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Method for synthesizing heteroaryl thiosemicarbazone antineoplastic

A technology of thiosemicarbazones and synthetic methods, which is applied in the direction of antineoplastic drugs, drug combinations, organic chemistry, etc., can solve the problems of low yield, inability to synthesize thiosemicarbazone compounds, difficult purification, etc., and achieve less purification times , The process steps are short and the raw materials are easy to obtain

Active Publication Date: 2007-02-07
SUZHOU HOMESUN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these two kinds of methods can't synthesize all thiourea compounds, and there is still the problem of low yield and difficult purification in the synthesis of some compounds

Method used

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  • Method for synthesizing heteroaryl thiosemicarbazone antineoplastic
  • Method for synthesizing heteroaryl thiosemicarbazone antineoplastic
  • Method for synthesizing heteroaryl thiosemicarbazone antineoplastic

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Synthesis of 2-pyridyl-phenylimine

[0027] A solution of 2-cyanopyridine (104 g, 1 mol) in tetrahydrofuran (200 ml) was added dropwise to a freshly prepared phenyl Grignard reagent (1.5 liters of ether-tetrahydrofuran solution, 1 mol) at room temperature, and the mixture was stirred for 5 hours . 20% aqueous ammonium chloride (600 mL) was added and stirred for another 30 minutes, then extracted with ethyl acetate (3 x 500 mL). The extract was dried with anhydrous sodium sulfate, filtered and concentrated to dryness to obtain the product which could be directly used in the next step (Example 7).

Embodiment 2

[0028] Example 2 Synthesis of 2-pyridyl-2-thienyl imine

[0029] As in Example 1, the newly prepared 2-thienyl Grignard reagent (prepared from 2-bromothiophene by a conventional method) was reacted with 2-cyanopyridine to obtain the product (directly used in Example 8).

Embodiment 3

[0030] Example 3 Synthesis of 2-pyridyl-3-pyridyl imine

[0031] A solution of 2-bromopyridine (15.8 g, 0.1 mol) in tetrahydrofuran (100 ml) was dropped into a solution of butyllithium (0.1 mol) in hexane (60 ml) and tetrahydrofuran (140 ml) at -40°C and Stir for 30 minutes to generate the 2-pyridyllithium reagent. A solution of 3-cyanopyridine (10.4 g, 0.1 mol) in THF (200 mL) was dropped into freshly prepared 2-pyridyllithium reagent at low temperature, and the mixture was stirred for 5 hours and slowly warmed to room temperature. 20% aqueous ammonium chloride (600 mL) was added and stirred for 2 hours, then extracted with ethyl acetate (3 x 500 mL). The extract was dried with anhydrous sodium sulfate, filtered and concentrated to dryness to obtain the product which could be directly used in the next step.

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Abstract

The invention discloses a synthesizing method of thiosemicarbazone antitumor agent, which is characterized by the following: shortening synthesizing path; reducing purifying times; improving total produce rate by over 99.5%; avoiding strong stimulation and poisonous methylmercaptan.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a synthesis method of heteroaromatic ring thiosemicarbazone compounds and derivatives thereof. Background technique [0002] In the previous patent application (Acceptance No. 200510027600.8), the present inventor disclosed new thiosemicarbazone compounds and their derivatives and reported their good resistance to cancer strains in vitro and to animal experiments in vivo. tumor activity. The experimental results show that there is a very close structure-activity relationship between the molecular structure of the compound in the previous invention and its tumor suppressor activity. [0003] Regarding the synthesis of thiosemicarbazone compounds, the method once used in the literature was summarized in the 200510027600.8 patent application (see reaction formula 1), and another method was also proposed (see reaction formula 2). However, these two methods cannot synthe...

Claims

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Application Information

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IPC IPC(8): C07D213/53C07D333/22C07D409/06C07C335/40A61P35/00
Inventor 谢立华王小龙高澍齐铭
Owner SUZHOU HOMESUN PHARMA
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