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4-aminoquinazolinehydroxamic acid compounds and applications thereof as antitumor medicaments

A technology of aminoquinazoline hydroxime and compound, which is applied in the application field of antineoplastic drugs, can solve problems such as limited therapeutic range, cell death, and adverse reactions, and achieve good selective inhibitory activity, weak inhibitory effect, and good inhibitory activity Effect

Active Publication Date: 2013-12-04
SINOPHARM A THINK PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional chemotherapeutic drugs non-specifically block cell division and cause cell death. While killing tumor cells, they also destroy normal human cells
Moreover, many cytotoxic drugs have limited therapeutic range and are likely to cause treatment-related adverse reactions

Method used

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  • 4-aminoquinazolinehydroxamic acid compounds and applications thereof as antitumor medicaments
  • 4-aminoquinazolinehydroxamic acid compounds and applications thereof as antitumor medicaments
  • 4-aminoquinazolinehydroxamic acid compounds and applications thereof as antitumor medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Ⅴ-1 Synthesis of N-hydroxy-7-(quinazoline-4-amino)heptanamide

[0077] 4-Chloroquinazoline (0.164g, 1mmol), 7-aminoheptanoic acid methyl ester hydrochloride (0.21g, 1mmol), KOH (0.14g, 2.5mmol), hydroxylamine hydrochloride (0.7g, 2.5mmol) as raw materials, Ⅴ-1 was synthesized according to the general synthesis method of class V compounds, and the yield was 55.9%.

[0078] ESI-MS[M+H] + :m / z 289.1695

[0079] 1 H NMR (400MHz, DMSO-d 6 )δppm: 1.30(m, 4H), 1.48(m, 2H), 1.60(m, 2H), 1.70-1.80(m, 3H), 1.95(t, 1H, J=8.0Hz), 3.52(m, 2H ),7.49(t,1H,J=8.0Hz),7.66(d,1H,J=8.0Hz),7.75(t,1H,J=8.0Hz),8.27(d,1H,J=8.0Hz), 8.34(s,1H),8.43(s,1H)

Embodiment 2

[0081] Ⅴ-2 Synthesis of N-hydroxy-7-(6,7-dimethoxyethoxyquinazoline-4-amino)heptanamide

[0082] 6,7-dimethoxyethoxy-4-chloroquinazoline (0.312g, 1mmol), methyl 7-aminoheptanoate hydrochloride (0.21g, 1mmol), KOH (0.14g, 2.5mmol), Hydroxylamine hydrochloride (0.7g, 2.5mmol) was used as a raw material, and V-2 was synthesized according to the general synthesis method of class V compounds, with a yield of 65.3%.

[0083] ESI-MS[M+H] + :m / z 437.2449

[0084] 1 H NMR (400MHz, DMSO-d 6 )δppm: 1.32(m, 4H), 1.42-1.63(m, 4H), 1.96(t, 2H, J=8.0Hz), 2.21(t, 1H, J=8.0Hz), 3.34-3.51(m, 7H ),3.73(s,6H),4.25(m,4H),7.15(s,1H),7.91(s,1H),8.38(s,1H),8.64(s,1H)

Embodiment 3

[0086] Ⅴ-3 Synthesis of N-hydroxy-7-(6,7-dimethoxyquinazoline-4-amino)heptanamide

[0087]6,7-dimethoxy-4-chloroquinazoline (0.224g, 1mmol), methyl 7-aminoheptanoate hydrochloride (0.21g, 1mmol), KOH (0.14g, 2.5mmol), hydroxylamine hydrochloride ( 0.7g, 2.5mmol) as raw materials, and synthesized V-3 according to the general synthesis method of class V compounds, with a yield of 66.0%.

[0088] ESI-MS[M+H] + :m / z 349.32

[0089] 1 H NMR (400MHz, DMSO-d 6 )δppm: 1.32(m, 4H), 1.49(m, 2H), 1.61(m, 2H), 1.69(s, 1H), 1.96(t, 2H, J=8.0Hz), 3.48-3.57(m, 3H ),3.88(s,6H),7.06(s,1H),7.66(s,1H),8.06(s,1H),8.32(s,1H)

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Abstract

The invention discloses 4-aminoquinazolinehydroxamic acid compounds and applications thereof as antitumor medicaments. The compounds have good histone deacetylase inhibiting activity, have good inhibiting effects on multiple tumor cells of a human body, have weak inhibiting effects on normal cells and small toxicity, and are suitable for being developed as antitumor medicaments. The compounds also have good treatment effects on diseases caused by abnormal genetic expression. The 4-aminoquinazolinehydroxamic acid compounds are compounds or pharmaceutically acceptable salts shown as formula V.

Description

technical field [0001] The invention relates to a class of 4-aminoquinazoline hydroxamic acid compounds and the application of the compounds as antitumor drugs. Background technique [0002] Tumor is a major disease that threatens human health, and the treatment of tumor has been paid close attention to all over the world. Traditional chemotherapy drugs non-specifically block cell division and cause cell death. While killing tumor cells, they also destroy normal cells in the human body. Moreover, many cytotoxic drugs have a limited therapeutic range and are prone to cause treatment-related adverse reactions. [0003] In recent years, with the continuous improvement of molecular biology technology and the further understanding of tumor pathogenesis at the cellular and molecular levels, as well as the rapid development of technologies such as combinatorial chemistry, structure-based drug design and computer science, tumor biotherapy has become a reality. Great progress has e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/94A61K31/517A61P35/00
CPCA61K31/517C07D239/94A61P35/00
Inventor 李建其张庆伟贾志丹周斌崔宁梁晓东
Owner SINOPHARM A THINK PHARMA
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