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2-aryl-3-methyl benzofuran-benzimidazole salt compound and preparation method thereof

A kind of salt compound, technology of benzimidazole, applied in the application field of anti-tumor

Inactive Publication Date: 2017-06-23
YUNNAN MINZU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Combining benzofuran with good biological activity with benzimidazole and its derivatives to form a novel structure of benzofuran-benzimidazole salt compounds, aiming to find new drugs with better pharmacological activity, currently at home and abroad There are few reports on these compounds

Method used

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  • 2-aryl-3-methyl benzofuran-benzimidazole salt compound and preparation method thereof
  • 2-aryl-3-methyl benzofuran-benzimidazole salt compound and preparation method thereof
  • 2-aryl-3-methyl benzofuran-benzimidazole salt compound and preparation method thereof

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preparation example Construction

[0019] The preparation method specifically includes:

[0020] A, the preparation of compound benzyl ether salicylaldehyde:

[0021] Using salicylaldehyde as raw material, synthesize benzyl ether salicylaldehyde with 4-substituted benzyl bromide in anhydrous DMF: dissolve salicylaldehyde, 4-bromobenzyl bromide or 4-trifluoromethyl benzyl bromide in anhydrous DMF , adding potassium carbonate, the dosage is salicylaldehyde in molar ratio: 4-substituted benzyl bromide: potassium carbonate = 1: 1: 2, the dosage of anhydrous DMF is 30 ml: 1g salicylaldehyde, stirred at 100°C for 10 After 1 hour, cool to room temperature, filter with suction, add ethyl acetate to dilute (50 ml: 1g substrate), wash with water (50 ml) and saturated brine (50 ml) respectively, and wash the organic phase with anhydrous MgSO 4 After drying, filtering, and concentrating the solvent under reduced pressure, perform silica gel column chromatography, using petroleum ether: ethyl acetate (30: 1) as the eluent,...

Embodiment 1

[0033] Preparation of compound 9: see the above preparation methods A, B, C, D, E, F.

[0034]

[0035] Compound 9: Molecular Formula C 31 h 24 Br 2 N 2 o 3 , yield 63%, white solid. IR ν max (cm -1): 3436,3329, 3137, 2921, 1680, 1606, 1446, 1248, 1178, 1120, 1025, 984, 833, 754,699 cm -1 . 1 H-NMR (300 MHz ,DMSO) δ: 9.79 (1H, s), 8.09-8.04 (3H, m), 7.94-7.70 (6H, m), 7.69-7.43 (3H, m), 7.42-7.39 (1H , t, J=4.5 Hz), 7.33-7.28 (1H, t , J=7.5 Hz), 7.17-7.14 (2H, d, J=8.7 Hz), 6.31 (2H, s), 6.24 (2H, s) , 3.88 (3H,s). 13 C-NMR (75 Hz, DMSO) Δ: 189.30, 164.13, 154.37, 153.54, 143.06, 132.28,132.10, 130.80, 130.28, 129.40, 129.64, 127.46.98, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126.72, 126. , 123.68, 123.45, 119.78, 114.26, 114.10, 113.69, 111.53, 108.10, 107.42, 55.77, 52.93, 41.73. 31 h 24 BrN 2 o 3 + [M-Br] + 551.0965, found: 551.0923.

Embodiment 2

[0037] Preparation of compound 10: see the above preparation methods A, B, C, D, E, F.

[0038]

[0039] Compound 10: Molecular Formula C 34 h 24 Br 2 N 2 o 2 , yield 80%, white solid. IR ν max (cm -1 ): Yield 80%, white solid, IR(KBr): 3428, 3321, 3126, 2917, 1686, 1615, 1564, 1446, 1264,1188, 1124, 1071, 1006, 822, 754, 696 cm -1 . 1 H-NMR (300 MHz, DMSO) δ: 9.84 (1H, s), 8.92 (1H, s), 8.22-8.01 (5H, m), 7.97-7.81 (5H, m), 7.75-7.65 (6H, m ),7.64-7.59 (1H, t, J=7.5 Hz), 7.43-7.32 (1H, m), 6.54 (2H, s), 6.28 (2H, s). 13 C-NMR (75 Hz, DMSO) Δ: 191.04, 154.39, 153.55, 143.09, 135.50, 132.30,131.97, 130.88, 130.01, 129.99, 129.33, 128.05,127.8.8.7.48, 127.7.7.7.7.7.7.7.7.7.8 , 125.68, 123.71, 123.27, 119.81,114.17, 113.73, 111.55, 107.43, 53.41, 41.79. HRMS (ESI-TOF) m / z: Calcd for C 34 h 24 BrN 2 o 2 + [M-Br] + 571.1016, found: 571.1054.

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Abstract

The invention discloses a series of 2-aryl-3-methyl benzofuran-benzimidazole salt compound with a structure general formula (such as formula I or II) and a preparation method thereof. The preparation method comprises the following steps: taking salicylic aldehyde as a raw material and synthesizing benzylide salicylic aldehyde with 4-substituted benzyl bromide in anhydrous DMF; then synthesizing 2-aryl-3-methyl benzofuran in phosphorus oxychloride and the anhydrous DMF; successively synthesizing 2-aryl-3-methanol benzofuran with sodium borohydride in methanol; finally firstly synthesizing methanesulfonate with methanesulfonyl chloride in dichloromethane, then synthesizing 2-aryl-3-methyl benzofuran-benzimidazole with benzimidazole or 5,6-dimethyl benzimidazole in methylbenzene and on the basis, synthesizing the 2-aryl-3-methyl benzofuran-benzimidazole salt compound with brominated alkanes in methylbenzene. The compound shows better antitumor cytotoxic activity.

Description

[0001] Technical field: [0002] The invention relates to a novel 2-aryl-3-methylbenzofuran-benzimidazolium salt compound and a preparation method thereof, as well as the anti-tumor application of a pharmaceutical composition in which the compound is an active ingredient. [0003] Background technique: [0004] In recent years, rational molecular hybridization between pharmacophore or active compounds, as a new strategy for drug discovery, has received great attention from synthetic and medicinal chemists. By hybridizing two pharmacophores with the same or different pharmacological activities, such a synthetic method can not only increase the affinity for a single target of a receptor that affects a certain disease, but also act on two or two receptors at the same time. The above targets have double or even multiple effects on the treatment of diseases. Many novel compounds designed through molecular hybridization exhibit diverse biological activities and are currently widely ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C07D403/06A61P35/00
CPCC07D405/06C07D403/06
Inventor 杨丽娟段坤元赵芳杜瑶杨云汉
Owner YUNNAN MINZU UNIV
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