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Indolylpyrimidine ring-containing hydrazone compound, and preparation method and application thereof

A technology of indole pyrimidine ring hydrazones and compounds, which is applied in the field of a class of indole pyrimidine ring hydrazone compounds and their preparation and application, can solve the problems that no one has synthesized hydrazone compounds, achieve good tumor performance, and improve self Antitumor activity, effect of enhancing antitumor activity

Inactive Publication Date: 2018-02-16
临猗县安盖特生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, no one has synthesized hydrazone compounds containing indole pyrimidine rings.

Method used

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  • Indolylpyrimidine ring-containing hydrazone compound, and preparation method and application thereof
  • Indolylpyrimidine ring-containing hydrazone compound, and preparation method and application thereof
  • Indolylpyrimidine ring-containing hydrazone compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] a) Synthesis of 2-(2-benzylhydrazino)-4-(1H-indole-3-carbonyl)-pyrimidine-5-carbonitrile.

[0047]

[0048] Step 1: Synthesis of 3-(1H-indole-3-)-3-oxopropanecyanide

[0049] Weigh 11.72 g of indole and 8.51 g of cyanoacetic acid, put them into a 500 mL pear-shaped bottle, add 100 mL of acetic anhydride, adjust to 40°C, react for 4 hours, cool and filter, wash with methanol, and dry to obtain 15.66 g of white powder. The rate is 85%, and the melting point is 240~241°C.

[0050] The second step: Synthesis of 3-dimethylamino-2-(1H-indole-3-carbonyl)-acrylonitrile

[0051] Add 20 mL of toluene dissolved with 6.0g of DMF-DMA into 150 mL of toluene dissolved with 9.2g of 3-(1H-indole-3-)-3-oxopropanecyanide, heat to 120°C, react for 3h, and cool After suction filtration, a yellow solid was obtained, which was recrystallized from ethanol to obtain 10.82 g of a yellow powder, with a yield of 90.2% and a melting point of 160-161°C.

[0052] Step 3: Synthesis of N-(5-cyano...

Embodiment 2

[0060] b) Preparation of 2-(2-(4-methylbenzyl)hydrazino)-4-(1H-indole-3-carbonyl)-pyrimidine-5-carbonitrile.

[0061] Prepared according to the method and conditions of Example 1. The first, second, third, and fourth steps are the same as in Example one, except that the fifth step adds 0.50 g of 2-hydroxybenzaldehyde, and the target product yield is 41.7%.

[0062]

[0063] Molecular formula: C 21 h 14 N 6 ; Yield: 85.7%; Off-white powdery solid; m.p.>250℃; ESI-MS: 353.2,[M+H] +,375.1 [M+Na] +; IR (KBr, cm-1) v: 3283, 3207, 2978, 2220,1570, 1528,1506, 1487, 1447, 1416, 1259, 1144, 1096, 810, 795, 754; 1H NMR(500 MHz,DMSO) δ (ppm) (TMS as internal standard): 12.11 (s, 1H, indole-NH), 11.88 (s, 1H, NH), 9.33(s, 1H, Pyr-H), 8.78 (s, 1H), 8.63 (s, 1H, Ph-H), 8.30 ( 13C NMR(125 MHz, DMSO) δ (ppm): 163.6, 163.5, 159.9, 144.8, 140.0, 137.0, 131.1, 130.0, 127.2, 123.6, 121.9, 119.9, 112.8, 91.3, 21.6.

Embodiment 3

[0065] c) Preparation of 2-(2-(4-fluorobenzyl)hydrazino)-4-(1H-indole-3-carbonyl)-pyrimidine-5-carbonitrile.

[0066] Prepared according to the method and conditions of Example 1. The first, second, third, and fourth steps are the same as in Example 1, except that 0.50 g of 2-fluorobenzaldehyde is added in the fifth step, and the yield of the target product is 75.8%.

[0067]

[0068] Molecular formula: C 20 h 13 FN 6 ; Yield: 72.5%; Earthy yellow powdery solid; m.p.>250℃; ESI-MS: 357.1[M+H] +, 379.1 [M+Na] +; IR (KBr, cm-1) v: 3308, 1H NMR (500 MHz, DMSO) (pp TMS as internal standard): 12.12 (s,1H, indole-NH), 9.31(s, 1H, Pyr-H), 8.80 (s, 1H), 8.6 (s, 1H, NCH), 8.32 (s, 1H, Ph-H), 7.91 (s,2H, Ph-H), 7.60 (d, 1H, J=8.6Hz, Ph-H), 7.42 (s, 3H, Ph-H), 7.31(d, 1H, J =8.0Hz, Ph-H); 13 C NMR (125 MHz, DMSO) δ (ppm): 164.4, 163.6,162.4, 159.8,143.7, 136.9, 131.1, 129.1, 124.7, 123.7, 122.0, 119.8, 116.57,1 , 112.8, 91.3.

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Abstract

The invention discloses a class of hydrazone compounds containing indole pyrimidine ring. Indole, cyanoacetic acid and DMF-DMA are used as raw materials to synthesize the intermediate 3-(dimethylamino)-2-(1H-indole-3-carbonyl)-acrylonitrile through a two-step reaction, and then synthesized with nitroguanidine Ring, nitro reduction to obtain the key intermediate 2-hydrazino-4-(1H-indole-3-carbonyl)-pyrimidine-5-carbonitrile, and then react with different aromatic aldehydes to obtain the target product; these compounds also contain Two types of active structures of indole pyrimidine ring and acylhydrazone, so it has stronger potential biological activity. In vitro anti-tumor tests show that the compound has a strong inhibitory effect on test tumor cells, and can be further developed as an anti-tumor drug or lead compound .

Description

technical field [0001] The invention relates to a new class of hydrazone compounds containing indole pyrimidine rings and a preparation method thereof. The compounds have excellent activity against human tumor cells. Background technique [0002] Cancer refers to a local mass formed by the abnormal proliferation of cells in local tissues under the action of various tumorigenic factors. Uncontrolled cell growth and cell cycle disorders are common characteristics of all cancers. The ability of normal human cells to replicate depends on the activation and inhibition of cyclin-dependent kinases by cyclins. Studies have shown that the overexpression of cyclins, mutations and abnormal functions of cyclin-dependent kinase inhibitors can be seen in a variety of tumor diseases, so they cannot stop the process of cells in the cycle, resulting in the infinite growth of cancer cells. Therefore, people try to use various regulators of the cell cycle as molecular targets to regulate and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04A61K31/506A61P35/00
CPCC07D403/04
Inventor 王磊薛岩王岩王京
Owner 临猗县安盖特生物科技有限公司
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