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Anti-cancer compound as well as preparation method and application thereof

A compound and low-level technology, applied in organic chemistry, antiviral agents, antitumor drugs, etc., can solve problems such as toxicity, ataxia, and disorientation, and achieve significant anticancer effects and good anticancer effects

Pending Publication Date: 2020-06-19
天津孚音生物科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] So far, the best anticancer effect of PBTs compounds is the compound 21 (as shown in formula D) reported in the literature J.Med.Chem. There is a certain gap between the phenanthrene and indolizidine alkaloid compound (-)-Antofine (as shown in formula D), (-)-antofine is right to half of the cancer cells of lung cancer, prostate cancer, breast cancer and nasopharyngeal carcinoma The worst inhibitory concentration (IC50) is 0.036 μM, but it also exhibits central nervous system toxicity (such as disorientation and ataxia) like other phenanthrene indolizidine alkaloids

Method used

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  • Anti-cancer compound as well as preparation method and application thereof
  • Anti-cancer compound as well as preparation method and application thereof
  • Anti-cancer compound as well as preparation method and application thereof

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preparation example Construction

[0100] For the preparation method of the compound of formula I, refer to patent CN103664977A, and for the preparation method of the compound of formula V, refer to the literature J.Med.Chem.2009, 52, 5262-5268.

[0101] Method Two:

[0102] Step 1: Mannich reaction of the compound of formula I with piperazine and formaldehyde (formaldehyde aqueous solution or formaldehyde polymer) under acidic conditions to prepare the compound of formula VII;

[0103] Step 2: Nucleophilic substitution reaction between the compound of formula VII and the compound of formula VI under alkaline conditions to generate the compound of formula M;

[0104] Step 3: the compound of formula M and the compound of formula III react under heating conditions to generate the compound of formula N;

[0105] The synthesis path is as follows:

[0106]

[0107] The specific preparation method is:

[0108] Step 1: Mannich reaction of the compound of formula I with piperazine and formaldehyde (aqueous formalde...

Embodiment 1

[0127] Embodiment 1: the preparation of compound NA1

[0128]

[0129] 1.1 Preparation of compound IIA1:

[0130] Add ethanol (10mL), compound IA1 (1g), 1-benzyloxycarbonylpiperazine (1.48g), and paraformaldehyde (0.37g) into the reaction flask in turn, add concentrated hydrochloric acid (0.5mL) under stirring, and heat to 70 ℃, stirred until compound IA1 reacted completely, concentrated under reduced pressure to remove most of the ethanol, precipitated solid, filtered with suction, washed the solid with methyl tert-butyl ether, dissolved the solid in water, added saturated sodium bicarbonate to adjust the pH value to ≈8 , extracted with methyl tert-butyl ether, the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain crude compound IIA1 (2.12 g), which was directly cast down. LCMS(ESI): 395.1[M+H] + .

[0131]Add methanol (10mL), compound IA1 (1g), 1-benzyloxycarbonylpiperazine (2.01g), and paraformaldehyde...

Embodiment 2

[0151] The preparation of embodiment 2 compound NA58, NA59

[0152]

[0153] 2.1 Preparation of compound VIIA:

[0154] Add ethanol (10mL), compound IA (1.37g), piperazine (1.06), and paraformaldehyde (0.37g) into the reaction flask in turn, add concentrated hydrochloric acid (0.5mL) while stirring, heat to 70°C, and stir until the compound 1 After the reaction is complete, concentrate most of the ethanol under reduced pressure, precipitate the solid, filter it with suction, wash the solid with methyl tert-butyl ether, dissolve the solid in water, add saturated sodium bicarbonate to adjust the pH value to ≈8, and use methyl tert-butyl ether Extract with butyl ether, combine the organic layers, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain compound VIIA (1.38 g), which is directly cast down. LCMS(ESI): 321.1[M+H] + .

[0155] Add methanol (10mL), compound IA (1.37g), piperazine (1.06), and paraformaldehyde (0.74g) into the reaction fl...

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Abstract

The invention relates to an anti-cancer compound as well as a preparation method and application thereof. The anti-cancer compound is obtained by connecting a pyrazole compound with a PBTs (Polybutylene Terephthalate) compound and adding a hydrophilic group a pyrazole ring. The pyrazole compound is a nitrogen-containing heterocyclic compound and has the characteristics of high efficiency, low toxicity, unique action mechanism, safety, no cross resistance and the like. The prepared compounds have a remarkable anti-cancer effect, most of the compounds have better anti-cancer effects than (-)-Antofine, and the compounds have no obvious toxicity to animals and also have antiviral activity. The compound can be used for preparing medicines for preventing and / or treating cancers and / or resistingviruses.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to an anticancer compound and its preparation method and application. Background technique [0002] Azaphenanthrene-indolizidine and azaphenanthrene-quinolizidine alkaloids are a class of pentacyclic natural products isolated from plant families such as Romoaceae, Moraceae, Acanthaceae and Lauraceae. Since the first phenanthrene and indolizidine alkaloid, sylphine ((R)-tylophorine) (as shown in formula A), was isolated in 1935, numerous phenanthrene and indolizidine biological Bases are isolated or synthesized, and they have a wide range of biological activities, such as anti-cancer (anti-tumor), anti-leukemia, anti-inflammatory, anti-viral, anti-bacterial, anti-amoeba activities, etc. Among many biological activities, its unique Anticancer activity is of most interest. But at the same time, their toxicity to the central nervous system has largely influenced the deve...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61P35/00A61P31/12A61K31/496A61K31/5377
CPCC07D405/12A61P35/00A61P31/12Y02P20/55
Inventor 莫岚刘文娟于鹏飞
Owner 天津孚音生物科技发展有限公司
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