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Imidazate compounds with anticancer activity and derivatives of imidazate compounds

A compound and solvate technology, applied in the field of cancer treatment, can solve problems such as imidazole derivatives that have not been specifically reported in domestic and foreign literature

Active Publication Date: 2017-11-07
无锡恩桥医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the potential application of imidazole anticancer drugs in cancer treatment, and the author has not seen domestic and foreign literatures that specifically report on the research and development of imidazole derivatives in the entire field of anticancer drugs, combined with the research work of our laboratory, this review summarizes imidazole compounds. As an anticancer drug in radiosensitizers, farnesyl transferase inhibitors, cytochrome P450 inhibitors, angiogenesis inhibitors, topoisomerase inhibitors, cyclin-dependent protein kinase inhibitors and tumor resistance reversal agents The latest research and development progress in the field of

Method used

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  • Imidazate compounds with anticancer activity and derivatives of imidazate compounds
  • Imidazate compounds with anticancer activity and derivatives of imidazate compounds
  • Imidazate compounds with anticancer activity and derivatives of imidazate compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: (1,2-diphenyl-1H-imidazol-5-yl)(phenyl)methylpropionate (yield 72%)

[0073]

[0074] Add N-phenylbenzamidine (0.20mmol), phenylpropynaldehyde (0.20mmol), acetic acid (0.60mmol), AgOAc (2.0mol%), 3.0ml CH 2 Cl 2 , then pass into N 2 , Reaction at 60°C for 10h. After the completion of the reaction was detected by TLC, cooled to room temperature, 10 mL of saturated brine was added to the reaction mixture, and then extracted with ethyl acetate (10 mL×3), the combined organic layers were washed with saturated brine, and washed with anhydrous MgSO 4 to dry. The obtained organic phase was distilled off under reduced pressure to remove most of the solvent, and the crude product was separated and purified by column chromatography. The structure of the product 1 H NMR, 13 C NMR, GC-MS, HRMS and IR for analysis and confirmation.

[0075] Yellow oily liquid.55.0mg. 1 H NMR (400MHz, CDCl 3 )δ7.41 (d, J=7.2Hz, 2H), 7.35-7.29 (m, 8H), 7.21-7.19 (m, 5H), 6.94 (s...

Embodiment 2

[0077] Example 2: (1,2-diphenyl-1H-imidazol-5-yl)(phenyl)methylbutyrate (yield 78%)

[0078]

[0079] Yellow oily liquid. 61.8mg. 1 H NMR (400MHz, CDCl 3 )δ7.41 (d, J=7.2Hz, 3H), 7.34-7.19 (m, 12H), 6.95 (s, 1H), 6.67 (s, 1H), 2.17-2.10 (m, 2H), 1.56-1.47 (m, 2H), 0.86(t, J=7.6Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ171.9, 148.5, 137.5, 136.6, 133.3, 129.8, 129.5, 129.2, 129.1, 128.5, 128.4, 128.4, 128.4, 128.1, 127.1, 68.8, 35.9, 18.1, 13.6. ESI-MS m / z (%) 396(100)[M+H] + ;Anal.Calcd for C 26 h24 N 2 o 2 C, 78.76; H, 6.10; N, 7.07; Found: C, 78.85; H, 6.07; N, 7.04.

Embodiment 3

[0080] Example 3: (1,2-diphenyl-1H-imidazol-5-yl)(phenyl)methylvalerate (yield 76%)

[0081]

[0082] Yellow oily liquid. 62.5mg. 1 H NMR (400MHz, CDCl 3 )δ7.41 (d, J=7.2Hz, 3H), 7.34-7.19 (m, 12H), 6.94 (s, 1H), 6.67 (s, 1H), 2.19-2.12 (m, 2H), 1.51-1.43 (m, 2H), 1.26-1.21 (m, 2H), 0.89 (t, J=7.2Hz, 3H.) 13 C NMR (100MHz, CDCl 3 ( 100)[M+H] + ;Anal.Calcd for C 27 h 26 N 2 o 2 C, 79.00; H, 6.38; N, 6.82; Found: C, 78.93; H, 6.41; N, 6.85.

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PUM

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Abstract

The invention relates to imidazate compounds with anticancer activity and derivatives of the imidazate compounds. The compounds and the derivatives of the compounds have inhibition effects on various tumors and cancers, and the compounds are shown in the general formula shown in the specification.

Description

technical field [0001] The present invention relates to a class of imidazole ester compounds, or stereoisomers thereof, or pharmaceutically acceptable salts or solvates thereof. The present invention further relates to pharmaceutical compositions containing at least one compound according to the invention for use in the treatment of cancer. Background technique [0002] Cancer is one of the important diseases that seriously threaten human health, and its treatment and prevention have attracted extensive attention. The current treatment methods include surgical resection, radiotherapy, chemical drug therapy, etc., but still mainly rely on chemical drug therapy. Currently, there are many kinds of chemical drugs used clinically to treat cancer, such as platinum, nitrogen mustards, triazoles, etc., but the application of most drugs is limited due to high toxicity, many adverse reactions, and low bioavailability. Therefore, searching for highly effective and low-toxic anticance...

Claims

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Application Information

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IPC IPC(8): C07D233/64A61K31/4174A61P35/00A61P35/02
CPCC07D233/64
Inventor 曹华
Owner 无锡恩桥医药科技有限公司