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Synthesis of dihydroxytin mononuclear p-chloro, p-fluoro or p-methoxyl-benzoyl hydroxamate complex

A technology of dihydrocarbyltin methoxybenzoyl hydroxamate and dihydrocarbyltin hydroxamate, which is applied in the fields of tin organic compounds and organic chemistry, and can solve unfavorable industrial production, difficulty in developing drugs, and equipment requirements advanced questions

Inactive Publication Date: 2004-09-22
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Although a series of new complexes synthesized with benzoic acid and its derivative benzoylhydroxamic acid as ligands have anticancer activity against solid tumors, especially MCF-7 breast cancer and WiDr colon cancer, it is close to the first-line clinical anticancer activity. The drug cisplatin, but their toxic side effects are too strong to be developed into a drug
And the synthetic technique is more complicated, and equipment requirement is high, is unfavorable for industrial production (seeing document Coord.Chem.Rev.1996,151,41; Appl.Organomet.Chem, 1993,7,201; 1994,8,19; 1995,9 , 639; 1995, 9, 251)

Method used

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  • Synthesis of dihydroxytin mononuclear p-chloro, p-fluoro or p-methoxyl-benzoyl hydroxamate complex
  • Synthesis of dihydroxytin mononuclear p-chloro, p-fluoro or p-methoxyl-benzoyl hydroxamate complex
  • Synthesis of dihydroxytin mononuclear p-chloro, p-fluoro or p-methoxyl-benzoyl hydroxamate complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Complex [Bu n 2 Sn(p-Cl-C 6 h 5 -CONHOH) 2 ] of synthesis, the structure is as mentioned above:

[0095] 1. Synthetic route

[0096]

[0097]

[0098]

[0099] 2. Preparation method

[0100] (1) Ligand HL 1 ——p-Cl-C 6 h 5 -Synthesis of CONHOH:

[0101] Dissolve 2.5 grams (62 mmol) of sodium hydroxide in 15 ml of ice water, and slowly add 2.2 grams (32 mmol) of hydroxylamine hydrochloride in 30 ml of aqueous solution with stirring, then add 20 mmol of methyl p-chlorobenzoate (p-Cl-C 6 h 5 -COOCH 3 ), stirred at room temperature. Acidify to pH 7.5 with 5M HCl in an ice bath, a white precipitate precipitates, and is suction filtered. Recrystallize in a methanol / water mixed solvent, dry to constant weight, and obtain the product ligand HL 1 .

[0102] (2) Synthesis of mononuclear p-chlorobenzoyl hydroxamic acid dihydrocarbyl tin complex:

[0103] Will Bu n 2 SnCl 2 (0.303g 1.0mmol) added to HL 1 (0.344-g, 2.0 mmol) in KOH (0.112 g, 2...

Embodiment 2

[0107] Complex [Bu n 2 Sn(p-CH 3 O-C 6 h 5 -CONOH) 2 ] of synthesis, the structure is as mentioned above:

[0108] 1. Synthetic route

[0109]

[0110]

[0111]

[0112] 2. Preparation method

[0113] (1) Ligand (HL 3 )——p-CH 3 O-C 6 h 5 -Synthesis of CONHOH:

[0114] Dissolve 2.5 grams (62 mmol) of sodium hydroxide in 15 ml of ice water, and slowly add 2.2 grams (32 mmol) of hydroxylamine hydrochloride in 30 ml of aqueous solution with stirring, then add 20 mmol of methyl p-methoxybenzoate (p-CH 3 O-C 6 h 5 -COOCH 3 ), stirred at room temperature. Acidify to pH 7.5 with 5M HCl in an ice bath, a white precipitate precipitates, and is suction filtered. Recrystallize in a methanol / water mixed solvent, dry to constant weight, and obtain the product ligand HL 3 .

[0115] (2) Synthesis of mononuclear p-methoxybenzoyl hydroxamic acid dihydrocarbyl tin complex:

[0116] Will Bu n 2 SnCl 2 (0.576g, 1.8mmol) added to HL 3 (0.504g, 3.0mmol) i...

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Abstract

The invention relates to the match of mononuclear p-chloro (or p-fluoro, or p-methoxyl)-dihydroxy tin benzoyl hydroxamate and its synthesizing process. The said match features broad spectrum, low poison and high anticancer activity.

Description

technical field [0001] The invention relates to a series of synthesis methods of organotin complexes with anticancer activity. Specifically, it is the synthesis of mononuclear p-chlorine, p-fluorine and p-methoxybenzoyl hydroxamic acid dihydrocarbyl tin complexes. Background technique [0002] Although a series of new complexes synthesized with benzoic acid and its derivative benzoylhydroxamic acid as ligands have anticancer activity against solid tumors, especially MCF-7 breast cancer and WiDr colon cancer, it is close to the first-line clinical anticancer activity. Drug cisplatin, but their toxic side effects are very strong, it is difficult to develop into drugs. And the synthetic technique is more complicated, and equipment requirement is high, is unfavorable for industrial production (seeing document Coord.Chem.Rev.1996,151,41; Appl.Organomet.Chem, 1993,7,201; 1994,8,19; 1995,9 , 639; 1995, 9, 251). Contents of the invention [0003] In order to solve the enzyme de...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C259/10C07F7/22
Inventor 李青山韩玲革黄计军赵敬华许华
Owner SHANXI MEDICAL UNIV
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