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2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof

A technology of nitrobenzoylhydrazone diphenyltin and phenylacetic acid, which is applied in 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone diphenyltin complex and its preparation and application fields, It can solve problems such as undiscovered compounds, and achieve the effects of simple preparation method, low cost and good anticancer activity

Inactive Publication Date: 2017-02-22
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But in 1972, Brown discovered that triphenyltin acetate Ph 3 SnOOCCH 3 Inhibits tumor growth in mice, whereas triphenyltin chloride does not
From 1972 to 1977, Dutch scholars studied a large number of organotin compounds, but found no compounds with further screening value

Method used

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  • 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof
  • 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof
  • 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone diphenyltin complex:

[0043] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.181g (1.0mmol) p-nitrobenzohydrazide, 0.165g (1.1mmol) benzoylformic acid and 15mL The solvent is 95% methanol, react at a temperature of 45~65°C for 8 hours, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-benzene Diphenyltin complexes of p-nitrobenzoylhydrazone diglycolic acid. Yield: 87.6%. Melting point: 276~278°C (dec).

[0044] Elemental analysis (C 108 h 76 N 12 o 20 sn 4 ): Calculated: C 55.51, H 3.28, N 7.19; Found: C 55.55, H 3.27, N 7.18.

[0045] FT-IR (KBr, ν / cm -1 ): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600, 1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 7, 9, 7, 8 590, 547, 451, 410.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.44 (d, J = 8.8 Hz, 2H), 8.34 (d, J =8.8 ...

Embodiment 2

[0051] Preparation of 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone diphenyltin complex:

[0052] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.181g (1.0mmol) p-nitrobenzohydrazide, 0.157g (1.05mmol) benzoylformic acid and 35mL The solvent is 95% methanol, react for 5 hours at a temperature of 45~65°C, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-benzene Diphenyltin complexes of p-nitrobenzoylhydrazone diglycolic acid. Yield: 89.5%. Melting point: 276~278°C (dec).

[0053] Elemental analysis (C 108 h 76 N 12 o 20 sn 4 ): Calculated: C 55.51, H 3.28, N 7.19; Found: C 55.55, H 3.27, N 7.18.

[0054] FT-IR (KBr, ν / cm -1 ): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600, 1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 7, 9, 7, 8 590, 547, 451, 410.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.44 (d, J = 8.8 Hz, 2H), 8.34 (d, J =8.8...

Embodiment 3

[0060] Preparation of 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone diphenyltin complex:

[0061] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.190g (1.05mmol) p-nitrobenzohydrazide, 0.173g (1.15mmol) benzoylformic acid and 25mL The solvent is 95% methanol, react at a temperature of 45~65°C for 24 hours, cool, filter, and control the solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-benzene Diphenyltin complexes of p-nitrobenzoylhydrazone diglycolic acid. Yield: 89.7%. Melting point: 276~278°C (dec).

[0062] Elemental analysis (C 108 h 76 N 12 o 20 sn 4 ): Calculated: C 55.51, H 3.28, N 7.19; Found: C 55.55, H 3.27, N 7.18.

[0063] FT-IR (KBr, ν / cm -1 ): 3105, 3070, 3053, 3020, 2991, 1695, 1616, 1600, 1527, 1479, 1431, 1384, 1340, 1321, 1251, 1170, 1155, 1087, 1012, 869, 7, 9, 7, 8 590, 547, 451, 410.

[0064] 1 H NMR (500 MHz, CDCl3 , δ / ppm): 8.44 (d, J = 8.8 Hz, 2H), ...

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Abstract

The invention discloses a 2-carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex. The complex is represented by structural formula (I); and Ph in the structural formula (I) is a phenyl group. The invention also discloses a preparation method of the 2-carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and an application of the complex in the preparation of anticancer medicines.

Description

technical field [0001] The invention relates to a 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone diphenyltin complex and a preparation method thereof, and the 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone Application of diphenyltin complexes in the preparation of anticancer drugs. Background technique [0002] Organotin is a class of metal-organic compounds containing Sn-C bonds. Researchers have noticed the in vitro anticancer activity of organotin compounds long ago. Research on the antitumor activity of organotin(IV) compounds dates back to 1929. In 1967, Kanisawa et al. considered that tin chloride was ineffective against primary tumors in mice and rats. But in 1972, Brown discovered that triphenyltin acetate Ph 3 SnOOCCH 3 Can inhibit tumor growth in mice, but triphenyltin chloride does not. From 1972 to 1977, Dutch scholars studied a large number of organotin compounds, but no compounds with further screening value were found. They continued in-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00
CPCC07F7/2284
Inventor 蒋伍玖谭宇星邝代治冯泳兰朱小明庾江喜张复兴
Owner HENGYANG NORMAL UNIV
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