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N-heterocyclic methyl tetrahydropyridine-5-substituted indole and preparation method and application thereof

A technology of heterocyclic methyltetrahydropyridine linkage and indole, which can be applied in the fields of organic chemistry, drug combination, antitumor drugs, etc., and can solve the problem of few drug candidates.

Inactive Publication Date: 2013-08-07
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the number of new anti-cancer drugs on the market in my country and the number of candidate drugs in preclinical research is very small, and the number of candidate drugs with my country's independent intellectual property rights is even smaller

Method used

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  • N-heterocyclic methyl tetrahydropyridine-5-substituted indole and preparation method and application thereof
  • N-heterocyclic methyl tetrahydropyridine-5-substituted indole and preparation method and application thereof
  • N-heterocyclic methyl tetrahydropyridine-5-substituted indole and preparation method and application thereof

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Experimental program
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Embodiment 1～12

[0029] Embodiments 1-12 The preparation method of general formula (I) N-heterocyclic methyltetrahydropyridine-5-substituted indole is as follows:

[0030] At room temperature, dissolve the substituted heterocyclic primary amine (0.04mol) (1) in 4mL of methanol solution, add dropwise into the mixed solution of methyl acrylate (0.16mol) and methanol (7mL) under stirring, the temperature of the reaction system does not exceed 50 ℃. After the dropwise addition is completed, heat to reflux for another 7 to 8 hours, the reflux temperature is 65 to 75°C, and the reaction progress is tracked by thin layer chromatography (TLC). After the reaction, methanol and unreacted methyl acrylate were recovered and distilled under reduced pressure to obtain light yellow oily liquid (2).

[0031] Dissolve (2) (0.04mol) in anhydrous toluene (20mL) mixture, add dropwise under stirring, into anhydrous toluene (15mL) and metal sodium (0.122mol) solution, after dropwise addition, reflux for 6-8h. Dur...

Embodiment 13

[0034] Example 13-(N-(2-pyridylmethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (Ia)

[0035] Yield: 60%; yellow crystals; melting point: 160-162°C; 1 H NMR (400MHz, DMSO-d 6 )δ11.10(s, 1H), 7.79(d, J=8.0Hz, 1H), 7.56-6.78(m, 8H), 6.11(s, 1H), 3.67(s, 2H), 3.02(s, 2H ), 2.65 (t, J=5.5Hz, 2H), 2.49 (s, 2H); 820, 760cm -1 ;Anal.calcd.for C 19 h 19 N 3 C% 78.86, H% 6.62, N% 14.52; Found: C% 78.75, H% 6.90, N% 14.60.

Embodiment 23

[0036] Example 23-(N-(3-pyridylmethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (Ib)

[0037] Yield: 60%; yellow crystals; melting point: 166-168°C; 1 H NMR (400MHz, DMSO-d 6)δ11.08(s, 1H), 7.71(d, J=8.0Hz, 1H), 7.52-6.73(m, 8H), 6.13(s, 1H), 3.66(s, 2H), 3.01(s, 2H ), 2.62(t, J=5.5Hz, 2H), 2.49(s, 2H); IR(KBr): 3072, 3067, 2918, 2842, 1657, 1608, 1580, 1510, 1310, 1293, 1102, 940, 820, 760cm -1 ;Anal.calcd.for C 19 h 19 N 3 C% 78.86, H% 6.62, N% 14.52; Found: C% 78.70, H% 6.96, N% 14.62.

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Abstract

The invention discloses a N-heterocyclic methyl tetrahydropyridine-5-substituted indole and preparation method and application thereof, and the structure is shown in the general formula (I): heterocyclic methylamine and methyl acrylate are raw materials, and an intermediate N-heterocyclic methyl-4-piperidone is obtained by three steps of reaction such as Michael addition, Dieckmann condensation and hydrolysis decarboxylation or the like in sequence, and the object (I) is obtained by condensation reaction of the intermediate and 5-substituted indole. The compound (I) can effectively inhibit propagation of cell lines such as human leukemia K562, Jurkat, U937, THP-1; human esophagus cancer ECA-109; human liver cancer SMMC-7721; human ovary cancer HO-8910; human breast cancer MCF-7 and breast cancer MDA-MB-231; the compound inhibits the propagation of cancer cells by promoting cancer cell apoptosis. The compound can be applied to preparation of anticancer medicament.

Description

technical field [0001] The present invention relates to a class of lead compounds of anticancer drugs with high efficiency, wide anticancer spectrum and stable metabolism: N-heterocyclic methyltetrahydropyridine-5-substituted indole and N-heterocyclic methyltetrahydropyridine Preparation method and application of even-5-substituted indole. technical background [0002] According to the estimation of the World Health Organization, there are more than 3 million cancer patients in my country, and the rate of increase is 3% per year, and the trend is younger. For example, leukemia, a blood cell cancer, is more likely to occur in adolescents, and its incidence rate ranks first among adolescent tumors, so its harm to humans is more obvious and prominent. Due to the large number of patients with HBV hepatitis and related post-hepatitic cirrhosis in my country, the morbidity and mortality of liver cancer are significantly higher than the world average level, and more than 50% of gl...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D405/14A61K31/4545A61K31/454A61P35/00
Inventor 孙传文郝志兵肖笛薛思佳
Owner SHANGHAI NORMAL UNIVERSITY
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