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2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone di-n-butyltin complex as well as preparation method and application thereof

A technology of di-n-butyltin phenylpropionate salicyloylhydrazone, di-n-butyltin oxide is applied in directions such as tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve problems such as undiscovered compounds, and achieves simple preparation method and low cost Effect of low, good anticancer activity

Active Publication Date: 2016-12-14
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-3-phenylpropionic acid salicyloyl hydrazone di-n-butyltin complex as well as preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone di-n-butyltin complex as well as preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone di-n-butyltin complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonyl-3-phenylpropionic acid salicylhydrazone di-n-butyltin complex:

[0043] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.152g (1.0mmol) salicylic hydrazide, 0.205g (1.1mmol) sodium phenylpyruvate and 15mL solvent anhydrous methanol in a 100mL three-necked flask protected by nitrogen. 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-3-phenylpropionic acid salicylhydrazone di n-Butyltin complexes. Yield: 83.3%. Melting point: 164~166°C (dec).

[0044] Elemental analysis (C 24 h 30 N 2 o 4 Sn): Calculated: C 54.47, H 5.71, N 5.29; Found: C 54.50, H 5.70, N 5.26.

[0045] FT-IR (KBr, ν / cm -1 ): 3450, 3059, 2960, 2926, 2860, 1616, 1598, 1510, 1490, 1452, 1381, 1323, 1174, 858, 754, 713, 682, 632, 586, 511, 428.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 11.72 (s, 1H), 7.99~8.01 (d, J =7.9Hz, 1H), 7.4...

Embodiment 2

[0051] Preparation of 2-carbonyl-3-phenylpropionic acid salicylhydrazone di-n-butyltin complex:

[0052] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.152g (1.0mmol) salicylhydrazide, 0.195g (1.05mmol) sodium phenylpyruvate and 35mL solvent anhydrous methanol in a 100mL three-necked flask protected by nitrogen. React at a temperature of 45-65°C for 5 hours, cool, filter, and control solvent volatilization and crystallization at a temperature of 20-35°C to obtain a yellow transparent crystal, which is 2-carbonyl-3-phenylpropionic acid salicylhydrazone di n-Butyltin complexes. Yield: 85.5%. Melting point: 164~166°C (dec).

[0053] Elemental analysis (C 24 h 30 N 2 o 4 Sn): Calculated: C 54.47, H 5.71, N 5.29; Found: C 54.50, H 5.70, N 5.26.

[0054] FT-IR (KBr, ν / cm -1 ): 3450, 3059, 2960, 2926, 2860, 1616, 1598, 1510, 1490, 1452, 1381, 1323, 1174, 858, 754, 713, 682, 632, 586, 511, 428.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 11.72 (s, 1H), 7.99~8.01 (d, J =7.9H...

Embodiment 3

[0060] Preparation of 2-carbonyl-3-phenylpropionic acid salicylhydrazone di-n-butyltin complex:

[0061] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.160g (1.05mmol) salicylhydrazide, 0.214g (1.15mmol) sodium phenylpyruvate and 25mL solvent anhydrous methanol in a 100mL three-necked flask protected by nitrogen. React at a temperature of 45-65°C for 24 hours, cool, filter, and control solvent volatilization and crystallization at a temperature of 20-35°C to obtain a yellow transparent crystal, which is 2-carbonyl-3-phenylpropionic acid salicylhydrazone di n-Butyltin complexes. Yield: 84.1%. Melting point: 164~166°C (dec).

[0062] Elemental analysis (C 24 h 30 N 2 o 4 Sn): Calculated: C 54.47, H 5.71, N 5.29; Found: C 54.50, H 5.70, N 5.26.

[0063] FT-IR (KBr, ν / cm -1): 3450, 3059, 2960, 2926, 2860, 1616, 1598, 1510, 1490, 1452, 1381, 1323, 1174, 858, 754, 713, 682, 632, 586, 511, 428.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 11.72 (s, 1H), 7.99~8.01 (d, J =7.9...

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Abstract

The invention discloses a 2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone di-n-butyltin complex of which the structural formula is as shown in the specification; in the formula, Ph is phenyl, and R is n-butyl. The invention further discloses a preparation method and application of the 2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone di-n-butyltin complex in preparation of anti-cancer medicines.

Description

technical field [0001] The invention relates to a 2-carbonyl-3-phenylpropionic acid salicylhydrazone di-n-butyltin complex and a preparation method thereof, and the 2-carbonyl-3-phenylpropionic acid salicylhydrazone di-n-butyltin complex is used in the preparation of anticancer application in medicine. 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 continue...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61K31/32A61K31/555A61P35/00
CPCC07B2200/13C07F7/2284C07F7/2296
Inventor 谭宇星蒋伍玖张复兴邝代治朱小明庾江喜
Owner HENGYANG NORMAL UNIV
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