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Dioxobenzothiazole compound as well as preparation method and use thereof

A technology of benzothiazole quinone and compound is applied in the field of new drug use to achieve the effects of convenient administration, enhanced anti-tumor activity and good anti-tumor activity

Inactive Publication Date: 2019-03-19
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, dual-target drug design targeting NAMPT and NQO1 has not been reported so far

Method used

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  • Dioxobenzothiazole compound as well as preparation method and use thereof
  • Dioxobenzothiazole compound as well as preparation method and use thereof
  • Dioxobenzothiazole compound as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of compound P2:

[0033] According to the general law, the amine compounds are The product was obtained as a purple solid with a yield of 28%.

[0034] ESI-MS, m / z, [M+H + ] calcd 451.2, found 451.2; 1 H NMR (300MHz, DMSO-d6) δ (ppm): 8.96(s, 1H), 8.73(s, 1H), 8.53(d, J=4.5Hz, 1H), 8.12(s, 2H), 7.95(d ,J=7.7Hz,1H),7.45~7.40(m,2H),6.71(d,J=15.9Hz,1H),5.88(s,1H),4.08(d,J=12.6Hz,2H),3.18 ~3.02(m,4H),1.76(d,J=12.0Hz,2H),1.57~1.43(m,4H),1.32~1.22(m,6H).

Embodiment 2

[0036] Preparation of compound P3:

[0037] According to the general law, the amine compounds are The product was obtained as an orange-red solid with a yield of 31%.

[0038] ESI-MS, m / z, [M+H + ] calcd 369.1, found 369.1; 1 H NMR(300MHz,DMSO-d6)δ(ppm):9.02(s,1H),8.75(s,1H),8.54(d,J=3.8Hz,1H),8.23(m,1H),8.02~7.96 (m,2H),7.48~7.41(m,2H),6.71(d,J=15.9Hz,1H),5.62(s,1H),3.33~3.24(m,4H),1.81~1.76(m,2H ).

Embodiment 3

[0040] Preparation of compound P4:

[0041] According to the general law, the amine compounds are The product was obtained as a purple solid with a yield of 29%.

[0042] ESI-MS, m / z, [M+H + ] calcd 382.1, found 382.2; 1 H NMR(300MHz,DMSO-d6)δ(ppm):9.01(s,1H),8.72(s,1H),8.52(d,J=4.0Hz,1H),8.15(m,1H),8.03(s ,1H),7.93(d,J=7.7Hz,1H),7.44~7.39(m,2H),6.69(d,J=15.9Hz,1H),5.60(s,1H),3.29~3.19(m, 4H),1.60~1.50(m,4H).

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Abstract

The invention discloses a dioxobenzothiazole compound represented by a general formula I (shown in the description) or a pharmaceutically acceptable salt, a preparation method of the benzothiazole quinone compound and application of the benzothiazole quinone compound in the preparation of anti-tumor drugs. The structure of the compound is represented by a formula (shown in the description), wherein n represents 2-8, and X is selected from -CH2-, -NH-, -O- or formula; and R is selected from formula shown in the description. Compared with the prior art, a mother nucleus structure of a natural product pronqodine A is spliced with a key pharmacophore of an NAMPT inhibitor by virtue of a splicing principle so as to form a molecule. The compounds have very good anti-tumor activities in moleculeand cell levels, are capable of generating a large number amount of active oxygen substances in high-expression NQO1 tumor cells and effectively inhibiting the activity of nicotinamide phosphoribosyltransferase (NAMPT) and can be used for preparing anti-tumor drugs.

Description

technical field [0001] The invention belongs to the technical field of new application of medicines, and in particular relates to a benzothiazole quinone compound and its preparation method and application. Background technique [0002] The development of small molecule anticancer drugs targeting tumor metabolism has gradually become a hot research field. Important breakthroughs have been made in the development of new drugs targeting tumor-specific highly expressed metabolic enzymes, including the development of NAMPT inhibitors. Although NAMPT inhibitors represented by FK866 have entered the stage of clinical research, due to poor bioavailability and other reasons, the clinical trials ended in failure. [0003] Previous studies have found that the combination of NQO1 substrates and NAMPT inhibitors can selectively kill tumor cells. The specific mechanism is that NQO1 substrates undergo a reduction-autooxidation process to generate a large amount of reactive oxygen species...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D417/14A61P35/00A61K31/4545A61K31/4439
CPCA61P35/00C07D417/12C07D417/14
Inventor 郝海平徐小为赵洲
Owner CHINA PHARM UNIV
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