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Biphenylacylamine tetrazole compounds, synthetic method and application
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The technology of methyl biphenylamide tetrazole and compound, which is applied in the field of medicine, can solve the problem of low curative effect of endothelin receptor antagonists, and achieves the effects of novel chemical structure and easy availability of raw materials
Inactive Publication Date: 2012-07-04
BEIJING INSTITUTE OF TECHNOLOGYGY
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[0005] The purpose of the present invention is to provide a [[(2-n-propyl-4-methyl-1H-benzene Imidazolium)-6-yl]formamide-1-yl]methylbenzamide tetrazole compound, synthesis method and use
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Embodiment 1
[0021] Intermediate 4'-{[N-(morpholine ethyl)-[(2-n-propyl-4-methyl-1H-benzimidazol)-6-yl]formamide-1-yl]methyl }-[1,1′-Biphenyl]-2-carboxylate methyl ester: add 1mL N, N-dimethylformamide (DMF), N-(morpholine ethyl)- [(2-n-Propyl-4-methyl-1H-benzimidazol)-6-yl]formamide 80.2mg (0.245mmol), add potassium tert-butoxide 30.1mg (0.282mmol) under ice-water bath conditions , warmed up to room temperature, stirred for 30 minutes, then cooled down to 0°C, added 80.2mg (0.264mmol) of 2-carboxylate methyl-4'-bromomethylbiphenyl, and warmed up to room temperature for 3h reaction. After the reaction was completed, 10 mL of ethyl acetate was added for dilution, washed with saturated brine (3×10 mL), the organic layer was dried over anhydroussodiumsulfate, and the solvent was evaporated under reduced pressure to obtain 104.3 mg of the product as a colorless viscous substance with a yield of 65.1% . 1 H NMR (400MHz, CDCl 3 )δ: 0.95(t, J=7.18Hz, 3H), 1.74(m, 2H), 2.36(t, J=7.21Hz, 4H), 2...
Embodiment 2
[0023] The conditions are the same as in Example 1, and the intermediate 4'-{[N-(4-methylpiperazin-1-yl)ethyl)-[(2-n-propyl-4-methyl-1H-benzo imidazolium)-6-yl]formamido-1-yl]methyl}-[1,1'-biphenyl]-2-carboxylic acid methyl ester. 120.2 mg of a colorless viscous substance was obtained with a yield of 59.5%. 1 H NMR (400MHz, CDCl 3 )δ: 0.95(t, J=7.20Hz, 3H), 1.74(m, 2H), 2.30(s, 3H), 2.46(t, J=7.25Hz, 4H), 2.56(s, 3H), 2.67( t, J=7.22Hz, 4H), 2.78(t, J=7.16Hz, 2H), 2.83(t, J=7.15Hz, 2H), 3.48(m, 2H), 3.61(s, 3H), 5.56( s, 2H), 7.06-7.91 (m, 10H), 8.44 (s, 1H).
Embodiment 3
[0025] The conditions are the same as in Example 1, and the intermediate 4'-{[N-(piperidinyl)-[(2-n-propyl-4-methyl-1H-benzimidazole)-6-yl]formamide is prepared -1-yl]methyl}-[1,1'-biphenyl]-2-carboxylic acid methyl ester. 123.1 mg of a colorless viscous substance was obtained with a yield of 61.4%. 1 H NMR (400MHz, CDCl 3)δ: 0.94(t, J=7.24Hz, 3H), 1.58(m, 6H), 1.75(m, 2H), 2.40(t, J=7.19Hz, 4H), 2.55(s, 3H), 2.78( t, J=7.22Hz, 2H), 2.85(t, J=7.15Hz, 2H), 3.49(m, 2H), 3.61(s, 3H), 5.56(s, 2H), 7.10~7.94(m, 10H ), 8.45(s, 1H).
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Abstract
The invention relates to [[(2-n-propyl-4-methyl-1H-benzimidazole)-6-yl] formamide-1-yl] methyl biphenylacylamine tetrazole compounds, a synthetic method and application, and belongs to the technical field of medicaments. The structural formula of the compound is shown in the specification, wherein R1 is the [[(2-n-propyl-4-methyl-1H-benzimidazole)-6-yl] formamide-1-yl] methyl biphenylacylamine tetrazole compounds, and M is hydrogen, potassium or sodium. Experiments prove that the compounds have the excellent dual antagonist activity of an angiotensin IIreceptor and an endothelin receptor, and can be used for preparing medicaments for treating cardiovascular and cerebrovascular diseases.
Description
technical field [0001] The invention relates to the field of medical technology, and is a novel and simple [[(2-n-propyl-4-methyl-1H- Benzimidazole)-6-formamido-1-yl]methylbenzamide tetrazole compound and its synthesis method are used as medicine for treating cardiovascular and cerebrovascular diseases. Background technique [0002] Cardiovascular disease has a high incidence rate and many and serious complications, which seriously threaten human health. Non-peptide angiotensin AT1 receptor blockers (ARBs) are a new class of antihypertensive drugs that act on the renin-angiotensin system (RAS). Compared with angiotensin-converting enzyme inhibitors (ACEIs), The antihypertensive effect is more significant, the RAS is more selectively blocked, and the side effects are small, and it has been listed as one of the six major antihypertensive drugs. [0003] The renin-angiotensin system plays an important role in regulating blood pressure, body fluid balance and dielectric balanc...
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