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2-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex and preparation method and application thereof

A technology of methoxybenzoylhydrazone diphenyltin and carbonylpropionic acid, which is applied in the application field of preparing anticancer drugs, can solve the problems of undiscovered compounds, etc., and achieve simple preparation methods, good anticancer activity, and low cost. low effect

Inactive Publication Date: 2017-01-18
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-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex and preparation method and application thereof
  • 2-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex and preparation method and application thereof
  • 2-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-oxopropionic acid p-methoxybenzoylhydrazone diphenyltin complex:

[0043] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.166g (1.0mmol) p-methoxybenzohydrazide, 0.115g (1.05mmol) sodium pyruvate and 15mL The solvent is anhydrous methanol, reacted for 8 hours at a temperature of 50~65°C, cooled, filtered, and controlled solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonylpropionic acid p-formaldehyde Oxybenzoylhydrazone diphenyltin complexes. Yield: 87.2%. Melting point: 96~98°C (dec).

[0044] Elemental analysis (C 48 h 48 N 4 o 10 sn 2 ): Calculated: C 53.46, H 4.49, N 5.20; Found: C 53.50, H 4.51, N 5.21.

[0045] FT-IR (KBr, ν / cm -1 ): 3448, 3055, 2956, 2933, 2837, 1687, 1602, 1479, 1386, 1253, 1170, 1072, 844, 731, 696, 626, 594, 541, 511, 455.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.31 (d, J =9.0 Hz, 2H), 7.80-7.82 (m,4H), 7.44-7.47 (m, 6H), 7.01 (d, ...

Embodiment 2

[0051] Preparation of 2-oxopropionic acid p-methoxybenzoylhydrazone diphenyltin complex:

[0052] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.174g (1.05mmol) p-methoxybenzohydrazide, 0.126g (1.15mmol) sodium pyruvate and 35mL The solvent is anhydrous methanol, react for 5 hours at a temperature of 50~65°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-oxopropionic acid p-formaldehyde Oxybenzoylhydrazone diphenyltin complexes. Yield: 86.0%. Melting point: 96~98°C (dec).

[0053] Elemental analysis (C 48 h 48 N 4 o 10 sn 2 ): Calculated: C 53.46, H 4.49, N 5.20; Found: C 53.50, H 4.51, N 5.21.

[0054] FT-IR (KBr, ν / cm -1 ): 3448, 3055, 2956, 2933, 2837, 1687, 1602, 1479, 1386, 1253, 1170, 1072, 844, 731, 696, 626, 594, 541, 511, 455.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.31 (d, J =9.0 Hz, 2H), 7.80-7.82 (m,4H), 7.44-7.47 (m, 6H), 7.01 (d, J =9.0 H...

Embodiment 3

[0060] Preparation of 2-oxopropionic acid p-methoxybenzoylhydrazone diphenyltin complex:

[0061] Add 1.720g (5.0mmol) diphenyltin dichloride, 0.847g (5.1mmol) p-methoxybenzohydrazide, 0.605g (5.5mmol) sodium pyruvate and 25mL Solvent anhydrous methanol, react for 20 hours at a temperature of 50~65°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-carbonylpropionic acid p-formaldehyde Oxybenzoylhydrazone diphenyltin complexes. Yield: 85.8%. Melting point: 96~98°C (dec).

[0062] Elemental analysis (C 48 h 48 N 4 o 10 sn 2 ): Calculated: C 53.46, H 4.49, N 5.20; Found: C 53.50, H 4.51, N 5.21.

[0063] FT-IR (KBr, ν / cm -1 ): 3448, 3055, 2956, 2933, 2837, 1687, 1602, 1479, 1386, 1253, 1170, 1072, 844, 731, 696, 626, 594, 541, 511, 455.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.31 (d, J =9.0 Hz, 2H), 7.80-7.82 (m,4H), 7.44-7.47 (m, 6H), 7.01 (d, J =9.0 Hz, 2H),...

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Abstract

The invention discloses a 2-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex. The 2-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex is a complex which has the following structural formula (I) (please see the formula in the description), wherein R represents a phenyl group. The invention further discloses a preparation method of the 2-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex and application of the 2-oxo-propionic acid p-methoxyl benzoyl hydrazone diphenyl tin complex in preparation of anti-cancer drugs.

Description

technical field [0001] The invention relates to a 2-carbonylpropionic acid p-methoxybenzoylhydrazone diphenyltin complex and a preparation method thereof, and the 2-carbonylpropionic acid p-methoxybenzoylhydrazone diphenyltin complex Application 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-depth researc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61K31/555A61P35/00
CPCC07F7/2284C07B2200/13
Inventor 蒋伍玖谭宇星张志坚朱小明邝代治张复兴庾江喜
Owner HENGYANG NORMAL UNIV
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