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4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent

A technology of benzyliminothiazole and benzofuran is applied in 4-(benzofuran-5-yl)-2-benzyliminothiazole and its application field as an antitumor drug, which can solve the problem of no research on antitumor activity. and development reports

Inactive Publication Date: 2011-04-13
HUNAN UNIV
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Problems solved by technology

There is no research and development report on the preparation and antitumor activity of 4-(benzofuran-5-yl)-2-benziminothiazole

Method used

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  • 4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent
  • 4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent
  • 4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent

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Experimental program
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Embodiment 14

[0023]

[0024] (1) Preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone

[0025] 0.02mol 1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, 80ml ethanol, stirring and reflux, add 0.04mol copper bromide in batches , reacted for about 2.0h, filtered the reaction solution while it was hot, distilled and recovered the solvent, dissolved ethyl acetate, washed with dilute acid, filtered, washed the filtrate with water, separated, dried, and recrystallized from ethanol to obtain 2-bromo-1-(7-methyl Oxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, yield 50.0%, melting point 90-91°C.

[0026] 2) Preparation of 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole

[0027] 0.012mol 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone, 0.012mol thiourea, 60ml ethanol, heating and stirring , reacted for about 1.0h, the reaction solution was cooled to precipitate a solid, filtered, and the filter cake...

Embodiment 2

[0031]

[0032]According to the method of Example 1, 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole reacts with 4-fluorobenzaldehyde 1.5h; 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(4-fluorobenzimino)thiazole was obtained; yield 53.7%, melting point 148~150℃; 1 H NMR (CDCl 3 , 400MHz), δ: 1.55(s, 6H, 2×CH 3 ), 3.08 (s, 2H, CH 2 ), 3.96 (s, 3H, CH 3 ), 7.17~7.22 (m, 3H, C 6 h 4 2,6-H, thiazole ring 5-H), 7.35, 7.37 (2×s, 2H, C 6 h 2 ), 8.00~8.04 (m, 2H, C 6 h 4 3,5-H), 9.03 (s, 1H, N=CH).

Embodiment 34

[0034]

[0035] According to the method of Example 1, 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole and 4-dimethylaminobenzene Formaldehyde reaction for 9.0h; 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(4-dimethylaminobenzimino) was obtained Thiazole; yield 72.1%, melting point 166-168°C; 1 H NMR (CDCl 3 , 400MHz), δ: 1.54(s, 6H, 2×CH 3 ), 3.07 (s, 2H, CH 2 ), 3.09(s, 6H, 2×CH 3 ), 3.95 (s, 3H, CH 3 ), 6.73 (d, J=8.8Hz, 2H, C 6 h 4 3,5-H), 7.09 (s, 1H, thiazole ring 5-H), 7.35, 7.41 (2×s, 2H, C 6 h 2 ), 7.88 (d, J=8.8Hz, 2H, C 6 h 4 2,6-H), 8.81 (s, 1H, N=CH).

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Abstract

The invention discloses 4-(benzofuran-5-yl)-2-benzal aminothiazole as shown in a chemical structural formula I. The preparation method of the 4-(benzofuran-5-yl)-2-benzal aminothiazole is as follows: 1-(7-hydroxy / alkoxy-2,2-dimethyl-2,3-dihydro-benzofuran-5-yl) butanone is subject to bromination and reacts with thiourea to obtain 4-(7-hydroxy / alkoxy-2,2-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-aminothiazole which reacts with aromatic aldehyde to prepare the 4-(benzofuran-5-yl)-2-benzal aminothiazole. The 4-(benzofuran-5-yl)-2-benzal aminothiazole has good activity inhabiting activity on Hela cells, human liver cancer cells (Bel 7402 cells) and lung carcinoma cells (A549 cells) and can be used for preparing the antineoplastic agent.

Description

technical field [0001] The present invention relates to a new class of compound and its preparation method and application, specifically 4-(benzofuran-5-yl)-2-benziminothiazole, its preparation method and its application as an antitumor drug. Background technique [0002] Shao Ling et al. described 4-aryl-5-triazolylthiazole-2-imine compounds, and the results of biological activity assays showed that some compounds had bactericidal activity against P. ). Michael etc. have described 2-aminothiazole class breast cancer drug (Bioorg&Med.Chem.2004,12,1029); Acta Sinica, 2006, 41:727). Lin et al. described that Schiff bases have selective inhibitory effect on COX-2 (Bioorg & Med Chem, 2008, 16(5):2697). He Daohang et al. described the synthesis and bactericidal activity of 4-aryl-2-(2-hydroxybenzimino)thiazole [Journal of South China University of Technology, Natural Science Edition, 2008, (3): 60]; Chinese patent (CN 101602761, CN 200910226728.5) described the bactericidal a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A61K31/427A61P35/00
Inventor 胡艾希沈芳夏曙李婉向建南
Owner HUNAN UNIV
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