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Beta-carboline alkaloid, their preparation method and use

A technology of alkaloids and carbolines, which is applied in the treatment and prevention of AIDS. In the field of β-carboline alkaloids, it can solve the problems of no anti-HIV-1 activity of β-carboline alkaloids, and achieve good anti-HIV- 1 The effect of activity and small side effects

Inactive Publication Date: 2007-05-30
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] So far, there is no report in the prior art that the β-carboline alkaloid containing the compound of formula (I) has anti-HIV-1 activity, and there is no report on the compound as an active ingredient in the treatment of AIDS

Method used

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  • Beta-carboline alkaloid, their preparation method and use
  • Beta-carboline alkaloid, their preparation method and use
  • Beta-carboline alkaloid, their preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: Preparation 1-(5'-hydroxymethyl-2-furan)-β-carboline-3-formamide (compound 1)

[0052] Step A: Synthesis of L-Tryptophan Methyl Ester

[0053] Add 200mL dry methanol to 10mmol L-tryptophan, cool to below -10°C under magnetic stirring, slowly add 10mL thionyl chloride, then allow to rise to room temperature naturally, and then heat to reflux for 3h. Spin off excess methanol and thionyl chloride under reduced pressure, then add an appropriate amount of water to dissolve, adjust the pH value to 9-10, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and obtain a white Solid 2.13g, Yield: 98%, m.p.87-90℃.C 12 h 14 N 2 o 2 .EI-MS m / z: 218(15%), 159(10%), 130(100%), 77(13%). 1 H NMR (500MHz, CDCl 3 )δ (ppm): 8.27 (1H, s, br), 7.61 (1H, d, J = 7.8Hz), 7.35 (1H, d, J = 8.0Hz), 7.19 (1H, t, J = 7.4Hz) , 7.12(1H, t, J=7.4Hz), 7.05(1H, s), 3.83(1H, m), 3.71(3H, s), 3.28(1H, ...

Embodiment 2

[0058] Embodiment 2: Preparation of N-methyl-1-(5'-hydroxymethyl-2-furan)-β-carboline-3-formamide (compound 2)

[0059] Add 20 mL of methanol to 1 mmol of 1-(5'-acetoxymethyl-2-furan)-β-carboline-3-carboxylate, and add 4 mL of methylamine (33% methylamine in ethanol) under magnetic stirring , heated to 50°C, TLC showed that the raw material disappeared, the solvent was evaporated under reduced pressure, and column chromatography gave 193.2 mg of a yellow solid, Yield: 61%, mp241-314°C, C 18 h 15 N 3 o 3 .FAB + -MS m / z: 322(M+1). 1 H NMR (500MHz, DMSO-d 6 )δ (ppm): 11.52 (1H, s), 8.72 (1H, s), 8.39 (1H, d, J = 8.0Hz), 7.82 (1H, d, J = 8.0Hz), 7.68 (1H, d, J = 2.7Hz), 7.61 (2H, t, J = 8.5Hz), 7.31 (1H, t, J = 7, 5Hz), 6.62 (1H, d, J = 3.0Hz), 4.68 (2H, s), 2.90(3H,s). 13 C NMR (100MHz, DMSO-d 6 )δ (ppm): 164.9, 157.2, 151.7, 141.4, 139.6, 131.4, 130.2, 128.7, 128.6, 122.0, 121.0, 120.2, 112.7, 112.2, 111.0, 109.1, 55.9.

Embodiment 3

[0060] Example 3 Preparation of 1-(2-thiophene)-β-carboline-3-formamide (compound 3)

[0061] Step A: Synthesis of methyl 1-(2-thiophene)-β-carboline-3-carboxylate

[0062] Using 2-thiophene aldehyde and L-tryptophan methyl ester as raw materials, the operation is similar to step B of Example 1 to obtain 2.61 g of light yellow solid, Yield: 85%, mp151-154 °C, C 17 h 12 N 2 o 2 S.FAB + -MS m / z: 309(M+1). 1 HNMR (400MHz, CDCl 3 )δ (ppm): 8.75 (1H, s), 8.15 (1H, d, J = 8.0Hz), 7.82 (1H, d, J = 8.0Hz), 7.58 (2H, m), 7.47 (1H, d, J=4.0Hz), 7.33(1H, m), 7.16(1H, d, J=4.0Hz), 4.05(3H, s). 13 CNMR (100MHz, CDCl 3 )δ (ppm) 166.6, 141.6, 140.9, 136.9, 133.6, 130.0, 128.7, 127.8, 127.7, 127.6, 126.0, 121.6, 121.4, 120.8, 116.5, 112.2, 52.5.

[0063] Step B: Synthesis of 1-(2-thiophene)-β-carboline-3-carboxamide

[0064] Using methyl 1-(2-thiophene)-β-carboline-3-carboxylate as raw material, the operation was similar to Step C of Example 1 to obtain 205.4 mg of yellow solid, Yie...

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Abstract

The invention discloses a beta-carboline alkaloid and making method in the medicinical synthetic domain, which provides drug composition and application to treat and prevent AIDS with compound as formula I.

Description

Technical field: [0001] The invention belongs to the field of drug synthesis, and in particular relates to a beta-carboline alkaloid, its preparation method and its application in treating and preventing AIDS. Background technique: [0002] AIDS, also known as acquired immunodeficiency syndrome (Acquired Immunodeficiency Syndrome, AIDS), is an infectious disease caused by human immunodeficiency virus (Human Immunodeficiency Virus, HIV) infection, characterized by severe damage to the systemic immune system. The main clinical features of AIDS are the occurrence of opportunistic infections and tumors. Since it was first discovered in 1981, HIV has spread around the world at an alarming rate. The report "The Latest AIDS Epidemic Situation in 2006" pointed out that the number of people infected with AIDS in the world reached 42 million in 2006, of which 5 million were newly infected and 3 million died. [0003] Since there is no fundamental breakthrough in vaccine development,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P31/18C07D209/00C07D213/00C07D333/00
Inventor 刘吉开郑永唐汤建国王云华董泽军王睿睿王飞杨柳萌
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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