urinary system. The biological behavior of bladder tumors is complex and changeable, and they are prone to recurrence, invasion and metastasis. In addition to surgery, systemic chemotherapy has become the standard treatment for metastatic bladder cancer. Chemotherapeutic drugs commonly used in the treatment of bladder cancer include doxorubicin, hydroxycamptothecin, mitomycin, etc. However, due to the widespread emergence of drug resistance, bladder cancer cells are becoming less and less sensitive to these drugs. App doesn't work well. Therefore, the development of new anti-bladder cancer drugs is becoming more and more urgent. It is one of the hot spots in medical research to find low-toxicity an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/80C07D405/12A61K31/496A61K31/5377A61K31/453A61K31/4025A61P35/00
CPCC07D311/80C07D405/12A61P35/00
Inventor 周本宏李妍韦平兰昱
Owner WUHAN UNIV
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