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S-triazolo-thiadiazole and thiadiazine derivatives, preparation method and application thereof
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A technology of thiadiazines and derivatives, applied in the field of medicine, can solve the problems that have not yet been seen
Inactive Publication Date: 2015-10-28
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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The anti-mycobacterium tuberculosis effect of the s-triazolothiadiazole and thiadiazine derivatives with MtSD as the target of the present invention has not been reported so far at home and abroad.
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Embodiment 1
[0069] "Example 1" 3-(4-fluorophenyl)-6-(phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadi The synthesis of azole (compound 1 is: IMB-CC223) is divided into the following steps:
[0070] 1) Synthesis of p-fluorobenzoic hydrazide (intermediate 3)
[0071] Add p-fluorobenzoic acid (10.0g, 60mmol) and 100mL tetrahydrofuran in a 250mL three-necked flask, then add N,N'-carbonyldiimidazole (12.6g, 78mmol), TLC monitors whether the reaction of the raw materials is complete, after the completion of the reaction, slowly 80% hydrazine hydrate (5.94 g, 95 mmol) was added dropwise, and the reaction was stirred for about 6 hours after the drop was completed. TLC monitors whether the reaction of raw materials is complete (developing solvent: petroleumether / ethyl acetate 1:1). After completion of the reaction, cool to room temperature, concentrate under reduced pressure to remove most of the organic solvent, add about 30 mL of water, beat at room temperature for a while, filter with suct...
Embodiment 2
[0078] "Example 2" 3-(4-chlorophenyl)-6-(4-bromophenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4 Synthesis of ]thiadiazole (compound 2)
[0079] Change p-fluorobenzoic acid into 2-naphthylacetic acid, and phenoxyacetic acid into p-nitrophenoxyacetic acid, and use a method similar to "Example 1" to obtain 3-(2-naphthylmethyl)-6-(4- Nitrophenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (Compound 2). 1 H NMR (500MHz, DMSO-d6) δ8.27–8.21(m,3H),7.97–7.93(m,1H),7.86(d,J=7.7Hz,1H),7.55(m,2H),7.46– 7.40 (m, 2H), 7.31–7.27 (m, 2H), 5.70 (s, 2H), 4.87 (s, 2H). HRMS-APCI: Calculated C 21 h 15 N 5 o 3 S[M+H] + : 418.0968; actual value: 418.0953.
Embodiment 3
[0080]"Example 3" 3-(4-fluorophenyl)-6-(4-methoxyphenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3 ,4] Synthesis of Thiadiazole (Compound 3)
[0081] Phenoxyacetic acid is replaced with p-methoxyphenoxyacetic acid, and a method similar to "Example 1" is used to obtain 3-(4-fluorophenyl)-6-(4-methoxyphenoxymethyl)-[ 1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (Compound 3). 1 H NMR (400MHz, DMSO-d6) δ8.26(d, J=8.8Hz, 2H), 7.48(d, J=8.8Hz, 2H), 7.08(d, J=9.0Hz, 2H), 6.91(d , J=9.0Hz, 2H), 5.56(s, 2H), 3.71(s, 3H). HRMS-APCI: Calculated C 17 h 13 FN 4 o 2 S[M+H] + : 357.0816; actual value: 357.0823.
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Abstract
The invention relates to S-triazolo-thiadiazole and thiadiazine derivatives and an application thereof. Research results show that, the minimal inhibitory concentration (MIC) of the derivatives to mycobacteriumtuberculosis standard strains H37Rv is 0.25 [mu]g / mL, and the inhibitory activities of the derivatives to isoniazide / rifampicin-resistant mycobacteriumtuberculosis (MDRTB) and rifampicin-resistant mycobacteriumtuberculosis (RDRTB) are the same and the MIC of the derivatives to MDRTB and RDRTB is 0.25-4 [mu]g / mL. Meanwhile, the resistance of some derivatives to MDRTB or RDRTB is better than the resistance of the derivatives to reference drugs RIF and INH. At the same time, most derivatives are equivalent in inhibitory activity to Shikimate dehydrogenase, thus being good in development prospect.
Description
Technical field: [0001] The invention belongs to the field of medicine, and relates to two types of s-triazolothiadiazole and thiadiazine derivatives and their preparation methods and applications. Background technique: [0002] Tuberculosis is a chronic infectious disease caused by Mycobacterium tuberculosis infection. It has been harmful to humans for thousands of years and is a public health and social problem of global concern. In the early 1980s, due to the development of short-course chemotherapy for tuberculosis, tuberculosis was controlled to a large extent. But in recent years, with the increase of multi-drugresistant tuberculosis and AIDS patients, the third tuberculosis rebound has appeared in the world, and the tuberculosis epidemic situation is showing a serious situation of comeback. According to the latest statistics from the World Health Organization, there are more than 8.8 million new cases of tuberculosis and 1.4 million deaths each year worldwide, makin...
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