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1, 2-benzothiazine heterocyclic derivative as well as preparation method and application thereof

A technology for benzothiazine and derivatives, which is applied in the field of 1,2-benzothiazine heterocyclic derivatives and their preparation, and achieves the effects of improving binding capacity, increasing strength, and improving antitumor activity

Active Publication Date: 2021-10-22
齐鲁医药学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] How to improve the anti-tumor activity of 1,2-benzothiazine ring in piroxicam, reduce the adverse reactions of anti-tumor drugs, and make the clinical application of the drug more extensive , so far no relevant literature or patents have been found to report

Method used

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  • 1, 2-benzothiazine heterocyclic derivative as well as preparation method and application thereof
  • 1, 2-benzothiazine heterocyclic derivative as well as preparation method and application thereof
  • 1, 2-benzothiazine heterocyclic derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 26.880g 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid methyl ester-1,1-dioxide, 18mL80wt.% hydrazine hydrate solution, 110mL absolute ethanol Add it into a 250mL three-neck flask, heat and reflux for 12 hours to obtain a yellow clear solution; distill off the solvent under reduced pressure to obtain a light yellow viscous substance, then add 40mL of absolute ethanol, heat to dissolve completely, cool naturally, filter, Collect the filter cake and blow dry at 50°C to obtain a yellow solid 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxhydrazide-1,1-dioxide 23.044 g, the yield is 85.73%.

[0040] Weigh 6g (0.087mol) of potassium hydroxide and dissolve it in 150mL of absolute ethanol. After completely dissolving, add 15g (0.055mol) of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3- Forformylhydrazide-1,1-dioxide, cool down to about 0°C in an ice bath, control the temperature at 0-5°C, add 6mL of carbon disulfide with a concentration of 1.26g / ml dropwise with a con...

Embodiment 2

[0042] Add 40.064g of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid methyl ester-1,1-dioxide, 28mL of 80wt.% hydrazine hydrate solution, and 160mL of methanol to In a 250mL three-neck flask, heat and reflux for 12 hours to obtain a yellow clear solution; distill off the solvent under reduced pressure to obtain a light yellow viscous substance, then add 60mL of absolute ethanol, and heat to completely dissolve, naturally cool, filter, and collect the filtered cake, and air-dried at 50°C to obtain 33.714g of yellow solid 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxhydrazide-1,1-dioxide, The yield is 84.15%.

[0043] Take 10g (0.146mol) of potassium hydroxide and dissolve it in 135mL of absolute ethanol. After completely dissolving, add 26.9g (0.1mol) of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3- Formohydrazide-1,1-dioxide, cool down to about 0°C in an ice bath, control the temperature at 0-5°C, slowly add 9mL of carbon disulfide with a concentration of 1.26g / ml ...

Embodiment 3

[0046] 26.880g 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid methyl ester-1,1-dioxide, 25mL80wt.% hydrazine hydrate solution, 150mL n-propanol Add it into a 250mL three-neck flask, heat and reflux for 12 hours to obtain a yellow clear solution; distill off the solvent under reduced pressure to obtain a light yellow viscous substance, then add 50mL of n-propanol, heat to dissolve completely, cool naturally, filter, Collect the filter cake and blow dry at 50°C to obtain a yellow solid 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxhydrazide-1,1-dioxide 23.453 g, the yield is 87.25%.

[0047] Weigh 6g (0.087mol) of potassium hydroxide and dissolve it in 145mL of n-propanol. After completely dissolving, add 15g (0.055mol) of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3- Formohydrazide-1,1-dioxide, cool down to about 0°C in an ice bath, control the temperature at 0-5°C, add 9mL of carbon disulfide with a concentration of 1.26g / ml dropwise through a constant pressure drop...

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Abstract

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a 1, 2-benzothiazine heterocyclic derivative, the structural formula of which is formula I or formula II: a thiadiazole (oxadiazole) ring is introduced to the C-3 site of a 1, 2-benzothiazine ring, so that the 1, 2-benzothiazine heterocyclic derivative has higher anti-tumor activity, and the occurrence of adverse reaction is reduced; and the invention also provides a preparation method and application of the 1, 2-benzothiazine heterocyclic derivative. A thiadiazole (oxadiazole) ring is introduced to the C-3 site of a 1, 2-benzothiazine ring, and the obtained 1, 2-benzothiazine heterocyclic ring derivative has high anti-tumor activity, can be used as an anti-tumor drug, and has a wider research prospect in the aspect of tumor treatment.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a 1,2-benzothiazine heterocyclic derivative and a preparation method and application thereof. Background technique [0002] Piroxicam, whose chemical formula is as follows, has analgesic, anti-inflammatory and antipyretic effects. The drug belongs to non-steroidal anti-inflammatory drugs, and its core is 1,2-benzothiazine ring. Piroxicam exerts its pharmacological effects by inhibiting the activity of cyclooxygenase, reducing the synthesis of prostaglandins, inhibiting the chemotaxis of leukocytes and the release of lysosomes. The drug selectively inhibits the activity of COX-2, and its adverse reactions are mainly gastrointestinal reactions, and food can also reduce the absorption rate of the drug. [0003] [0004] How to improve the anti-tumor activity of the 1,2-benzothiazine ring in piroxicam, reduce the adverse reactions of anti-tumor drugs, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A61P35/00
CPCC07D417/04A61P35/00
Inventor 赵小美王新汲霞张华董俊泽宿正文
Owner 齐鲁医药学院
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