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Substituted mercapto six-membered aromatic heterocyclic imidazole derivatives and its preparation method and application

A technology of derivatives and aromatic heterocycles, applied in the field of medicine, can solve problems such as endangering human life and health, and unsatisfactory treatment effects

Active Publication Date: 2015-10-21
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are dozens of anti-tumor drugs commonly used clinically, the treatment of solid tumors, which is the most serious threat to human life and health and accounts for more than 90% of malignant tumors, has not achieved satisfactory results.

Method used

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  • Substituted mercapto six-membered aromatic heterocyclic imidazole derivatives and its preparation method and application
  • Substituted mercapto six-membered aromatic heterocyclic imidazole derivatives and its preparation method and application
  • Substituted mercapto six-membered aromatic heterocyclic imidazole derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Example 1: 1-(3,4-dihydroxyphenyl)-2-(3-(2,4,6-trimethylbenzene)-3H-imidazo[4,5-b]pyridine-2-mercapto ) ethyl ketone (CHEQ-1, Ar 1 =2,4,6-Trimethylphenyl) Preparation

[0081] 20 mL of 1,2,-dichloroethane solution was cooled to 5-10°C, aluminum trichloride (6.0 g, 45 mmol) was added slowly, and the mixture was stirred at 5-10°C for 30 minutes. Then slowly add catechol (a1, R 2X =R 3X =R 6X =H) (2.0 g, 18.1 mmol), the addition was complete and the reaction was stirred at this temperature for 20 minutes. Chloroacetyl chloride (2.2 g, 19.3 mmol) was then added dropwise, keeping the temperature at 5-10°C. After the addition, the temperature was raised to room temperature and stirred for about 20 hours. TLC detected that the reaction was complete, slowly added 40 mL of dilute hydrochloric acid solution at 5-10°C, and stirred at room temperature for 2-3 hours. The solid precipitated, was suction filtered, washed with water, the undried solid was suspended in dilute ace...

Embodiment 2

[0083] Example 2: 1-(3,4-dihydroxyphenyl)-2-(1-(2,4,6-trimethylbenzene)-1H-imidazo[4,5-c]pyridine-2-mercapto ) ethyl ketone (CHEQ-2, Ar 1 =2,4,6-Trimethylphenyl) Preparation

[0084] The operation method is the same as the preparation of CHEQ1 in Example 1, except that 1-(2,4,6-trimethylphenyl)-1H-imidazol[4,5-c]pyridine-2-mercapto (PDMZ2SH, Ar 1 =2,4,6-trimethylphenyl). The obtained product is off-white powder, 0.28g, yield: 67%; melting point: 256-258°C. 1 H NMR (400MHz, DMSO-d6, ppm) δ: 9.78 (2H, brs), 8.88 (1H, s, C 4 -imidazo[4,5-c]pyridine-H), 8.26 (1H,d,J=4.8Hz,C 6 -imidazo[4,5-c]pyridine-H),7.49(1H,dd,J=1.5,8.2Hz,C 6 -Ph'-H),7.41(1H,s,C 2 -Ph'-H),7.19(2H,s,C 3,5 -Ph-H),6.97(1H,d,J=4.8Hz,C 7 -imidazo[4,5-c]pyridine-H),6.86(1H,d,J=8.2Hz,C 5 -Ph'-H),5.03(2H,s,S-CH 2 ),2.38(3H,s,Me),1.88(6H,s,2×Me).MS(ESI):m / z420.3(M+1).C 23 h 21 N 3 o 3 S(419.13).

Embodiment 3

[0085] Example 3: N-(2-aminophenyl)-2-(1-(2,4,6-trimethylbenzene)-1H-imidazo[4,5-c]pyridine-2-mercapto)acetamide (CHEQ-3, Ar 1 =2,4,6-trimethylphenyl,R 3X =R 4X =R 5X =R 6X =H) Preparation

[0086] 2-nitroaniline (b3, R 3X =R 4X =R 5X =R 6X =H) (2.0 g, 14.5 mmol) was dissolved in dichloromethane (15 mL), then triethylamine (2.5 mL, 17.4 mmol) was added and stirred for 10 minutes. Then slowly add 10 mL of dichloromethane solution of chloroacetyl chloride (1.38 mL, 17.4 mmol) dropwise into the above solution, stir at room temperature for 3 hours, add 10 mL of ice water, wash the organic phase with water (30 mL), and extract the aqueous phase with dichloromethane (3×15mL), the organic phases were combined, dried over anhydrous sodium sulfate, suction filtered, and concentrated under reduced pressure to obtain 2-chloro-N-(2-nitrophenyl)acetamide (b4, R 3X =R 4X =R 5X =R 6X =H), yellow crystals, yield: 83.6%, the purity is enough to carry out the next reaction directly...

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Abstract

The invention relates to a substituted sulfydryl hexahydric heteroaromatic imidazole derivative shown in formula I or II or a pharmaceutically acceptable salt thereof and also relates to a preparation method of the compound as shown in the formula I or II, a pharmaceutical composition containing the compound, and application of the compound in preparation of an antineoplastic drug.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to substituted mercapto six-membered aromatic heterocyclic imidazole derivatives or pharmaceutically acceptable salts thereof, a preparation method thereof, a pharmaceutical composition containing the compound and its application in the pharmaceutical industry. Application in the preparation of antitumor drugs. Background technique [0002] Malignant tumors are common and frequently-occurring diseases that seriously threaten human health and survival. According to the report of the World Health Organization, tens of millions of patients die from cancer every year in the world, and the number of people who die and get sick from cancer will continue to increase in the future. Among the three major therapies for malignant tumors (surgery, chemotherapy, and radiotherapy), drug therapy plays an important role. Although there are dozens of anti-tumor drugs commonly used cli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/437A61P35/00
CPCC07D471/04
Inventor 展鹏刘新泳宋宇宁康东伟张庆柱
Owner SHANDONG UNIV
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