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Benzoic acid nitrogen mustard derivative as well as preparation method and application thereof

A technology of benzoen mustard and its derivatives, which is applied in the field of benzoen mustard derivatives and their preparation and application, and can solve the problems of high toxicity and the like

Inactive Publication Date: 2010-04-14
南京大学中国医药城研发中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the currently used aromatic nitrogen mustard antineoplastic drugs, although they have higher alkylation efficiency, they are more toxic

Method used

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  • Benzoic acid nitrogen mustard derivative as well as preparation method and application thereof
  • Benzoic acid nitrogen mustard derivative as well as preparation method and application thereof
  • Benzoic acid nitrogen mustard derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Preparation of N-butyl-4-(two-(2-chloroethyl)amino)benzamide (compound 1)

[0025]

[0026] Get 1mmol benzoen mustard (referring to Chemical Biology & Drug Design, 2007, 70 (3), 216-226; Chemical Reagents, 2004, 26 (3), 183-184 method to prepare benzoic acid mustard) dissolved in 12mL dimethicone In methyl chloride, add 1 mmol N, N-dicyclohexylcarbodiimide (DCC) under stirring at room temperature and stir for 10 min, then add 1 mmol n-butylamine and 0.5 mmol 4-dimethylaminopyridine (DMAP) respectively and stir at room temperature 24h. Filter, wash the filter cake (10mL×3) with dichloromethane, combine the organic phases, evaporate the solvent under reduced pressure, use ethyl acetate-petroleum ether (V:V=1:3-1:8) as the eluent, and use a silica gel column After separation, the solvent was distilled off under reduced pressure to obtain the target compound. White powder, yield 85%. M.p.: 52-54°C. 1 H NMR (300MHz, CDCl 3 ): 0.95(t, J=7.3Hz, 3H); 1.36-1.46...

Embodiment 2

[0027] Example 2: Preparation of N-tert-butyl-4-(bis-(2-chloroethyl)amino)benzamide (compound 2)

[0028]

[0029] The preparation method is the same as in Example 1. The title compound was obtained by replacing n-butylamine with tert-butylamine. White powder, yield 80%. M.p.: 141-143°C. 1 H NMR (300MHz, CDCl 3 ): 1.28(s, 9H); 3.63(t, J=6.6Hz, 4H); 3.76(t, J=6.6Hz, 4H); 5.83(s, 1H); 6.68(d, J=8.9Hz, 2H ); 7.70 (d, J=8.9Hz, 2H); MS (ESI): 318.3 (C 15 h 22 Cl 2 N 2 O, [M+H] + ).Anal.Calcd for C 15 h 22 Cl 2 N 2 O: C, 56.79; H, 6.99; N, 8.83%; Found: C, 56.88; H, 6.72; N, 8.70%.

Embodiment 3

[0030] Example 3: Preparation of N-cyclopentyl-4-(two-(2-chloroethyl)amino)benzamide (compound 3)

[0031]

[0032] The preparation method is the same as in Example 2. The target compound was obtained by replacing n-butylamine with cyclopentylamine. White powder, yield 81%. M.p.: 84-86°C. 1 H NMR (300MHz, CDCl 3 ): 1.67-1.69(m, 4H); 1.70-1.73(m, 4H); 3.64(t, J=6.8Hz, 4H); 3.78(t, J=6.8Hz, 4H); 4.33-4.45(m, 1H); 5.90(s, 1H); 6.67(d, J=8.9Hz, 2H); 7.68(d, J=8.9Hz, 2H).MS(ESI): 330.3(C 16 h 22 Cl 2 N 2 O, [M+H] + ).Anal.Calcd for C 16 h 22 Cl 2 N 2 O: C, 58.36; H, 6.73; N, 8.51%; Found: C, 58.19; H, 6.58; N, 8.64%.

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Abstract

The invention relates to a benzoic acid nitrogen mustard derivative which has the following formula: R1 is 4-CH3-C6H5, 4-CH3O-C6H5, 4-CH(CH3)2-C6H5, 4-F-C6H5, 4-Cl-C6H5, 4-Br-C6H5, 4-NO2-C6H5, 2-F-C6H5, 2-Cl-C6H5, 2-Br-C6H5, n-butyl, tertiary butyl and n-dodecyl, and R2 is H; or R1 is CH3-, and R2 is C6H5-; or R1 and R2 are both n-propyl and n-butyl. The benzoic acid nitrogen mustard derivative has remarkable inhibiting effect for human oral cavity epicuticula cancer cell strain (KB) and human leukaemia cell strain (K562) so that the benzoic acid nitrogen mustard derivative can be applied in preparing antitumor medicaments. The invention also discloses a preparation method of the benzoic acid nitrogen mustard derivative.

Description

technical field [0001] The invention relates to a benzoic acid mustard derivative, a preparation method thereof and an application as an anticancer drug. Background technique [0002] At present, there are many types of drugs for the treatment of malignant tumors, such as nitrogen mustards, pyrimidines, platinums, porphyrins and so on. Among various antineoplastic drugs, nitrogen mustard compounds are an earlier and important class of antineoplastic drugs, and play an important role in the treatment of tumors. [0003] Nitrogen mustard antineoplastic drugs are the general term for β-chloroethylamine compounds, including mono-β-chloroethylamines and double-β-chloroethylamines. Nitrogen mustard compounds, as an important class of antineoplastic drugs, have been used clinically in many ways. Throughout its structure, nitrogen mustard antitumor compounds are generally divided into two parts: the alkylation part and the carrier part. The alkylation part is the functional group...

Claims

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Application Information

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IPC IPC(8): C07C237/30C07C237/38C07D295/13C07C237/40A61K31/166A61K31/5375A61K31/167A61P35/00A61P35/02
Inventor 朱海亮郑庆忠程魁焦庆才
Owner 南京大学中国医药城研发中心
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