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1-(3-indolyl)-1,2,3,4-tetrahydro-beta-carboline derivative and its prepn and use

A technology of indolyl and derivatives, applied in botany equipment and methods, chemicals for biological control, biocides, etc., can solve the problems of anti-tumor drugs that cannot meet the needs of treatment, chemotherapy failure, tumor cell growth, etc. question

Inactive Publication Date: 2007-08-22
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the tumor has the ability to metastasize in the early stage, about 50% of the patients with clinically diagnosed primary tumors have developed distant metastases. More than 90% are related to the multidrug resistance of tumor cells, and the anti-tumor drugs currently used in clinical practice are far from meeting the requirements of treatment

Method used

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  • 1-(3-indolyl)-1,2,3,4-tetrahydro-beta-carboline derivative and its prepn and use
  • 1-(3-indolyl)-1,2,3,4-tetrahydro-beta-carboline derivative and its prepn and use
  • 1-(3-indolyl)-1,2,3,4-tetrahydro-beta-carboline derivative and its prepn and use

Examples

Experimental program
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Effect test

Embodiment 1

[0091] Embodiment 1: synthetic compound 1,1-(3-indolyl)-2-benzoyl-1,2,3,4-tetrahydro-β-carboline 1) Preparation of indole-3-formaldehyde

[0092] Put 56ml of DMF into a 500ml three-neck flask, stir in an ice-salt bath, keep the temperature not exceeding 0°C, and add 17.4ml (0.186mol) of phosphorus oxychloride dropwise. Then slowly add 20 ml of DMF solution containing 20 g (0.171 mol) of indole dropwise, and finish dropping within 1 hour. After the dropwise addition, the temperature of the reaction solution was kept at 35° C. for 1.5 hours. Under cooling in an ice-water bath, add 80ml of ice water, then slowly add 200ml of aqueous solution containing 80g of sodium hydroxide (1 / 3 of the amount is slowly added first, and the rest is added at one time), heat and reflux for 15 minutes, cool and place in the refrigerator 4 hours. Suction filtration, the filter cake was washed with a large amount of water, after being drained, it was dried under an infrared lamp. 23.0 g of light y...

Embodiment 2

[0099] Example 2: Synthetic compound 2,1-(3-indolyl)-2-o-chlorobenzoyl-1,2,3,4-tetrahydro-β-carboline

[0100] 1-(3-indolyl)-1,2,3,4-tetrahydro-β-carboline reacts with o-chlorobenzoyl chloride, the synthesis process is the same as 1. Yield: 27.0%. 1 HNMR (CDCl 3 )δ (ppm): 2.76 (m, 1H, Carboline-C 4 -H), 3.12(m, 1H, Carboline-C 4 -H), 3.48(m, 2H, Carboline-C 3 -H), 6.88-7.75 (m, 14H, Ar-H), 8.09-8.33 (m, 2H, NH). MS (ESI) m / z (M-1) 424.1.

Embodiment 3

[0101] Example 3: Synthetic compound 3,1-(3-indolyl)-2-p-chlorobenzoyl-1,2,3,4-tetrahydro-β-carboline

[0102]1-(3-indolyl)-1,2,3,4-tetrahydro-β-carboline reacts with p-chlorobenzoyl chloride, the synthesis process is the same as 1. Yield: 60.8%. 1 HNMR (DMSO-d6) δ (ppm): 2.71-2.85 (m, 2H, Carboline-C 4 -H), 3.40(m, 1H, Carboline-C 3 -H), 3.55(m, 1H, Carboline-C 3 -H), 6.88(s, 1H, Carboline-C 1 -H), 6.95-7.03(m, 2H, Indole-C 6’ -H+Carboline-C 7 -H), 7.05-7.12(m, 2H, Indole-C 5’ -H+Carboline-C 6 -H), 7.20(s, 1H, Indole-C 2’ -H), 7.28(d, 1H, Indole-C 7’ -H, J=7.8Hz), 7.34-7.40 (m, 3H, Ar-H+Carboline-C 8 -H), 7.44-7.52(m, 3H, Ar-H+Carboline-C 5 -H), 7.63(d, 1H, Indole-C 4’ -H, J=7.8 Hz), 11.05-11.10 (m, 2H, NH). MS (ESI) m / z (M-1) 424.1.

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Abstract

The present invention belongs to the field of medicine synthesis technology, and is especially 1- (3-indolyl)-1, 2, 3, 4-tetrahydro-beta-carboline compounds and analogs in the general expression as shown and with substituted hydroxyl radical or acyl radical in the 2nd position, and their preparation process and medical application. Initial pharmacodynamic research of extracorporeal rice blast mold resisting experiment and extracorporeal antitumor experiment shows that these compounds has excellent antifungal activity and antitumor activity, so that they may be developed into antifungal medicine and antitumor medicine.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to 1-(3-indolyl)-1,2,3,4-tetrahydro-β-carboline derivatives, a preparation method and application. Specifically relate to a kind of 1-(3-indolyl)-1,2,3,4-tetrahydro-β-carboline derivatives substituted by various hydrocarbyl or acyl groups at the 2-position, its preparation method and its medical application Applications. Background technique [0002] The emergence of antibiotics has ushered in a new era of medical revolution. However, with the popularity and abuse of antibiotics around the world, both Gram-positive bacteria and negative bacteria have shown a trend of drug resistance. Among them, the problem of drug resistance of Gram-positive bacteria is particularly serious. serious. According to reports, some non-pathogenic bacteria have become conditional pathogens, such as Proteus, Pseudomonas aeruginosa, etc. Infections such as viruses and deep fungi still lack good prevention and...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61P31/10A61P35/00A01N43/90A01P3/00
Inventor 闻韧郑剑斌董肖椿
Owner FUDAN UNIV
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