Unlock instant, AI-driven research and patent intelligence for your innovation.

Trans-3-indolyl-4-pyrroldiazepinecycloheptane-2,5-pyrrolidine-2,5-diketone compound and preparation method thereof

A technology of diazepines and compounds, applied in the field of pharmaceutical chemical synthesis

Active Publication Date: 2014-05-28
四川阳光润禾药业有限公司
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But anticancer drugs can also inhibit the growth of normal cells while killing cancer cells, so most drugs have certain side effects

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Trans-3-indolyl-4-pyrroldiazepinecycloheptane-2,5-pyrrolidine-2,5-diketone compound and preparation method thereof
  • Trans-3-indolyl-4-pyrroldiazepinecycloheptane-2,5-pyrrolidine-2,5-diketone compound and preparation method thereof
  • Trans-3-indolyl-4-pyrroldiazepinecycloheptane-2,5-pyrrolidine-2,5-diketone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of embodiment 1 intermediate 2-(1H-indol-7-yl) acetonitrile

[0035]

[0036] Add 7-formylindole (14.8g, 100mmol) and dry tetrahydrofuran (300ml) to a dry three-necked flask, then add lithium cyanide (350mg, 10mmol) and diethyl cyanophosphate (19.7ml, 130mmol) in sequence ), and stirred overnight at room temperature. After the reaction was detected by TLC, tert-butanol (10.0 ml, 100 mmol) was added and stirred for 30 minutes. At room temperature, the mixture was slowly added dropwise into 0.1M samarium iodide tetrahydrofuran solution (3.0L, 300mmol). After the addition was complete, stirring was continued for 30 minutes. The mixture was evaporated to dryness under reduced pressure, diluted with 2 liters of ethyl acetate, and then transferred to a separatory funnel, washed with 1N dilute hydrochloric acid (500ml×3), saturated sodium bicarbonate (500ml×2) and saturated saline (500ml) washing. Dry over anhydrous magnesium sulfate, filter and spin dry...

Embodiment 2

[0038] Preparation of Embodiment 2 Intermediate 2-(1H-indol-7-yl)ethylamine

[0039]

[0040] 2-(1H-indol-7-yl)acetonitrile (8.5g, 53.8mmol), Raney nickel (8.5g) and ammonia (3.6g) methanol ( 300ml) solution. Hydrogen gas was introduced to keep the pressure at 340 kPa (50 psi), and the mixture was stirred overnight at room temperature. After the reaction was completed, the Raney nickel was removed by filtration, evaporated to dryness under reduced pressure, and the residual solution was diluted with ethyl acetate / water (1:1, 500ml), stirred for 15 minutes and then separated. The organic layer was washed with saturated brine (100ml×2), dried over anhydrous sodium sulfate, filtered, and spin-dried to give 2-(1H-indol-7-yl)ethylamine (8.1g, 94%) as light yellow oil. LCMS (M+H)=161. Preparation of Example 3 Intermediate 2-(1H-indol-7-yl) ethyl tert-butyl carbamate

Embodiment 3

[0040] 2-(1H-indol-7-yl)acetonitrile (8.5g, 53.8mmol), Raney nickel (8.5g) and ammonia (3.6g) methanol ( 300ml) solution. Hydrogen gas was introduced to keep the pressure at 340 kPa (50 psi), and the mixture was stirred overnight at room temperature. After the reaction was completed, the Raney nickel was removed by filtration, evaporated to dryness under reduced pressure, and the residual solution was diluted with ethyl acetate / water (1:1, 500ml), stirred for 15 minutes and then separated. The organic layer was washed with saturated brine (100ml×2), dried over anhydrous sodium sulfate, filtered, and spin-dried to give 2-(1H-indol-7-yl)ethylamine (8.1g, 94%) as light yellow oil. LCMS (M+H)=161. Preparation of Example 3 Intermediate 2-(1H-indol-7-yl) ethyl tert-butyl carbamate

[0041]

[0042] Under nitrogen protection, 2-(1H-indol-7-yl)ethylamine (8.4g, 52.5mmol), dry tetrahydrofuran (200ml) and triethylamine (13.4 g, 131.2mmol), under stirring, a mixture of di-tert-but...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to the field of chemical synthesis of medicaments, in particular to a trans-3-indolyl-4-pyrroldiazepinecycloheptane-2,5-pyrrolidine-2,5-diketone compound and a preparation method thereof. Research trails on the tumor suppression effect of tumor-bearing mice find that the compound has an obvious tumor suppression effect and can be applied to preparation of anti-tumor medicaments.

Description

technical field [0001] The present invention relates to the field of pharmaceutical chemical synthesis, in particular to a trans-3-indolyl-4-indolodiazepanyl-2,5-pyrrolidine-2,5-dione compound and its preparation method. Background technique [0002] Cancer is also called malignant neoplasm in medical terms, and cancer cells are defined as heterogeneous cells. At present, due to factors such as changes in people's environment and lifestyle, the morbidity and mortality of cancer continue to increase. In fact, tumors have gradually replaced cardiovascular and cerebrovascular diseases as the number one killer in the world, and the incidence of malignant tumors in my country is rising particularly rapidly. According to the survey, the prevalence of cancer in my country is increasing at a rate of 3%-5% per year, and there are more than 2.2 million new cancer cases every year, among which liver cancer, lung cancer, and gastric cancer are the three high incidences. [0003] Ther...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/06A61K31/551A61P35/00
Inventor 王颖闫革新张勇
Owner 四川阳光润禾药业有限公司