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N-alkyl substituted indole-imidazolium salt compounds, and preparation method thereof

A salt compound and compound technology, applied in organic chemistry, drug combination, pharmaceutical formulation, etc.

Inactive Publication Date: 2017-07-04
YUNNAN MINZU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Combine indole with imidazole and its derivatives with good biological activity to form indole-monoimidazole salt compounds with novel structure, aiming to find new drugs with good pharmacological activity. At present, there are few such compounds at home and abroad. There are reports

Method used

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  • N-alkyl substituted indole-imidazolium salt compounds, and preparation method thereof
  • N-alkyl substituted indole-imidazolium salt compounds, and preparation method thereof
  • N-alkyl substituted indole-imidazolium salt compounds, and preparation method thereof

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preparation example Construction

[0021] The preparation method specifically includes:

[0022] A, the preparation of compound N-alkyl substituted indole:

[0023] Using indole as raw material, synthesize N-alkyl substituted indole with dibromoalkane in anhydrous DMF solvent: dissolve indole in anhydrous DMF, add sodium hydroxide solid at 0 ℃, the amount is molar ratio For indole: sodium hydroxide = 1: 2, the dosage of anhydrous DMF is 20 ml: 1g indole, stir for 5 minutes, then add dibromoalkane (1,3-dibromopropane, 1,4- Dibromobutane or 1,5-dibromopentane) in anhydrous DMF, the molar ratio is dibromoalkane:indole=3:1, the amount of anhydrous DMF is 5 ml : 1 ml dibromoalkane , after stirring and reacting at room temperature for 5 hours, dilute with ethyl acetate (50 ml: 1g substrate), wash with water (50 ml) and saturated brine (50 ml) respectively, and wash the organic phase with anhydrous Na 2 SO 4 After drying, filtering, and concentrating the solvent under reduced pressure, silica gel column chromatogra...

Embodiment 1

[0029] Preparation of Compound 5: See Preparation Methods A, B, and C above.

[0030]

[0031] Compound 5: Formula C 27 h 27 Br 2 N 3 , yield 69%. White solid, m.p. 108-109 o C. IR ν max (cm -1 ): 3446, 3129, 2361, 2052, 1611, 1562, 1445, 1384, 1312, 1268, 1222, 1129, 1069, 1024, 957, 860, 743, 616, 563, 428. 1 H NMR (400 MHz, DMSO): δ9.72 (1H, s), 7.75 (2H, s), 7.68 (1H, s), 7.55-7.53 (1H, d, J =7.37 Hz),7.49-7.47 (1H, d, J =7.69Hz),7.41-7.35(3H,m),7.29-7.27(1H,d, J =6.73Hz), 7.12-7.09 (1H, t, J = 14.11 Hz), 7.03-7.00 (1H, t, J = 13.47 Hz), 6.43 (1H, s), 5.71 (2H, s), 4.52 (2H, s), 4.36 (2H, s), 2.43 (2H, s), 2.35 (6H, s). 13 C NMR(100 MHz, DSMO): δ 141.82, 136.61, 136.54, 135.57, 133.26, 132.87, 130.92,130.37, 129.64, 129.56, 128.58, 128.47, 128.30, 128.16, 122.91, 121.14,120.55, 119.14, 113.34, 113.17, 109.87, 100.89, 50.20, 44.66, 42.80, 29.22, 20.08, 20.01.

Embodiment 2

[0033] Preparation of Compound 6: See Preparation Methods A, B, and C above.

[0034]

[0035] Compound 6: Molecular Formula C 27 h 28 BrN 3 , Yield 63%. White solid, m.p.164-165 o C.IRν max (cm -1 ):3448, 3128, 2320, 2051, 1644, 1561, 1456, 1354, 1262, 1128, 1069, 994, 955,861, 743, 614, 541. 1 HNMR(400MHz,DMSO):δ9.79(1H,s),9.48(1H,s),7.71 (1H,s),7.67 (1H,s), 7.55-7.53 (1H,d, J = 7.66 Hz), 7.48-7.46 (1H, d, J = 8.06 Hz),7.41-7.40 (1H, d, J = 3.07 Hz), 7.39 (1H, s), 7.37 (1H, s), 7.21 (1H, s),7.19 (1H, s), 7.13-7.09 (1H, m), 7.04-7.00 (1H, m) , 6.43-6.42 (1H, d, J =3.04 Hz), 5.59 (2H, s), 4.48-4.44 (2H, t, J= 14.76 Hz), 4.38-4.34 (2H, t, J = 13.75 Hz), 2.47-2.43 (2H, t, J = 14.29 Hz), 2.35 (3H, s), 2.34 (3H, s),2.27 (3H, s). 13 C NMR (100 MHz, DSMO): δ 141.11, 138.04, 136.28, 135.53,131.07, 129.63, 129.44, 129.29, 128.45, 128.19, 128.13, 121.07, 120.49,119.07, 113.20, 113.08, 109.75, 100.87, 49.45, 44.51, 42.75, 29.01, 20.69, 19.99, 19.92.

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Abstract

The invention discloses a series of N-alkyl substituted indole-imidazolium salt compounds having a structural formula (represented b figure I), and a preparation method thereof. The preparation method comprises the following steps: synthesizing N-alkyl substituted indole from indole used as a raw material and dibromoalkane in an anhydrous DMF solvent, carrying out a heating reaction on the N-alkyl substituted indole and 5,6-dimethylbenzimidazole in a toluene solvent to synthesize N-alkyl substituted indole-imidazole, and carrying out a refluxing reaction on the N-alkyl substituted indole-imidazole and bromoalkane in the toluene solvent to synthesize the N-alkyl substituted indole-imidazolium salt compounds. The compounds have good anti-tumor cytotoxicity activity.

Description

[0001] Technical field: [0002] The invention relates to a novel N-alkyl substituted indole-imidazolium 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 use...

Claims

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Application Information

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IPC IPC(8): C07D403/06A61K31/4184A61P35/00
CPCC07D403/06
Inventor 杨丽娟陈兴常清李燕华施义民苟玉鹏
Owner YUNNAN MINZU UNIV
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