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3-[2-(aryl propylenine)hydrazino]-ethyl benzoate compound and application thereof

A technology of ethyl benzoate, propenylidene, applied in the fields of medicinal chemistry and pharmacotherapeutics

Inactive Publication Date: 2015-04-15
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These auxiliary proteins include human proteins LEDGF / p75, INI1, HSP60, etc., but currently only the role of LEDGF / p75 in the integration process has been studied clearly

Method used

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  • 3-[2-(aryl propylenine)hydrazino]-ethyl benzoate compound and application thereof
  • 3-[2-(aryl propylenine)hydrazino]-ethyl benzoate compound and application thereof
  • 3-[2-(aryl propylenine)hydrazino]-ethyl benzoate compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 3-[2-((naphthalene-1-yl)-propenylidene)hydrazino]-benzoic acid (intermediate III-1)

[0029]

[0030] 152 mg of 3-hydrazinobenzoic acid was dissolved in 4.5 mL of absolute ethanol, 182 mg of 3-(naphthalene-1-yl)acrolein (compound II-1) was added, and refluxed for 2 hours. After the reaction was completed, after cooling to room temperature, a solid precipitated out in the solution. After suction filtration, the solid was washed with a mixed solution of ethyl acetate and petroleum ether (ethyl acetate: petroleum ether = 1:20), and dried to obtain the title compound, 252 mg of a light yellow solid, with a yield of 80%.

[0031] 1 H-NMR (400MHz, DMSO-d 6 )δ: 7.15 (dd, J 1 =16Hz,J 2=9.2Hz, 1H), 7.20-7.27(m, 1H), 7.34(d, J=4.8Hz, 2H), 7.49-7.63(m, 3H), 7.67(s, 1H), 7.73(d, J= 16Hz, 1H), 7.88(d, J=8.4Hz, 1H), 7.90-7.99(m, 3H), 8.35(d, J=8.4Hz, 1H), 10.60(s, 1H), 12.83(s, 1H ).

Embodiment 2

[0033] Preparation of 3-[2-((naphthalene-1-yl)-propenylidene)hydrazino]-benzoic acid ethyl ester (compound I-1)

[0034]

[0035] Dissolve 102 mg of 3-[2-((naphthalene-1-yl)-propenylidene)hydrazino]-benzoic acid (Intermediate III-1) in 2mL of anhydrous dichloromethane, and add 105 mg of dicyclohexylcarbodiimide, stirred for 20 minutes, then moved to room temperature, added 33 mg of 4-dimethylaminopyridine and 8 mL of absolute ethanol, and reacted at room temperature for 12 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was separated by column chromatography to obtain 80 mg of a yellow solid (Compound I-1), with a yield of 72%.

[0036] 1 H-NMR (400MHz, DMSO-d 6 )δ: 1.33(t, J=7.2Hz, 3H), 4.32(q, J=7.2Hz, 2H), 7.14(dd, J 1 =16Hz,J 2 =9.2Hz, 1H), 7.23-7.30(m, 1H), 7.34-7.39(m, 2H), 7.50-7.64(m, 3H), 7.66(s, 1H), 7.74(d, J=16Hz, 1H ), 7.88(d, J=8.4Hz, 1H), 7.90-7.98(m, 3H), 8.35(d, J=8.4Hz, 1H), 10.63(s, 1H); MS(EI) m / z 344...

Embodiment 3

[0038] Preparation of 3-[2-((3-methoxy-4-acetoxyphenyl)-propenylidene)hydrazino]-benzoic acid ethyl ester (compound I-2)

[0039]

[0040] Except for replacing 3-(naphthalene-1-yl)acrolein with 3-(3-methoxy-4-acetoxyphenyl)acrolein, the rest of the required raw materials, reagents and preparation methods are the same as in Example 1 -2, the title compound was obtained, 14 mg of khaki solid, yield 24%.

[0041] 1 H-NMR (400MHz, DMSO-d 6 )δ: 1.33(t, J=7.2Hz, 3H), 2.26(s, 3H), 3.84(s, 3H), 4.32(q, J=7.2Hz, 2H), 6.82(d, J=16Hz, 1H ), 7.05(s, J=8.4Hz, 1H), 7.08-7.16(m, 2H), 7.18-7.23(m, 1H), 7.30-7.36(m, 2H), 7.38(s, 1H), 7.64( s, 1H), 7.75 (d, J=9.2Hz, 1H), 10.54 (s, 1H); MS (EI) m / z 382.2 (M + ).

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Abstract

The invention relates to a 3-[2-(aryl propylenine)hydrazino]-ethyl benzoate compound and an application thereof. The 3-[2-(aryl propylenine)hydrazino]-ethyl benzoate compound is a compound as shown in the formula I or a pharmaceutically acceptable salt (refer to the claim 1 for the specific structure). The compound provided by the invention has strong inhibitory activity on the close related protein-protein interaction in a human immunodeficiency virus gene integration process, namely the human immunodeficiency virus (HIV)-1 integrase and lens epithelium derived growth factor (LEDGF) / p75 interaction. The result proves that the compound provided by the invention is hopefully developed to be a novel target anti-acquired immune deficiency syndrome pharmaceutical for the protein-protein interaction.

Description

technical field [0001] The invention relates to 3-[2-(arylpropenylidene)hydrazino]-benzoic acid ethyl ester compounds and their composition and use, which belong to the field of medicinal chemistry and drug therapeutics. Background technique [0002] Human immunodeficiency syndrome (AIDS) is a systemic immunodeficiency syndrome caused by human immunodeficiency virus (HIV) infection. Since the first AIDS case was confirmed by American medical researchers in June 1981, HIV has spread rapidly from a few high-incidence areas to more than 200 countries. At present, AIDS has caused 25 million deaths worldwide, and the total number of AIDS patients and virus carriers in the world has reached more than 30 million. AIDS has become one of the diseases that seriously threaten human health in the world. Since the 1990s, with the in-depth study of the molecular biology of the virus and its infection process, as well as the innovation of drug development technology, anti-HIV drugs have b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C243/22C07C241/02A61K31/192A61K31/235A61P31/18
CPCY02P20/10
Inventor 唐赟李剑黄瑾郑庶李蹊胡国平
Owner EAST CHINA UNIV OF SCI & TECH