2-oxopropionic acid p-methoxybenzoyl hydrazone di(2,4-dichlorobenzyl) tin complex and preparation method and application thereof

A kind of technology of methoxybenzoyl hydrazone bis and methoxy benzoyl hydrazide, which is applied to 2-carbonyl propionic acid p-methoxy benzoyl hydrazone bis(2,4-dichlorobenzyl) tin complex The preparation and application fields thereof can solve the problems of undiscovered compounds and the like, and achieve the effects of simple preparation method, low cost and good anticancer activity

Inactive Publication Date: 2017-02-08
HENGYANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
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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-oxopropionic acid p-methoxybenzoyl hydrazone di(2,4-dichlorobenzyl) tin complex and preparation method and application thereof
  • 2-oxopropionic acid p-methoxybenzoyl hydrazone di(2,4-dichlorobenzyl) tin complex and preparation method and application thereof
  • 2-oxopropionic acid p-methoxybenzoyl hydrazone di(2,4-dichlorobenzyl) tin complex and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonylpropionic acid p-methoxybenzoylhydrazone bis(2,4-dichlorobenzyl)tin complex:

[0043] Add 0.510g (1.0mmol) bis(2,4-dichlorobenzyl) tin dichloride, 0.166g (1.0mmol) p-methoxybenzohydrazide, 0.115g ( 1.05mmol) of sodium pyruvate and 15mL of solvent anhydrous methanol, react at a temperature of 50~65°C for 8 h, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely For 2-carbonylpropionic acid p-methoxybenzoylhydrazone bis(2,4-dichlorobenzyl)tin complexes. Yield: 72.2%. Melting point: 103~105°C (dec).

[0044] Elemental analysis (C 52 h 48 Cl 8 N 4 o 10 sn 2 ): Calculated: C 44.29, H 3.43, N 3.97; Found: C 44.33, H 3.46, N 4.00.

[0045] FT-IR (KBr, ν / cm -1 ): 3447, 3060, 2957, 2932, 2838, 1675, 1601, 1580, 1470, 1385, 1250, 1169, 1023, 841, 726, 637, 591, 535, 506, 448.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.83 (d, J =9.0 Hz, 2H), 7.23 (d, J =2.0Hz, ...

Embodiment 2

[0051] Preparation of 2-carbonylpropionic acid p-methoxybenzoylhydrazone bis(2,4-dichlorobenzyl)tin complex:

[0052] Add 0.510g (1.0mmol) bis(2,4-dichlorobenzyl) tin dichloride, 0.174g (1.05mmol) p-methoxybenzohydrazide, 0.126g ( 1.15mmol) of sodium pyruvate and 35mL of solvent anhydrous methanol, react at a temperature of 50~65°C for 5 h, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely For 2-carbonylpropionic acid p-methoxybenzoylhydrazone bis(2,4-dichlorobenzyl)tin complexes. Yield: 75.0%. Melting point: 103~105°C (dec).

[0053] Elemental analysis (C 52 h 48 Cl 8 N 4 o 10 sn 2 ): Calculated: C 44.29, H 3.43, N 3.97; Found: C 44.33, H 3.46, N 4.00.

[0054] FT-IR (KBr, ν / cm -1 ): 3447, 3060, 2957, 2932, 2838, 1675, 1601, 1580, 1470, 1385, 1250, 1169, 1023, 841, 726, 637, 591, 535, 506, 448.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.83 (d, J =9.0 Hz, 2H), 7.23 (d, J =2.0Hz,...

Embodiment 3

[0060] Preparation of 2-carbonylpropionic acid p-methoxybenzoylhydrazone bis(2,4-dichlorobenzyl)tin complex:

[0061]Add 2.550g (5.0mmol) bis(2,4-dichlorobenzyl) tin dichloride, 0.847g (5.1mmol) p-methoxybenzohydrazide, 0.605g ( 5.5mmol) of sodium pyruvate and 25mL of solvent anhydrous methanol, reacted at a temperature of 50~65°C for 20 h, cooled, filtered, and controlled solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely For 2-carbonylpropionic acid p-methoxybenzoylhydrazone bis(2,4-dichlorobenzyl)tin complexes. Yield: 74.8%. Melting point: 103~105°C (dec).

[0062] Elemental analysis (C 52 h 48 Cl 8 N 4 o 10 sn 2 ): Calculated: C 44.29, H 3.43, N 3.97; Found: C 44.33, H 3.46, N 4.00.

[0063] FT-IR (KBr, ν / cm -1 ): 3447, 3060, 2957, 2932, 2838, 1675, 1601, 1580, 1470, 1385, 1250, 1169, 1023, 841, 726, 637, 591, 535, 506, 448.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.83 (d, J =9.0 Hz, 2H), 7.23 (d, J =2.0...

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Abstract

The invention discloses a 2-oxopropionic acid p-methoxybenzoyl hydrazone di(2,4-dichlorobenzyl) tin complex, which is a complex having the structural formula (I) as shown in the specification. In the structural formula (I), R is 2,4-dichlorobenzyl. The invention also discloses a preparation method of the 2-oxopropionic acid p-methoxybenzoyl hydrazone di(2,4-dichlorobenzyl) 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-carbonylpropionic acid p-methoxybenzoylhydrazone bis(2,4-dichlorobenzyl)tin complex and a preparation method thereof, and the 2-carbonylpropionic acid p-methoxybenzyl Application of acylhydrazone bis(2,4-dichlorobenzyl)tin complex 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 fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61K31/32A61K31/555A61P35/00
CPCC07F7/2284C07B2200/13C07F7/2296
Inventor 谭宇星蒋伍玖张志坚庾江喜张复兴邝代治朱小明
Owner HENGYANG NORMAL UNIV
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