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4-alkyl-6-aryl-5-acetyl-1, 3-thiazine, and preparation method and application thereof

A technology of alkyl and thiazine, which is applied in the fields of drug combination, active ingredient of heterocyclic compounds, organic chemistry, etc., and can solve the problem of no research and development reports on anti-tumor activity

Inactive Publication Date: 2011-05-25
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 4-Alkyl-6-aryl-5-acetyl-2-amino-1,3-thiazine or 4-alkyl-6-aryl-5-acetyl-2-amido-1,3- There is no research and development report on the preparation of thiazide and its antitumor activity

Method used

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  • 4-alkyl-6-aryl-5-acetyl-1, 3-thiazine, and preparation method and application thereof
  • 4-alkyl-6-aryl-5-acetyl-1, 3-thiazine, and preparation method and application thereof
  • 4-alkyl-6-aryl-5-acetyl-1, 3-thiazine, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1 4-methyl-6-(2-methoxyphenyl)-5-acetyl-2-amino-1,3-thiazine and 4-methyl-6-(2-methoxybenzene base)-5-acetyl-2-acetylamino-1, the preparation of 3-thiazine

[0023] (1) Preparation of 4-methyl-6-(2-methoxyphenyl)-5-acetyl-2-amino-1,3-thiazine [0023]8.5mmol thiourea, 8.5mmol 3-( 2-methoxybenzylidene)-2,4-pentanedione, 1ml of concentrated hydrochloric acid, 45ml of ethanol, reflux and water separation reaction for 6.0h, 4-methyl-6-(2-methoxybenzene base)-5-acetyl-2-amino-1,3-thiazine, the yield is 18%, and the melting point is 188-190°C. 1 H NMR (400M Hz, CDCl 3 ), δ: 2.20 (s, 3H, COCH 3 ), 2.49 (s, 3H, CH 3 ), 3.91 (s, 3H, OCH 3 ), 5.59 (s, 1H, thiazine ring 6-H), 6.83-7.24 (m, 4H, benzene ring).

[0024] (2) Preparation of 4-methyl-6-(2-methoxyphenyl)-5-acetyl-2-acetylamino-1,3-thiazine

[0025] 1.0mmol 4-methyl-6-(2-methoxyphenyl)-5-acetyl-2-amino-1,3-thiazine, 1.0ml acetic anhydride, appropriate amount of DMAP, 5.0ml tetrahydrofuran, at 45~60 Stir at ℃...

Embodiment 2

[0026] Example 2 4-methyl-6-(2-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine and 4-methyl-6-(2-nitrophenyl) - Preparation of 5-acetyl-2-acetylamino-1,3-thiazine

[0027] (1) Preparation of 4-methyl-6-(2-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine

[0028] 11mmol of thiourea, 11mmmol of 3-(2-nitrobenzylidene)-2,4-pentanedione, 1ml of concentrated hydrochloric acid, 50ml of ethanol, reflux and water separation for 6.5h, and 4-methyl-6 -(2-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine, yield 47%, melting point 205-207°C.

[0029] (2) Preparation of 4-methyl-6-(2-nitrophenyl)-5-acetyl-2-acetylamino-1,3-thiazine

[0030] 2.0mmol 4-methyl-6-(2-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine, 2.0ml acetic anhydride, appropriate amount of DMAP, 5.0ml tetrahydrofuran, at 45~60℃ Stir for 0.6h, spin evaporate the solvent, add water, filter with suction and dry to obtain 4-methyl-6-(2-nitrophenyl)-5-acetyl-2-acetylamino-1,3-thiazine. The yield is 63%, and the melting point is 166-168°C. 1 H NMR ...

Embodiment 3

[0031] Example 3 4-methyl-6-(3-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine and 4-methyl-6-(3-nitrophenyl) - Preparation of 5-acetyl-2-acetylamino-1,3-thiazine

[0032] (1) Preparation of 4-methyl-6-(3-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine

[0033] 10mmol of thiourea, 10mmmol of 3-(3-nitrobenzylidene)-2,4-pentanedione, 1ml of concentrated hydrochloric acid, 50ml of ethanol, reflux and water separation for 8.0h, and 4-methyl-6 -(3-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine, yield 58%, melting point 177-178°C.

[0034] (2) Preparation of 4-methyl-6-(3-nitrophenyl)-5-acetyl-2-acetylamino-1,3-thiazine

[0035] 2.0mmol 4-methyl-6-(3-nitrophenyl)-5-acetyl-2-amino-1,3-thiazine, 2.0ml acetic anhydride, appropriate amount of DMAP, 5.0ml tetrahydrofuran, at 45~60℃ Stir for 1.1h, spin evaporate the solvent, add water, filter with suction and dry to obtain 4-methyl-6-(3-nitrophenyl)-5-acetyl-2-acetylamino-1,3-thiazine. The yield is 88%, and the melting point is 170-171°C. 1 H NMR (4...

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Abstract

The invention discloses a compound shown as a chemical structural formula I or II and pharmaceutically acceptable salt thereof. The compound shown as the chemical structural formula I or II has a following preparation method that 2-toluenyl-1-alkyl-1, 3-butanedione and thiourea take reaction under stirring in organic solvents at 55 DEG C to 80 DEG C under the catalysis of HY acid to obtain 4-alkyl-6-aryl-5-acetyl-2-amino-1, 3-thiazine salt (I.HY), the 4-alkyl-6-aryl-5-acetyl-2-amino-1, 3-thiazine salt is neutralized by alkali to obtain the compound as shown as the formula I, and the compound shown as the formula I is subject to acidylation to obtain the compound shown as the formula II. The compound shown as the formula I or the formula II has good inhibitory activity on human cervical carcinoma cells (Hela cells), human hepatocarcinoma cells (Bel 7402 cells) and human lung adenocarcinoma cells (A549 cells) and can be used for preparing anti-tumor medicine.

Description

technical field [0001] The present invention relates to a new class of compound and its preparation method and application, specifically 4-alkyl-6-aryl-5-acetyl-2-amido-1,3-thiazine and its preparation method and application. Background technique [0002] Among China's 1.3 billion people, one million people die of cancer every year, about 2 million need treatment, and about 1.3 million die. Cancer has become a major killer of human beings. [0003] Michael et al. described 2-aminothiazole breast cancer drugs (Bioorg & Med.Chem.2004, 12, 1029); Chinese patent (CN 200910226728.5) described 4-tert-butyl-5-(1,2,4-tri Antitumor activity of azole-1-yl)-2-benziminothiazole; Hu Aixi et al. described the antitumor activity of 5-benzyl-4-tert-butyl-2-benziminothiazole [CN 200910226774.5, CN 101781269] . Hu Aixi et al. described the preparation of 4-(benzofuran-5-yl)-2-benziminothiazole and its antitumor activity [CN 201010533786.5]. [0004] 4-Alkyl-6-aryl-5-acetyl-2-amino-1,3-thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/04A61K31/54A61P35/00
Inventor 胡艾希夏曙李婉叶姣彭俊梅谭卫清向建南
Owner HUNAN UNIV
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