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Coffee acyl naphthalene sulfonamides compound and method for preparing the same and anti HIV conformity enzyme action

A technology of naphthalenesulfonamide and caffeamide, which is applied in the field of caffeoylnaphthalenesulfonamide compounds and their preparation, and achieves the effects of simple preparation method, favorable industrial production and high yield

Inactive Publication Date: 2004-03-17
QINGDAO HUANGHAI PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, caffeoyl and naphthalenesulfonyl are connected through an intermediate chain to design and synthesize a series of caffeoylnaphthalenesulfonamide compounds to enhance the inhibitory effect on HIV integrase.

Method used

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  • Coffee acyl naphthalene sulfonamides compound and method for preparing the same and anti HIV conformity enzyme action
  • Coffee acyl naphthalene sulfonamides compound and method for preparing the same and anti HIV conformity enzyme action
  • Coffee acyl naphthalene sulfonamides compound and method for preparing the same and anti HIV conformity enzyme action

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of 5-(N-phenylamino)-sulfonyl-1-naphthylamine (III)

[0028] Add 3 mL (45 mmol) of chlorosulfonic acid to sodium 5-(acetylamino)-1-naphthalenesulfonate (0.55 g, 2 mmol), stir and react at room temperature for 3 hours, slowly add the reactant dropwise to 40 mL of ice water, and stir , filtered the precipitate, dried to obtain a purple solid, added 3 mmol of aniline, reacted at room temperature for 3 hours, added 40 mL of water, adjusted the pH to 6 with dilute hydrochloric acid, precipitated, filtered, and recrystallized with ethanol to obtain brown crystals. Add this brown crystal (1.57mmol) to a mixed solution of 5mol / L sodium hydroxide (5mL) and methanol (3mL), stir and react at 70°C overnight, cool to room temperature, adjust the pH to 6 with 1mol / L hydrochloric acid, and precipitate out , filtered, drained, and recrystallized from ethanol / water to obtain 5-(N-phenylamino)-sulfonyl-1-naphthylamine, yellow crystals, yield 72%, mp: 170~172°C, R ...

Embodiment 2

[0039] Example 2. Preparation of N-[[5-[(N-phenyl)-amino]-sulfonyl]-1-naphthyl]-3,4-diacetylcaffeamide (II)

[0040] Dissolve 5-(N-phenylamino)-sulfonyl-1-naphthylamine (0.72mmol) in 5mL of acetone, add 5mL of 3,4-diacetylcaffeoyl chloride (0.25g, 0.82mmol) in acetone, and mix well , add 1 mL of pyridine, stir at room temperature for 40 hours, distill off the solvent under reduced pressure, add water and stir, there is precipitation, ethanol / water recrystallization, N-[[5-[(N-phenyl)-amino]-sulfonyl] -1-naphthyl]-3,4-diacetyl caffeamide, yield 63%, mp: 206~208 ℃, Rf=0.4 (ethyl acetate / petroleum ether 1:1); IR (KBr, cm -1 ): 3314, 3070, 1763, 1738, 1658, 1597, 1531, 1497, 1216, 1153, 906~693; 1 H-NMR (DMSO): 10.74(s, 1H), 10.34(s, 1H) 8.61(d, 1H, J=8.6Hz), 8.39(d, 1H, J=8.5Hz), 8.26(d, 1H, J=7.2Hz), 7.97(t, 1H, J=6.9Hz), 7.76(t, 1H, J=8.2Hz), 7.68~7.59(m, 4H), 737(d, 1H, J=8.2Hz) , 7.17~7.02 (m, 5H), 6.93 (t, 1H, J=7.4Hz), 2.31 (s, 6H). IC 50 >100ug / ml. Made by the same m...

Embodiment 3

[0050] Example 3. Preparation of N-[[5-[(N-phenyl)-amino]-sulfonyl]-1-naphthyl]-caffeamide (I)

[0051] Add N-[[5-[(N-phenyl)-amino]-sulfonyl]-1-naphthyl]-3,4-diacetylcaffeamide (2.0mmol) with methanol (2mL), tetrahydrofuran (2mL ) and concentrated hydrochloric acid (1mL), stirred and reacted at 60°C for 0.5 hours, cooled to room temperature, added distilled water (20mL), extracted with ethyl acetate (20mL×2), washed with saturated brine, dried over magnesium sulfate, and reduced Evaporate under pressure to remove solvent, recrystallize petroleum ether / ethyl acetate to obtain N-[[5-[(N-phenyl)-amino]-sulfonyl]-1-naphthyl]-caffeamide, yield 75% , mp: 256~258°C, Rf=0.5 (ethyl acetate / petroleum ether 2:1); IR (KBr, cm -1 ): 3346, 3250, 3037, 1664, 1598, 1516, 1493, 1284, 1147, 927~687; 1 H-NMR(DMSO): 10.69(s, 1H), 10.16(s, 1H), 9.53(s, 1H), 9.23(s, 1H), 8.59(d, 1H, J=8.8Hz), 8.39(d , 1H, J=8.5Hz), 8.24(d, 1H, J=6.3Hz), 7.95(d, 1H, J=6.9Hz), 7.74(t, 1H, J=7.7Hz), 7.67(t, 1H , ...

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Abstract

The present invention relates to caffeoyl naphthalene sulfamide compound. The compound is prepared with 5-acetamido-1-sodium naphthalenesulfonate as material and through reaction first with chlorosulfonic acid and then with amine compound to obtain 5-(N-substituted amino)-sulfonyl-1-naphthylamine; reaction with 3, 4-diacetylcaffeoyl chloride to obtain N-[[5-[(N-substrate)-amino]-sulfonyl]-1-naphthyl]-3, 4-diacetylcaffeoylamine; and hydrolysis to obtain N-[[5-[(N-substrate)-amino]-sulfonyl]-1-naphthyl]-caffeoylamine. The present invention also relates to the application of the compound as human immune deficiency virus integrase inhibitor.

Description

(1) Technical field [0001] The invention relates to caffeamide compounds and their synthesis, preparation methods and applications, in particular to caffeoylnaphthalenesulfonamide compounds, their preparation methods and their anti-HIV integrase effects. (2) Background technology [0002] Human immunodeficiency virus (Human immunodeficiency virus, HIV) is the pathogenic factor of AIDS (Acquiredimmuneficiency syndrome, AIDS). HIV is a single-strand ribonucleic acid (RNA) virus, and reverse transcriptase (Reverse transcriptase), protease (Protease) and integrase (Integrase) are three key enzymes in the process of HIV replication. Currently, only reverse transcriptase inhibitors and protease inhibitors are currently used in the clinical treatment of AIDS. For patients who have been treated with reverse transcriptase and protease inhibitors alone or in combination, the serum new viral load rebounds rapidly after stopping the drug, and most of the patients who have undergone che...

Claims

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Application Information

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IPC IPC(8): A61K31/18A61P31/18C07C303/38C07C311/44
Inventor 赵桂森臧恒昌徐玉文李永淑张林娜袁玉梅
Owner QINGDAO HUANGHAI PHARM CO LTD
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