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Benzothiazole-oxazole type alpha-glucosidase inhibitor and preparation method and application thereof

A technology of glucosidase and benzothiazole, which is applied in the fields of metabolic diseases, organic chemistry, drug combination, etc., can solve the problems of low production cost and high production cost, achieve high-efficiency inhibitory activity, simple preparation process, and mild reaction conditions.

Active Publication Date: 2018-09-14
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Production cost is higher, so developing a kind of production cost is low, the α-glucosidase inhibitor with high inhibitory activity is the problem that those skilled in the art need to solve urgently

Method used

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  • Benzothiazole-oxazole type alpha-glucosidase inhibitor and preparation method and application thereof
  • Benzothiazole-oxazole type alpha-glucosidase inhibitor and preparation method and application thereof
  • Benzothiazole-oxazole type alpha-glucosidase inhibitor and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 2-(benzothiazol-2-yl)-5-phenyloxazole (1)

[0023] Step 1: Put benzothiazole-2-carbaldehyde (1.63g, 10mmol) and hydroxylamine hydrochloride (1.04g, 15mmol) in a round bottom flask, add 100ml of 50% methanol aqueous solution, and add 6ml of sodium carbonate aqueous solution (0.75M ), after the addition is complete, the reaction is stirred at room temperature for 5 hours, spin-dried, and separated and purified by silica gel column chromatography to obtain a solid powder with a yield of 87%.

[0024] Step 2: Put benzothiazole-2-carbaldehyde oxime (1.78g, 10mmol), zinc powder (0.98g, 15mmol), ammonium formate (1.26g, 20mmol) in a round bottom flask, add 100ml methanol, and react under reflux 2. After hours, the reaction was stopped, poured into water, extracted with ethyl acetate, combined organic phases, spin-dried, and separated and purified by gel column chromatography to obtain a solid powder with a yield of 93%.

[0025] Step 3: Put benzothiazol-2-y...

Embodiment 2

[0029] Preparation of 2-(benzothiazol-2-yl)-5-(3-fluorophenyl)oxazole (2)

[0030] The preparation method is the same as in Example 1, the product structure is as follows, and the yield is 61%.

[0031]

[0032] 1 H NMR(CDCl 3 ,400MHz)δ: 7.10(s,1H),7.22-7.23(m,1H),7.51-7.54(m,4H),7.84-7.85(m,1H),8.02(d,1H), 8.18(d, 1H); EIMS m / z=297[M + ].

Embodiment 3

[0034] Preparation of 3-(benzothiazol-2-yl)-5-(3,4,5-trimethoxyphenyl)oxazole (3)

[0035] The preparation method is the same as in Example 1, the product structure is as follows, and the yield is 58%.

[0036]

[0037] 1 H NMR(CDCl 3 ,400MHz)δ: 3.75(s,3H), 3.85(s,6H), 6.99(s,2H), 7.10(s,1H), 7.51-7.52(m,2H), 8.02(d,1H), 8.18 (d,1H); EIMS m / z=369[M + ].

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Abstract

The invention discloses a benzothiazole-oxazole type alpha-glucosidase inhibitor and a preparation method and application thereof. The method comprises the following steps: adding a compound (II) andhydroxylamine hydrochloride in a methanol aqueous solution and a sodium carbonate aqueous solution to obtain a compound (III); adding the compound (III), zinc powder and ammonium formate in methanol and reacting to obtain a compound (IV); and adding the compound (IV), a compound (V), iodine and potassium carbonate in DMF and reacting to obtain a compound (I). The chemical formula of the compound (I) is as shown in specification, the chemical formula of the compound (II) is as shown in specification, the chemical formula of the compound (III) is as shown in specification, the chemical formula of the compound (IV) is as shown in specification, and the chemical formula of the compound (V) is as shown in specification. The benzothiazole-oxazole type compound has obvious inhibition effect on alpha-glucosidase, the preparation method is simple, reaction conditions are gentle, and thus, the benzothiazole-oxazole type alpha-glucosidase inhibitor is suitable for being industrially produced on alarge scale.

Description

Technical field [0001] The invention relates to a benzothiazole-oxazole type compound, a preparation method thereof, and application as an α-glucosidase inhibitor in anti-diabetic medicine. Background technique [0002] Diabetes is a metabolic disease characterized by hyperglycemia. The disease has become a global health problem. This disease not only has long-term complicated complications in major organs, but also brings a huge economic burden to the patient's family. The main method of treating this disease is to reduce the concentration of blood sugar, thereby preventing the complicated pathological changes of the capillaries and large vessels. Alpha-glucosidase is one of the main enzymes in the digestion of carbohydrates such as dextrin and starch. This enzyme can catalyze the hydrolysis of carbohydrates, causing it to release glucose, thereby increasing blood sugar after a meal. Alpha-glucosidase inhibitors are of great significance to delay the digestion of carbohydrate...

Claims

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Application Information

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IPC IPC(8): C07D417/04A61P3/10
CPCA61P3/10C07D417/04
Inventor 王广成彭知云李勇军巩仔鹏马雪
Owner GUIZHOU MEDICAL UNIV
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