Benzotriazole compound, preparation method and medical application thereof
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A technology of benzotriazole and benzotriazole, applied in the field of medicine
Active Publication Date: 2016-01-06
EAST CHINA NORMAL UNIV
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However, so far there are no small molecule inhibitors that are effective in the treatment of RAS-mutated tumors.
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Embodiment 1
[0117] Embodiment one: the preparation of each compound
Embodiment 1-1
[0118] Example 1-1, 5-bromofuran-2-carboxylic acid [2-(4-methoxyphenyl)-2H-benzotriazol-5-yl]-amide (RS001)
[0119] Dissolve p-methoxyaniline (2.48g, 20.14mmol) in 48ml of aqueous hydrochloric acid solution (4M), add sodium nitrite (1.67g, 24.17mmol) under ice-bath conditions, and react for half an hour, then add sulfamic acid Ammonium (3.16g) was slowly added to the system at 0°C and stirring was continued for half an hour. The pH of the solution was adjusted to 5-6 with sodium acetate, and o-phenylenediamine hydrochloride (3.33 g, 18.42 mmol) was added to the reaction system under ice-bath conditions, and stirred overnight. After the completion of the reaction as detected by TLC, adjust the pH to greater than 14 with sodium hydroxide solution, extract with ethyl acetate and water, combine the organic phases, and distill under reduced pressure to obtain a dry crude azo compound. The azo compound was dissolved with 40ml of pyridine, and 10g of anhydrous copper sulfate was ad...
Embodiment 1-2
[0129] Example 1-2, Preparation of 5-bromofuran-2-carboxylic acid [2-(4-chlorophenyl)-2H-benzotriazol-5-yl]-amide (RS002)
[0130] Substitute p-methoxyaniline with 4-chloroaniline, and prepare RS002 according to the method for preparing compound RS001. 1 HNMR(DMSO,300MHz):δ10.51(s,1H),8.49(s,1H),8.27(d,J=8.7Hz,2H),8.98(dd,J=0.3,0.3Hz,1H),7.78 (t, J=0.9Hz, 1H), 7.71(s, 2H), 7.44(d, J=3.3Hz, 1H), 6.87(d, J=3.3Hz, 1H).
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Abstract
The invention discloses a benzotriazole small-molecule compound shown in structural formula (1) or pharmaceutically acceptable acid added salt of the compound and pharmaceutical composition containing the compound. The invention further discloses a medical application of the benzotriazole small-molecule compound or the pharmaceutically acceptable acid added salt of the compound to preparation of drugs for treating growth, transfer and recurrence of diseases such as various malignant tumors caused by RAS gene mutation.
Description
technical field [0001] The invention belongs to the field of medicine, and in particular relates to a class of small molecule benzotriazole compounds, pharmaceutically acceptable salts and their medical use. technical background [0002] Cancer has been threatening human health for a long time, and it is called the three major killers of human health together with diabetes and cardiovascular and cerebrovascular diseases. For cancer, the current main treatment methods are surgery, radiotherapy and chemotherapy. Although, for early cancer patients, the tumor can be removed by surgery, but after the middle and late stages, the cancer cells will spread, and the corresponding surgical resection method will not achieve a good therapeutic effect. [0003] With the rapid development of the Human Genome Project and sequencing technology, the complex genetic information of the tumor genome can be accurately obtained through whole-genome sequencing analysis of human tumor samples, and...
Claims
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