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Compound in category of aryl methylamino dithio formic ether, preparation method and application

An aminodithiocarboxylic acid and ester compound technology, which can be used in the directions of heterocyclic compound active ingredients, ester active ingredients, drug combinations, etc., and can solve the problem of little anti-tumor activity.

Inactive Publication Date: 2006-02-01
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few studies on the antitumor activity of these compounds

Method used

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  • Compound in category of aryl methylamino dithio formic ether, preparation method and application
  • Compound in category of aryl methylamino dithio formic ether, preparation method and application
  • Compound in category of aryl methylamino dithio formic ether, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation of embodiment 1 compound 1

[0043]

[0044] (compound 1)

[0045] 2-Fufurylamine (0.49g, 5×10 -3 mol) was dissolved in acetone (or dimethylformamide) (5mL), and anhydrous potassium phosphate (1.06g, 5×10 -3 mol), carbon disulfide (1mL, excess), after 30min, add 2-bromoacetaldehyde diethyl acetal (0.99g, 5×10 -3 mol) of acetone solution. After stirring at room temperature for 2 h, the reaction was stopped. After filtration, the filtrate was concentrated, 20 mL of water was added, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with anhydrous calcium chloride, then concentrated by rotary evaporation to obtain light yellow liquid compound 1 (1.32 g, 91%).

[0046] Elemental Analysis: C 12 h 19 NO 3 S 2 Calculated (%): C 49.80, H 6.62, N 4.84; Found (%): C 49.56, H 6.50, N 5.12. 1 H-NMR (CDCl 3 , δ): 1.18(t, 6H), 3.29(d, 2H), 3.52~3.75(m, 4H), 4.64(t, 1H), 4.86(d, 2H), 6.34~6.36(m, 2H), 7.38 (t, 1H), ...

Embodiment 2

[0047] The preparation of embodiment 2 compound 2

[0048]

[0049] (compound 2)

[0050] The synthesis and post-treatment methods of compound 2 are the same as those of compound 1, except that 2-bromoacetaldehyde diethyl acetal is replaced by o-chlorobenzyl chloride.

[0051] Yield: 93%, pale yellow liquid. Elemental Analysis: C 13 h 12 ClNOS 2 Calculated (%): C 52.43, H 4.06, N 4.70; Found (%): C 52.64, H 4.46, N 5.01. 1 H-NMR (CDCl 3 , δ) 4.58-4.88 (m, 2H), 6.31-6.34 (m, 2H), 7.17-7.56 (m, 7H).

Embodiment 3

[0052] The preparation of embodiment 3 compound 3

[0053]

[0054] (compound 3)

[0055] The synthesis and post-treatment methods of compound 3 are the same as those of compound 1, except that 2-bromoacetaldehyde diethyl acetal is replaced by monochloroacetone.

[0056] Yield: 96%. Rhombic white crystal, mp 75~77℃. Elemental Analysis: C 9 h 11 NO 2 S 2 Calculated (%): C 47.14, H 4.83, N 6.11; found (%): C 47.38, H 4.82, N 6.18. FAB(MH + ): calculated value 230.3; measured value 230.1.

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Abstract

An antineoplastic arylmethylamino bithioformate compound, or its medicinal salt, its preparing process, the medicinal composition containing it, and its application are disclosed.

Description

technical field [0001] The present invention relates to a class of aminodithiocarbamate compounds or their pharmaceutically acceptable salts, in particular to arylmethylcarbamodithioate compounds or their pharmaceutically acceptable salts, their preparation methods and their use in the preparation of antitumor drugs in the application. Background technique [0002] Carbamate compounds are widely used in many fields, especially in the field of pesticides, they are often used as fungicides. However, there are few studies on the antitumor activity of these compounds. [0003] Recently, Gerhauser C et al. reported in Cancer Research 57, 272-278, 1997 that a kind of isothiocyanate compound Brassinium was isolated from Brassicaceae plants, which has a strong tumor prevention effect. Further structural modification of this compound led to the discovery of Sulforamate, a carbamate compound with stronger tumor prevention effect. Contents of the invention [0004] The object of t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C333/24C07D277/16C07D217/26C07D209/44C07D317/18C07D407/12A61K31/27A61K31/341A61K31/36A61K31/427A61K31/426A61K31/47A61P35/00
Inventor 李润涛卫军王一强葛泽梅崔景荣程铁明
Owner PEKING UNIV