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Indolizine compound with antitumor activity and derivative of indolizine compound

A kind of technology of compound and solvate, applied in the field of indolizine compounds, can solve the problems such as indolizine derivatives that have not been reported in domestic and foreign literatures

Inactive Publication Date: 2018-11-23
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In view of the potential application of indazine anticancer drugs in cancer treatment, and the author has not seen domestic and foreign literature specifically reporting the research and development of indazine derivatives in the entire field of anticancer drugs, combined with the research work of our laboratory, this review summarizes the indazine derivatives. Azine compounds as anticancer drugs in radiosensitizers, farnesyl transferase inhibitors, cytochrome P450 inhibitors, angiogenesis inhibitors, topoisomerase inhibitors, cyclin-dependent protein kinase inhibitors and tumor resistance The latest research and development progress in drug reversal agents, etc.

Method used

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  • Indolizine compound with antitumor activity and derivative of indolizine compound
  • Indolizine compound with antitumor activity and derivative of indolizine compound
  • Indolizine compound with antitumor activity and derivative of indolizine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: Ethyl 3-(ethoxy(phenyl)methyl)indazine-1-carboxylate (yield 80%)

[0069]

[0070] Add ethyl 2-pyridinecarboxylate (0.30mmol), phenylpropynaldehyde (0.30mmol), EtOH (3.0mmol), PivOH (0.20eq.), 150mg 5A molecular sieves successively in a 25ml schlenk tube, and then pass into Ar, Reaction at room temperature for 2h. After the reaction was detected by TLC, it was extracted with ethyl carboxylate (10 mL×3), the organic layers were combined and washed with saturated brine, and then 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 to obtain a pure sample. The structure of the product 1 H NMR, 13 C NMR, GC-MS, HRMS and IR for analysis and confirmation.

[0071] 70.7 mg. 1 H NMR (400MHz, CDCl 3 )δ8.21(d, J=9.2Hz, 1H), 8.08(d, J=7.2Hz, 1H), 7.42-7.39(m, 5H), 7.09-7.05(m, 1H), 6.97(s, 1H ), 6.69-6.66...

Embodiment 2

[0073] Example 2: Ethyl 3-(methoxy(phenyl)methyl)indazine-1-carboxylate (yield 79%)

[0074]

[0075] 64.9 mg. 1 H NMR (400MHz, CDCl 3 )δ8.20(d, J=9.2Hz, 1H), 8.03(d, J=7.2Hz, 1H), 7.40-7.30(m, 5H), 7.09-7.05(m, 1H), 6.99(s, 1H ), 6.69-6.65(m, 1H), 5.58(s, 1H), 4.33(q, J=7.2Hz, 2H), 3.38(s, 3H), 1.37(t, J=7.2Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ165.0, 138.1, 137.1, 128.5, 128.0, 126.8, 125.0, 123.8, 122.6, 119.8, 117.8, 112.3, 102.9, 78.3, 59.5, 56.5, 14.6.

Embodiment 3

[0076] Example 3: Ethyl 3-(butoxy(phenyl)methyl)indazine-1-carboxylate (yield 77%)

[0077]

[0078] 74.8mg. 1 H NMR (400MHz, CDCl 3 )δ8.21(d, J=9.2Hz, 1H), 8.07(d, J=7.2Hz, 1H), 7.42-7.30(m, 5H), 7.09-7.05(m, 1H), 6.99(s, 1H ), 6.68-6.65(m, 1H), 5.68(s, 1H), 4.33(q, J=7.2Hz, 2H), 3.54-3.43(m, 2H), 1.65-1.58(m, 2H), 1.43- 1.36(m, 5H), 0.88(t, J=7.2Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ165.0, 138.7, 137.0, 128.5, 127.9, 126.8, 125.1, 124.2, 122.5, 119.8, 117.6, 112.1, 102.8, 76.7, 68.7, 59.4, 31.8, 19.4, 14.6, 13.8.

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PUM

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Abstract

The invention relates to an indolizine compound with the antitumor activity and a derivative of the indolizine compound. The indolizine compound and the derivative thereof are shown in the following description and have the inhibition effect to various cancers and tumors.

Description

technical field [0001] The present invention relates to a class of indolizine compounds, or stereoisomers thereof, or pharmaceutically acceptable salts or solvates thereof. The present invention further relates to pharmaceutical compositions containing at least the above-mentioned compounds 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 widespread 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 anticancer drugs has be...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P35/00A61K31/437
CPCA61P35/00C07D471/04
Inventor 曹华杨达基王恩明
Owner GUANGDONG PHARMA UNIV
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