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

A technology of benzoylhydrazone di-n-butyltin phenylpropionate and complexes, which is applied in the fields of tin organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve the problems of undiscovered compounds, etc., and achieve simple preparation methods, high resistance High cancer activity and good anticancer activity

Active Publication Date: 2017-01-04
HENGYANG NORMAL UNIV
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  • 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 benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0043] Add 0.248g (1.0mmol) dibutyltin oxide, 0.136g (1.0mmol) benzohydrazide, 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 solvent volatilization and crystallization at a temperature of 20-35°C to obtain a yellow transparent crystal, which is 2-carbonyl-3-phenylpropionic acid benzyl Acylhydrazone di-n-butyltin complexes. Yield: 77.6%. Melting point: 91~93°C (dec).

[0044] Elemental analysis (C 50 h 68 N 4 o 8 sn 2 ): Calculated: C 55.07, H 6.29, N 5.14; Found: C 55.14, H 6.24, N 5.19.

[0045] FT-IR (KBr, ν / cm -1 ): 3446, 3084, 3028, 2956, 2924, 2856, 1616, 1589, 1579, 1492, 1388, 1344, 1172, 1074, 860, 754, 711, 698, 630, 586, 551, 7.491,

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.26 (d, J =7.5 Hz, 2H), 7.49...

Embodiment 2

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

[0052] Add 0.248g (1.0mmol) dibutyltin oxide, 0.136g (1.0mmol) benzohydrazide, 0.195g (1.05mmol) sodium phenylpyruvate and 35mL solvent anhydrous methanol in a 100mL three-necked flask protected by nitrogen, React for 5 hours at a temperature of 45~65°C, cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-3-phenylpropionic acid benzyl Acylhydrazone di-n-butyltin complexes. Yield: 78.5%. Melting point: 91~93°C (dec).

[0053] Elemental analysis (C 50 h 68 N 4 o 8 sn 2 ): Calculated: C 55.07, H 6.29, N 5.14; Found: C 55.14, H 6.24, N 5.19.

[0054] FT-IR (KBr, ν / cm -1 ): 3446, 3084, 3028, 2956, 2924, 2856, 1616, 1589, 1579, 1492, 1388, 1344, 1172, 1074, 860, 754, 711, 698, 630, 586, 551, 7.491,

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.26 (d, J =7.5 Hz, 2H), 7.49~7.60 (m,5H), 7....

Embodiment 3

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

[0061] Add 0.248g (1.0mmol) dibutyltin oxide, 0.143g (1.05mmol) benzohydrazide, 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 the solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-3-phenylpropionic acid benzyl Acylhydrazone di-n-butyltin complexes. Yield: 76.0%. Melting point: 91~93°C (dec).

[0062] Elemental analysis (C 50 h 68 N 4 o 8 sn 2 ): Calculated: C 55.07, H 6.29, N 5.14; Found: C 55.14, H 6.24, N 5.19.

[0063] FT-IR (KBr, ν / cm -1 ): 3446, 3084, 3028, 2956, 2924, 2856, 1616, 1589, 1579, 1492, 1388, 1344, 1172, 1074, 860, 754, 711, 698, 630, 586, 551, 7.491,

[0064] 1 H NMR (500 MHz, CDCl3 , δ / ppm): 8.26 (d, J =7.5 Hz, 2H),...

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Abstract

The invention discloses a 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone di-n-butyltin complex. The 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone di-n-butyltin complex is a complex with the structural formula (I) (please see the formula (I) in the description), wherein Ph is phenyl, and R is n-butyl. The invention further discloses a preparation method of the 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone di-n-butyltin complex and application of the 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone di-n-butyltin complex to anti-cancer drug preparation.

Description

technical field [0001] The invention relates to a 2-carbonyl-3-phenylpropionic acid benzoylhydrazone di-n-butyltin complex and a preparation method thereof, and the 2-carbonyl-3-phenylpropionic acid benzoylhydrazone di-n-butyltin 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 res...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61K31/32A61P35/00
CPCC07B2200/13C07F7/2284
Inventor 谭宇星蒋伍玖朱小明张复兴邝代治庾江喜
Owner HENGYANG NORMAL UNIV
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