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2-oxobutyric acid p-nitrobenzoyl hydrazone dibenzyl tin complex and preparation method and application thereof

A technology of nitrobenzoylhydrazone diphenyltin and carbonyl butyric acid, which is applied in the fields of tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve the problems of undiscovered compounds, and achieve simple preparation methods and anticancer activity The effect of high and good anticancer activity

Active Publication Date: 2017-02-08
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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-oxobutyric acid p-nitrobenzoyl hydrazone dibenzyl tin complex and preparation method and application thereof
  • 2-oxobutyric acid p-nitrobenzoyl hydrazone dibenzyl tin complex and preparation method and application thereof
  • 2-oxobutyric acid p-nitrobenzoyl hydrazone dibenzyl tin complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0043] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.181g (1.0mmol) p-nitrobenzohydrazide, 0.112g (1.1mmol) 2-butanone acid and 15mL of anhydrous methanol as a solvent, react for 8 hours at a temperature of 45~65°C, 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-carbonylbutyric acid p- Nitrobenzoylhydrazone diphenyltin complexes. Yield: 81.1%. Melting point: 220~222°C (dec).

[0044] Elemental analysis (C 48 h 46 N 6 o 12 sn 2 ): Calculated: C 50.73, H 4.08, N 7.40; Found: C 50.82, H 4.11, N 7.45.

[0045] FT-IR (KBr, ν / cm -1 ): 3506, 3057, 2972, 2937, 1687, 1597, 1529, 1431, 1338, 804, 717, 688, 588, 551, 453, 416.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.49 (d, J =8.8 Hz, 2H), 8.34 (d, J =8.8Hz, 2H), 7.79-7.81 (m, 4H), 7.47-7.51 (m, 6H), 3.12-3.17 (q, J =7....

Embodiment 2

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

[0052] Add 0.344g (1.0mmol) diphenyl tin dichloride, 0.181g (1.0mmol) p-nitrobenzohydrazide, 0.107g (1.05mmol) 2-butanone acid and 35mL of anhydrous methanol as a solvent, react for 5 hours at a temperature of 45~65°C, 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-carbonylbutyric acid p- Nitrobenzoylhydrazone diphenyltin complexes. Yield: 86.5%. Melting point: 220~222°C (dec).

[0053] Elemental analysis (C 48 h 46 N 6 o 12 sn 2 ): Calculated: C 50.73, H 4.08, N 7.40; Found: C 50.82, H 4.11, N 7.45.

[0054] FT-IR (KBr, ν / cm -1 ): 3506, 3057, 2972, 2937, 1687, 1597, 1529, 1431, 1338, 804, 717, 688, 588, 551, 453, 416.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.49 (d, J =8.8 Hz, 2H), 8.34 (d, J =8.8Hz, 2H), 7.79-7.81 (m, 4H), 7.47-7.51 (m, 6H), 3.12-3.17 (q, J =...

Embodiment 3

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

[0061] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.190g (1.05mmol) p-nitrobenzohydrazide, 0.117g (1.15mmol) 2-butanone acid and 25mL of anhydrous methanol as a solvent, react for 24 hours at a temperature of 45~65°C, cool, filter, and control solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonylbutyric acid p- Nitrobenzoylhydrazone diphenyltin complexes. Yield: 85.4%. Melting point: 220~222°C (dec).

[0062] Elemental analysis (C 48 h 46 N 6 o 12 sn 2 ): Calculated: C 50.73, H 4.08, N 7.40; Found: C 50.82, H 4.11, N 7.45.

[0063] FT-IR (KBr, ν / cm -1 ): 3506, 3057, 2972, 2937, 1687, 1597, 1529, 1431, 1338, 804, 717, 688, 588, 551, 453, 416.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.49 (d, J =8.8 Hz, 2H), 8.34 (d, J =8.8Hz, 2H), 7.79-7.81 (m, 4H), 7.47-7.51 (m, 6H), 3.12-3.17 (q, J =7.6...

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Abstract

The invention discloses a 2-oxobutyric acid p-nitrobenzoyl hydrazone dibenzyl tin complex, which is a complex having the structural formula (I) as shown in the specification. In the structural formula (I), R is phenyl group. The invention also discloses a preparation method of the 2-oxobutyric acid p-nitrobenzoyl hydrazone dibenzyl tin complex and application of the complex in the preparation of an anti-cancer drug.

Description

technical field [0001] The invention relates to a 2-carbonylbutyric acid p-nitrobenzoylhydrazone diphenyltin complex and a preparation method thereof, and the preparation of the 2-carbonylbutyric acid p-nitrobenzoylhydrazone diphenyltin complex Application in 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-depth research and fi...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61K31/32A61K31/555A61P35/00
CPCC07B2200/13C07F7/2284C07F7/2296
Inventor 谭宇星蒋伍玖庾江喜朱小明张志坚邝代治张复兴
Owner HENGYANG NORMAL UNIV
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