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Antitumor drug and preparation method and application thereof

An anti-tumor drug and drug technology, applied in anti-tumor drugs, drug combinations, organic chemistry and other directions, can solve the problems of poor targeting, complex structure, difficult synthesis, etc., to reduce production costs, the preparation method is simple and easy to operate, Achieve the effect of industrial production

Inactive Publication Date: 2019-04-05
熊磊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Common tubulin inhibitors are colchicine and its analogs, podophyllotoxin and its analogs, camptothecin, cyclolignan, vinblastine and its analogs, etc. The above inhibitors have complex structures and are difficult to synthesize , and poor targeting

Method used

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  • Antitumor drug and preparation method and application thereof
  • Antitumor drug and preparation method and application thereof
  • Antitumor drug and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] preparation

[0037] (1) Take 3-iodo-o-diamine (10mmol), N-tert-butoxycarbonyl-5-indole carboxaldehyde (11mmol), formic acid (12mmol), add to 20mL methanol, stir at 60°C for 5 hours to obtain Reaction solution: Add saturated aqueous sodium chloride solution and dichloromethane to the reaction solution for extraction, concentrate the organic phase and pass through column purification, collect the purified solution and distill under reduced pressure to obtain 4.0g (8.7mmol) N-tert-butoxycarbonyl-2 -(Acetamidomethyl)-3-bromopyrrole, the yield is 87%.

[0038] The hydrogen spectrum is as follows: 1 H NMR (400MHz, DMSO-d6) δ (ppm) = 1.63 (s, 9H), 5.85 (s, 1H), 6.38 (d, 1H), 6.99 (t, 1H), 7.46 (d, 1H), 7.59 (d,1H),7.65(d,1H),8.01(d,1H),8.15(d,1H),8.25(s,1H).

Embodiment 2

[0040] preparation

[0041] (1) take (5mmol), 4-trifluoromethylphenylboronic acid (5.5mmol), palladium acetate (0.1mmol), potassium acetate (6mmol), add 5mL dioxane and 5mL water, stir at 80°C for 10 hours to obtain the reaction liquid; the reaction solution was passed through diatomaceous earth, and the filtrate was collected; saturated aqueous sodium chloride solution and dichloromethane were added to the filtrate for extraction, and after the organic phase was concentrated, the column was purified, and the purified solution was distilled under reduced pressure to obtain 2.09g (4.4mmol) The yield was 88%.

[0042] The hydrogen spectrum is as follows: 1 H NMR (400MHz, DMSO-d6) δ (ppm) = 1 H NMR (400MHz, DMSO-d6) δ (ppm) = 1.63 (s, 9H), 5.87 (s, 1H), 6.56 (d, 1H), 7.35 (dd, 2H), 7.40 (d, 1H), 7.59 (d,1H), 7.65(d,1H), 7.69(dd,2H), 8.01(d,1H), 8.15(d,1H), 8.20(s,1H).

[0043] The inventor's initial synthetic route is (1) reacting 3-iodo o-phenylenediamine with 5-indole...

Embodiment 3

[0045] preparation That is, compound D shown in formula II:

[0046] (1) take (2mmol), was added to the hydrochloric acid-dioxane solution, stirred at 25°C for 3 hours to obtain a reaction solution; the reaction solution was distilled under reduced pressure to obtain 716mg (1.9mmol) The yield is 95%.

[0047] The hydrogen spectrum is as follows: 1 H NMR (400MHz, DMSO-d6) δ (ppm) = 5.85 (s, 1H), 6.53 (d, 1H), 7.38 (dd, 2H), 7.43 (d, 1H), 7.56 (d, 1H), 7.61 (d,1H), 7.68(dd,2H), 8.03(d,1H), 8.12(d,1H), 8.17(s,1H).

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Abstract

The invention provides an antitumor drug and a preparation method and application thereof. The antitumor drug has the structure as shown as the chemical compound D in the formula I, can effectively inhibit growth of tumor cells and increase weight of mice. Besides, effect of the drug in high dose is better than that of the drug in middle dose, and the effect of the drug in middle dose is better than that of the drug in low dose, in other words, the antitumor drug has concentration dependence. Further, the preparation method of the antitumor drug is simple and easy to operate and can effectively reduce production cost to realize industrialized production of the antitumor drug.

Description

technical field [0001] The field of the invention belongs to the field of medicine, and in particular relates to an antitumor medicine and its preparation method and application. Background technique [0002] At present, malignant tumors have become the number one killer of human beings, seriously endangering human health. According to the data of the World Health Organization, there are 10 million tumors in the world every year, and about 7 million people die. Tumors are generally divided into two categories, benign and malignant. The atypia of benign tumor cells is not obvious and is generally similar to its source tissue. Malignant tumors often have obvious atypia. [0003] In recent years, a new method has appeared in the treatment of malignant tumors, which is the natural therapy of negative air ions. A large number of clinical experiments have confirmed that air negative ion physiotherapy has a significant effect on cancer, and it is another new method in addition t...

Claims

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Application Information

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IPC IPC(8): C07D403/04A61P35/00
CPCA61P35/00C07D403/04
Inventor 熊磊刘晓菊王庆丰
Owner 熊磊
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