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Phenothiazines and their preparation methods and applications

A technology of phenothiazines and compounds, applied in the field of anticancer drugs, can solve the problems of tumor recurrence and metastasis, and achieve the effects of high yield and simple synthesis method

Inactive Publication Date: 2018-07-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Cancer stem cells (CSC: CancerStemCell) refer to a small subset of cells (about 0.1%-5%) in tumor cells, which have characteristics similar to stem cells, such as self-renewal, unlimited proliferation, and high tumorigenicity. Most are dormant (G 0 ), has strong drug resistance, and traditional chemotherapy or radiotherapy cannot kill it, eventually leading to tumor recurrence and metastasis

Method used

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  • Phenothiazines and their preparation methods and applications
  • Phenothiazines and their preparation methods and applications
  • Phenothiazines and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation 2-21-2

[0029]

[0030] 2-10:

[0031] Take 2-trifluoromethylphenothiazine (2.00g, 7.4831mmol) and place it in a 500mL flask, add 2 CO 3 Dry THF (100mL), then in N 2 Under protection, 60% NaH mineral oil (1.1973 g, 29.9323 mmol) and 1-bromo-3-chloropropane (2.9601 mL, 29.9323 mmol) were sequentially added, and the mixture was refluxed overnight at a bath temperature of 65°C. Cool to room temperature, then pour the reaction solution into an ice-water mixture, extract with ethyl acetate (300mL+100mL×2), combine the organic phases, wash with anhydrous MgSO 4 Dry, filter to remove the solid, then spin the filtrate to dryness, add ethyl acetate (50mL) to dissolve, add silica gel powder (20g) to the solution and spin dry, dry load the sample through a silica gel column for purification, use ethyl acetate and petroleum ether After gradient elution, the product was collected, spin-dried, and vacuum-dried to obtain product 2-10 (4.9444 g, yield 69....

Embodiment 2

[0034] Example 2: Preparation 2-21-6

[0035]

[0036] In a 30mL straight bottle, add 2-10 (250mg, 0.7272mmol), prolinol (110.3mg, 1.0908mmol), triethylamine (0.5mL) and acetonitrile (10mL), and stir overnight at 80°C. Cool to room temperature, spin dry directly, dissolve the crude product in methanol, filter, add silica gel powder to the filtrate to make a solid solution, dry load the sample through a silica gel column for purification, and shower with triethylamine, ethyl acetate and petroleum ether gradient After washing, the product was collected, spin-dried, and vacuum-dried to obtain product 2-21-6 (138.9 mg, yield 38.9%). 1 H-NMR (400MHz, CDCl 3 )δ7.25-7.13(m,4H),7.05(s,1H),7.01-6.89(m,2H),4.05-3.96(m,2H),3.68-3.60(m,1H),3.51-3.42( m,1H),3.33-3.23(m,1H),3.14-3.03(m,1H),2.81-2.69(m,1H),2.61-2.50(m,1H),2.35-2.24(m,1H), 2.16-2.05(m,2H),1.85-1.72(m,3H),1.28-1.23(m,2H);+c ESI Q1MS: [M+H +] 409.11.

Embodiment 3

[0037] Example 3: Preparation of 2-163, 2-172

[0038]

[0039] 2-21-1:

[0040] Take 2-10 (300mg, 0.8726mmol) and place it in a 30mL straight bottle, then add 1-tert-butoxycarbonylpiperazine (243.8mg, 1.3089mmol), triethylamine (0.37ml, 2.6178mmol) and acetonitrile (10mL) , react overnight at 80°C. Cool to room temperature, directly evaporate to dryness, dissolve the crude product in methanol, then add silica gel powder to the filtrate to make a solid solution, dry load the sample through a silica gel column for purification, and use gradient elution with ethyl acetate, petroleum ether and triethylamine , collected the product, spin-dried, and vacuum-dried to obtain the product 2-21-1 (63.4 mg, yield 40.2%). 1 H-NMR (400MHz, CDCl 3 )δ7.24-7.10(m,5H),7.04(s,1H),7.00-6.88(m,1H),4.08-3.95(m,2H),3.60-3.25(m,4H),2.70-2.25( m,6H),2.12-1.90(m,2H),1.44(s,9H);+c ESI Q1MS: [M+H + ] 494.20.

[0041] 2-163:

[0042] In a 100 mL flask, 2-21-1 (2.4458 g, 4.9569 mmol) was dissolve...

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Abstract

The invention relates to a phenothiazine compound and a preparation method thereof. The invention further relates the application of the phenothiazine compound in anti-cancer drug preparation and anti-cancer drugs using the compound as the effective component. The phenothiazine compound has the advantages that the compound with broad-spectrum anti-cancer effect is obtained by modifying phenothiazine ternary interlink parent nucleuses, synthesizing method is simple, and high yield is achieved; the phenothiazine compound has certain restraining effect on human breast cancer cells line MCF-7 and human hepatoma cell line Hep-G2, and a new thought is provided to new drugs satisfying clinic requirements.

Description

technical field [0001] The invention belongs to the field of anticancer drugs, and relates to a phenothiazine compound with anticancer effect and a preparation method of the compound. In addition, the invention also relates to the application of the compound in the preparation of anticancer drugs, and the compound containing the phenothiazine Compounds as active ingredients of anticancer drugs. Background technique [0002] Over the past 20 years, cancer stem cells from various solid tumors and blood cancers have been isolated one after another. Cancer stem cells (CSC: CancerStemCell) refer to a small subset of cells (about 0.1%-5%) in tumor cells, which have characteristics similar to stem cells, such as self-renewal, unlimited proliferation, and high tumorigenicity. Most are dormant (G 0 ), has strong drug resistance, and traditional chemotherapy or radiotherapy cannot kill it, eventually leading to tumor recurrence and metastasis. Since the Whitehead Institute of Harva...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/28C07D417/06C07D279/22A61K31/5415A61P35/00
CPCC07D279/22C07D279/28C07D417/06
Inventor 李高全谢爱云张翠芳陈毛芬
Owner DALIAN UNIV OF TECH
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