2-carbonyl-3-phenylpropionic acid p-methyl benzoyl hydrazone bis-n-butyl tin complex and preparation method and application thereof

A technology of di-n-butyltin and di-n-butyltin oxide with toluylhydrazone, 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, The effect of high cancer activity and low cost

Active Publication Date: 2017-01-04
HENGYANG NORMAL UNIV
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  • 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 doe

Method used

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  • 2-carbonyl-3-phenylpropionic acid p-methyl benzoyl hydrazone bis-n-butyl tin complex and preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid p-methyl benzoyl hydrazone bis-n-butyl tin complex and preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid p-methyl benzoyl hydrazone bis-n-butyl tin complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0043] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.150g (1.0mmol) p-toluylhydrazide, 0.205g (1.1mmol) sodium phenylpyruvate and 15mL solvent in a 100mL three-necked flask protected by nitrogen Anhydrous methanol, react at 45~65°C for 8 hours, cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely 2-carbonyl-3-phenyl p-toluylhydrazone di-n-butyltin propionate complex. Yield: 85.5%. Melting point: 97~99°C (dec).

[0044] Elemental analysis (C 52 h 72 N 4 o 8 sn 2 ): Calculated: C 55.84, H 6.49, N 5.01; Found: C 55.90, H 6.45, N 5.00.

[0045] FT-IR (KBr, ν / cm -1 ): 3421, 3030, 2956, 2924, 2856, 1606, 1585, 1490, 1394, 1338, 1300, 1178, 1062, 1022, 918, 960, 837, 750, 707, 623, 588, 5455, 6.45

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.14 (d, J =8.1 Hz, 2H), 7.54 (d, J =7.0 Hz, 2H), 7.30...

Embodiment 2

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

[0052] Add 0.248g (1.0mmol) di-n-butyltin oxide, 0.150g (1.0mmol) p-toluylhydrazide, 0.195g (1.05mmol) sodium phenylpyruvate and 35mL solvent in a 100mL three-necked flask protected by nitrogen Anhydrous methanol, react for 5 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-carbonyl-3-phenyl p-toluylhydrazone di-n-butyltin propionate complex. Yield: 87.5%. Melting point: 97~99°C (dec).

[0053] Elemental analysis (C 52 h 72 N 4 o 8 sn 2 ): Calculated: C 55.84, H 6.49, N 5.01; Found: C 55.90, H 6.45, N 5.00.

[0054] FT-IR (KBr, ν / cm -1 ): 3421, 3030, 2956, 2924, 2856, 1606, 1585, 1490, 1394, 1338, 1300, 1178, 1062, 1022, 918, 960, 837, 750, 707, 623, 588, 5455, 6.45

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.14 (d, J =8.1 Hz...

Embodiment 3

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

[0061] Add 0.248g (1.0mmol) di-n-butyltin oxide, 0.158g (1.05mmol) p-toluylhydrazide, 0.214g (1.15mmol) sodium phenylpyruvate and 25mL solvent in a 100mL three-necked flask protected by nitrogen Anhydrous methanol, 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-carbonyl-3-phenyl p-toluylhydrazone di-n-butyltin propionate complex. Yield: 88.8%. Melting point: 97~99°C (dec).

[0062] Elemental analysis (C 52 h 72 N 4 o 8 sn 2 ): Calculated: C 55.84, H 6.49, N 5.01; Found: C 55.90, H 6.45, N 5.00.

[0063] FT-IR (KBr, ν / cm -1 ): 3421, 3030, 2956, 2924, 2856, 1606, 1585, 1490, 1394, 1338, 1300, 1178, 1062, 1022, 918, 960, 837, 750, 707, 623, 588, 5455, 6.45

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.14 (d, J =8.1 Hz...

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Abstract

The invention discloses a 2-carbonyl-3-phenylpropionic acid p-methyl benzoyl hydrazone bis-n-butyl tin complex. The complex has the structural formula (I) shown in the specification, wherein Ph is phenyl, and R is n-butyl. The invention further discloses a preparation method of the 2-carbonyl-3-phenylpropionic acid p-methyl benzoyl hydrazone bis-n-butyl tin complex and application in preparation of anti-cancer drugs.

Description

technical field [0001] The invention relates to a 2-carbonyl-3-phenylpropionic acid p-toluylhydrazone di-n-butyltin complex and a preparation method thereof, and the 2-carbonyl-3-phenylpropionic acid p-toluyl Application of hydrazone di-n-butyltin 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 found. They continued in-dep...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61K31/32A61K31/555A61P35/00
CPCC07B2200/13C07F7/2284C07F7/2296
Inventor 谭宇星蒋伍玖朱小明冯泳兰张复兴庾江喜邝代治
Owner HENGYANG NORMAL UNIV
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