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Isomannide-bis-benzimidazole salt compounds and preparation method thereof

A technology of isomannitol and bisbenzimidazole, which is applied in the field of isomannitol-bisbenzimidazole salt compounds and their preparation, and can solve the problems of high drug requirements

Inactive Publication Date: 2017-05-10
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, molecular targeted therapy has high requirements for the required drugs and requires strong targeting of tumor cells. Many chemical drugs cannot meet this condition very well. Therefore, it is imminent to develop new anti-tumor chemical drugs.

Method used

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  • Isomannide-bis-benzimidazole salt compounds and preparation method thereof
  • Isomannide-bis-benzimidazole salt compounds and preparation method thereof
  • Isomannide-bis-benzimidazole salt compounds and preparation method thereof

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preparation example Construction

[0016] The preparation method specifically includes:

[0017] A, the preparation of compound isomannitol p-toluenesulfonate:

[0018] Using isomannitol as raw material, synthesize isomannitol p-toluenesulfonate with p-toluenesulfonyl chloride in dichloromethane: add isomannitol to dichloromethane to dissolve it completely, then add anhydrous pyridine, 0 Add p-toluenesulfonyl chloride dropwise under the condition of ℃, the dosage is isomannitol: anhydrous pyridine: p-toluenesulfonyl chloride = 1: 4.0: 2.5, the dosage of dichloromethane is 25-50 ml: 1g isomannitol Mannitol, after all the addition is complete and completely dissolved, rise to room temperature, stir the reaction for 12 h until the thin layer chromatography shows that the raw material is completely reacted, add dichloromethane to dilute (50 ml: g substrate), and then use 1N hydrochloric acid ( 50 ml) and saturated brine (50 ml), the organic phase was washed with anhydrous NaSO 4 After drying, filtering, and conce...

Embodiment 1

[0024] Preparation of Compound 4a: See Preparation Methods A, B, and C above.

[0025]

[0026] Compound 4a: Formula C 34 h 30 Br 4 N 4 o 2 ,yield 67%. White solid powder, mp 151-153 o c. 1 H NMR (300 MHz, DMSO-d 6 ): δ 10.12 (2H, s), 8.27 (1H, s), 8.24 (1H, s), 7.83-7.66(10H, m), 7.39-7.32 (6H, m), 5.91-5.89 (4H, m) , 5.80 (2H, t, J = 3.9 Hz),5.45 (2H, s), 4.64 (4H, d, J = 3.6 Hz). 13 C NMR (75 MHz, DMSO-d 6 ): δ 143.83,142.26, 133.31, 133.15, 132.52, 131.13, 131.05, 130.91, 130.85, 130.73,129.95, 128.46, 128.31, 127.26, 127.12, 123.03, 122.56, 114.12, 114.04,113.88, 86.43, 70.82, 62.53, 50.53 . HRMS (ESI-TOF) m / z Calcd for C 34 h 29 Br 2 N 4 o 2 + [M-2Br-H] + 683.0651, found 683.0647.

Embodiment 2

[0028] Preparation of Compound 4b: See Preparation Methods A, B, and C above.

[0029]

[0030] Compound 4b: Formula C 36 h 36 Br 2 N 4 o 2 , Yield 83%. White solid powder, mp 263-264 o c. 1 H NMR (300 MHz, DMSO-d 6 ): δ 10.28-10.22 (2H, m), 8.22 (1H, s), 8.20 (1H, s), 7.93-7.91 (2H, m), 7.75-7.62 (4H, m), 7.48-7.47 (4H, m), 7.21-7.19 (4H, m), 5.78(6H, s), 5.48 (1H, s), 5.46 (1H, s), 4.65 (4H, s), 2.28 (6H, d, J = 4.8 Hz ). 13 C NMR (75 MHz, DMSO-d 6): δ 142.40, 141.25, 138.17, 138.06, 131.02, 130.90,130.77, 130.60, 129.50, 129.35, 128.31, 126.96, 126.70, 126.12, 114.41,114.13, 113.97, 86.37, 70.80, 62.48, 49.89, 49.80, 20.68. HRMS (ESI-TOF) m / zCalcd for C 36 h 35 N 4 o 2 + [M-2Br-H] + 555.2754, found 555.2757.

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Abstract

The invention discloses a series of isomannide-bis-benzimidazole salt compounds having a structural general formula (as in figure 1) and a preparation method thereof; isomannide, as a raw material, and 4-toluene sulfonyl chloride are converted into isomannide p-toluenesulfonate under dichloromethane and anhydrous pyridine, the isomannide p-toluenesulfonate and benzimidazole or 5,6-dimethylbenzimidazole are subjected to thermal reaction in anhydrous DMF (dimethylformamide) solvent to synthesize isomannide-bis-benzimidazole, and on such basis, the isomannide-bis-benzimidazole and alkyl bromide are subjected to reflux reaction in acetonitrile solvent to synthesize isomannide-bis-benzimidazole salt compounds. Results of in-vitro antitumor active cytotoxicity test indicate that part of the compounds have good cytotoxicity.

Description

technical field [0001] The invention relates to a novel isomannitol-bisbenzimidazole salt compound and a preparation method thereof, and the application of a pharmaceutical composition with the compound as an active ingredient in antitumor. Background technique [0002] In the field of anticancer drug research, more than 60% of drugs are derived from natural products. Searching for physiologically active compounds from natural products, designing and synthesizing quasi-natural product libraries based on their pharmacophore information, screening and discovering high-efficiency, high-selectivity, and low-toxicity lead compounds for clinical drug research, is the key to obtaining drug candidate molecules effective way. The traditional treatment methods for malignant tumors mainly include chemotherapy, radiotherapy and surgery. Among them, the cycle of radiotherapy is long, the cost is expensive, and it will cause various complications in the human body, which has a great adv...

Claims

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Application Information

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IPC IPC(8): C07D493/04A61K31/4184A61P35/00
CPCC07D493/04
Inventor 杨丽娟朱亮李燕华常清荀玉鹏杨云汉
Owner YUNNAN MINZU UNIV
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