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Benzylguanine derivatives and their organic salt compounds and pharmaceutical compositions and their applications

A technology of benzylguanine and derivatives, applied in the field of benzylguanine derivatives and their organic salt compounds and pharmaceutical compositions, can solve the problems of poor cell membrane permeability and low Pin1 affinity, and achieve easy preparation and druggability Good, promote biosynthesis effect

Active Publication Date: 2020-05-05
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to problems such as poor cell membrane permeability and low Pin1 affinity, no specific Pin1 inhibitors have been reported in clinical research so far.

Method used

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  • Benzylguanine derivatives and their organic salt compounds and pharmaceutical compositions and their applications
  • Benzylguanine derivatives and their organic salt compounds and pharmaceutical compositions and their applications
  • Benzylguanine derivatives and their organic salt compounds and pharmaceutical compositions and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] A benzylguanine derivative (compound 1) provided in this example has a structural formula as shown below.

[0063]

[0064] The structure of the benzylguanine derivative prepared by the embodiment of the present invention is passed 1 H NMR, 13 C NMR and HR-ESIMS for analytical determination. Specific map see figure 1 , figure 2 and image 3 . white solid. 1 H NMR (400MHz, Methanol-d 4 )δ7.86(s,1H), 7.52(d,J=7.2Hz,3H),7.42-7.29(m,4H),5.56(s,2H). 13 C NMR (100 MHz, Methanol-d 4 )δ160.32, 160.05, 153.83, 138.65, 136.54, 128.07, 128.01, 127.74, 118.32, 67.58.HR-ESIMS: 242.1041[M+H] + (calc.for C 12 h 12 N 5 O, 242.1037).

Embodiment 2

[0066] A benzylguanine derivative (compound 2) provided in this example has a structural formula as shown below.

[0067]

[0068] The structure of the benzylguanine derivative prepared by the embodiment of the present invention is passed 1 H NMR, 13 C NMR and HR-ESIMS for analytical determination. Specific map see Figure 4 , Figure 5 and Figure 6 . white solid. 1 H NMR (400MHz, DMSO-d 6 )δ12.49(s,1H), 7.86(s,1H),7.74-7.61(m,1H),7.59-7.51(m,1H),7.49-7.35(m,2H),6.34(s,2H) ,5.57(s,2H). 13 C NMR (100MHz, DMSO-d 6 )δ 162.22, 160.11, 156.54, 138.40, 134.67, 133.19, 130.88, 130.42, 129.82, 127.85, 114.46, 64.63. HR-ESIMS: 267.0650[M+H] + (calc.for C 12 h 11 ClN 5 O, 267.0647).

Embodiment 3

[0070] A benzylguanine derivative (compound 3) provided in this example has a structural formula as shown below.

[0071]

[0072] The structure of the benzylguanine derivative prepared by the embodiment of the present invention is passed 1 H NMR, 13 C NMR and HR-ESIMS for analytical determination. Specific map see Figure 7 , Figure 8 and Figure 9 . white solid. 1 H NMR (400MHz, DMSO-d 6 )δ12.53(s,1H), 7.87(s,1H),7.46(d,J=8.1Hz,2H),7.28(d,J=8.1Hz,2H),6.34(s,2H),5.45( s,2H),2.47(s,3H). 13 C NMR (100MHz, DMSO-d 6 )δ 161.43, 160.10, 156.54, 138.83, 138.53, 133.70, 129.78, 126.25, 120.05, 66.85, 15.13. HR-ESIMS: 268.0909[M+H] + (calc.for C 13 h 14 N 5 OS, 268.0913).

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Abstract

The invention relates to the field of antitumor drugs, and in particular to a benzylguanine derivative and its organic salt compound, a pharmaceutical composition and applications thereof. The benzylguanine derivative is easy to prepare and has good druggability, can inhibit the enzymatic activity of Pin1 protein, can promote the biosynthesis of mature microRNA at the level of cells and animals, and increases the types of antitumor drugs.

Description

technical field [0001] The invention relates to the field of antitumor drugs, and in particular to a benzylguanine derivative and its organic salt compound, a pharmaceutical composition and applications thereof. Background technique [0002] Studies have shown that microRNA (miRNA) is abnormally transcribed in liver cancer tissue, which is closely related to the occurrence and development of liver cancer. The transport protein exportin-5 (XPO5) is a nuclear transport protein that shuttles between the nucleus and the cytoplasm, plays an important role in the biosynthesis of miRNA, and is closely related to the level of mature miRNA. Studies have shown that XPO5 is phosphorylated by the serine / threonine protein kinase ERK in liver cancer. Phosphorylated XPO5 is regulated by peptide prolyl cis-trans isomerase Pin1 (peptidyl-prolylcis / trans isomerase, NIMA-interacting 1) and changes its configuration, stays in the nucleus, and cannot effectively transport pre-miRNA to the cytop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/18A61K31/52A61P35/00
CPCC07D473/18
Inventor 彭勇魏于全蒲文臣李姣
Owner SICHUAN UNIV
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