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N, N-disubstituted-N'-phthaloyl group-1, 3-diamine derivative and preparation method thereof

A technology of phthaloyl and diamine derivatives, applied in organic chemistry, antiviral agents, etc., to achieve the effect of increasing diversity

Active Publication Date: 2014-05-21
SHANGHAI SYNTHEALL PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly solve the technical problems of the expansion of N, N-disubstituted-N'-phthaloyl-1, 3-diamine derivatives and the screening of their drug activity structure-activity relationship

Method used

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  • N, N-disubstituted-N'-phthaloyl group-1, 3-diamine derivative and preparation method thereof
  • N, N-disubstituted-N'-phthaloyl group-1, 3-diamine derivative and preparation method thereof
  • N, N-disubstituted-N'-phthaloyl group-1, 3-diamine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1 : N, N-dibenzyl-N'-phthaloyl-1, 3-diamine I-a preparation of

[0060]

[0061] Steps:

[0062] In a 250ml three-neck reaction flask, sodium (0.18g, 7.8mmol) was dissolved in absolute ethanol (100ml), cooled to 0°C with an ice bath, and the phthalimide 1 (11 g, 74.8 mmol) was added, followed by dropwise addition of acrolein (5.3 g, 93.6 mmol), and the reaction was stirred at room temperature for 2 hours after the drop was complete. The reaction solution was quenched with glacial acetic acid, extracted three times with ethyl acetate, and the organic phase was dried and concentrated to dryness to obtain a crude product. The crude product was purified by column chromatography to obtain 5.9 g of N-phthaloyl-3-aminopropanal 2 , yield 39%. HNMR (CDCl 3 ) d: 9.58 (s, 1H), 7.23-7.26 (m, 4H), 4.60-4.62 (m, 2H), 2.98-3.18 (m, 2H).

[0063] N-phthaloyl-3-aminopropanal 2 (2 g, 10 mmol) and triethylamine (2.1 ml) were dissolved in 1,2-dichloroethane (150 ml) so...

Embodiment 2

[0065] Example 2 : N-benzenesulfonyl-N-benzyl-N'-phthaloyl-1, 3-diamine I-b preparation of

[0066]

[0067] Steps:

[0068] N-benzyl-N'-phthaloyl-1,3-diamine 3 (2 g, 6.8 mmol) and triethylamine (2.1 ml) were dissolved in dichloromethane (150 ml) solution, cooled to 0 ° C with an ice bath, and then benzenesulfonyl chloride (952 mg, 6.8 mmol) was added dropwise , After the dropwise reaction was stirred at room temperature for 2 hours. The reaction solution was quenched with saturated aqueous sodium bicarbonate, extracted three times with dichloromethane, and the organic phase was dried and concentrated to dryness to obtain a crude product. The crude product was purified by column chromatography to obtain 2.9 g of N-benzenesulfonyl-N-benzyl-N'-phthaloyl-1,3-diamine I-b , yield 65%. HNMR (CD 3 OD) d: 7.73-7.77 (m, 4H), 7.43-7.65 (m, 5H), 7.07-7.15 (m, 5H), 4.25 (s, 2H), 3.42-3.45 (m, 2H), 3.01-3.10 (m, 2H), 1.62-1.69 (m, 2H).

Embodiment 3

[0069] Example 3 : N-3-pyridinesulfonyl-N-4-benzyl-N'-phthaloyl-1, 3-diamine I-c preparation of

[0070]

[0071] Steps:

[0072] N-benzyl-N'-phthaloyl-1,3-diamine 3 (2 g, 6.8 mmol) and triethylamine (2.1 ml) were dissolved in dichloromethane (150 ml) solution, cooled to 0 ° C with an ice bath, and then 3-pyridinesulfonyl chloride (1.2 g, 6.8 ml) was added dropwise mol), and the reaction was stirred at room temperature for 2 hours after dropping. The reaction solution was quenched with saturated aqueous sodium bicarbonate, extracted three times with dichloromethane, and the organic phase was dried and concentrated to dryness to obtain a crude product. The crude product was purified by column chromatography to obtain 1.9 g of N-3-pyridinesulfonyl-N-4-benzyl-N'-phthaloyl-1,3-diamine I-c , yield 65%. HNMR (CD 3 OD) d: 8.97-9.02 (m, 1H), 8.82-8.86 (m, 1H), 8.34-8.38 (m, 1H) 7.81-7.85 (m, 4H), 7.68-7.72 (m, 1H), 7.19- 7.22 (m, 2H), 7.12 -7.16 (m, 3H), 4.34-4.38 (m, 2H...

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Abstract

The invention relates to N, N-disubstituted-N'-phthaloyl group-1, 3-diamine derivative and preparation method thereof, which mainly solve the technical problems related to the expanding of the N, N-disubstituted-N'-phthaloyl group-1, 3-diamine derivative and the screening of the structure-activity relationship of the N, N-disubstituted-N'-phthaloyl group-1, 3-diamine derivative to the drug activity. The structural general formula is shown in the description, wherein X is a substituted functional group, and selects from one of H, Cl-Cl0 straight chain, or alkyl group containing a substituent group side chain, alkyl sulfonyl or alkyl formoxyl, aryl group, aromatic sulfonyl, aromatic formoxyl and heteroaromatic sulfonyl; and Y is a substituted functional group and selects from one of H, Cl-Cl0 straight chain, or alkyl group containing a substituent group side chain, alkyl sulfonyl or alkyl formoxyl, aryl group, aromatic sulfonyl, aromatic formoxyl and heteroaromatic sulfonyl.

Description

technical field [0001] The present invention relates to N, N-disubstituted-N'-phthaloyl-1, 3-diamine derivatives and a preparation method thereof. Background technique [0002] Alkane diamines have a wide range of application values ​​in the synthesis of epoxy resin curing agents, oil passivators, corrosion inhibitors, and pharmaceutical intermediates. Especially in the process of drug research, alkanediamine, as a bridging unit, can effectively link and integrate key pharmacophore units into a specific structure to form molecules with special spatial configuration / conformation, which can match The spatial structure of different biomacromolecules in organisms produces corresponding biological activities or effects, so it has broad application prospects. Compounds containing alkanediamine structural units have been proved by many experiments to have various biological activities. The following are some examples that have been disclosed in some documents and are closely relat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48C07D401/12C07D403/12C07D401/14C07D413/14C07D413/12A61P31/14
Inventor 董飞彭宣嘉蔡亚仙尹科李宁林天伟黎健陈曙辉
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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