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2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin complex, and preparation method and application thereof

A kind of technology of methylbenzoylhydrazone dibenzyltin and phenylpropionic acid, applied in 2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone dibenzyltin complex and preparation and application thereof It can solve the problems of undiscovered compounds and other problems, and achieve the effects of simple preparation method, low cost and good anticancer activity

Inactive Publication Date: 2017-02-01
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-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin complex, and preparation method and application thereof
  • 2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin complex, and preparation method and application thereof
  • 2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin 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 dibenzyltin complex:

[0043] Add 0.372g (1.0mmol) dibenzyltin dichloride, 0.150g (1.0mmol) p-toluic hydrazide, 0.195g (1.05mmol) sodium phenylpyruvate and 15mL in a 100mL three-necked flask with nitrogen protection Solvent anhydrous methanol, react for 8 h at a temperature of 50~65℃, cool, filter, and control the solvent to volatilize and crystallize at 20~35℃ to obtain yellow transparent crystals, namely 2-carbonyl-3-benzene 4-methylbenzoyl hydrazone dibenzyl tin complex with propyl propionate. Yield: 75.6%. Melting point: 115~117°C (dec).

[0044] Elemental Analysis (C 64 H 64 N 4 O 8 Sn 2 ): Calculated value: C 61.27, H 5.14, N 4.47; measured value: C 61.30, H5.12, N 4.40.

[0045] FT-IR (KBr, ν / cm -1 ): 3446, 3059, 3024, 2935, 1610, 1597, 1490, 1452,1392, 1336, 1298, 1174, 1134, 1226, 893, 835, 746, 713, 696, 642, 592, 553,513, 459, 418.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.95 (d, J =7.7...

Embodiment 2

[0051] Preparation of 2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone dibenzyltin complex:

[0052] Add 0.372g (1.0mmol) dibenzyltin dichloride, 0.158g (1.05mmol) p-toluic hydrazide, 0.214g (1.15mmol) sodium phenylpyruvate and 35mL in a 100mL three-necked flask with nitrogen protection Solvent anhydrous methanol, react for 5 h at a temperature of 50-65°C, cool, filter, and control the solvent to volatilize and crystallize at a temperature of 20-35°C to obtain yellow transparent crystals, namely 2-carbonyl-3-benzene P-methylbenzoyl hydrazone dibenzyl tin complex. Yield: 77.5%. Melting point: 115~117°C (dec).

[0053] Elemental Analysis (C 64 H 64 N 4 O 8 Sn 2 ): Calculated value: C 61.27, H 5.14, N 4.47; measured value: C 61.30, H5.12, N 4.40.

[0054] FT-IR (KBr, ν / cm -1 ): 3446, 3059, 3024, 2935, 1610, 1597, 1490, 1452,1392, 1336, 1298, 1174, 1134, 1226, 893, 835, 746, 713, 696, 642, 592, 553,513, 459, 418.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.95 (d, J =7.7 Hz...

Embodiment 3

[0060] Preparation of 2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone dibenzyltin complex:

[0061] Add 1.860g (5.0mmol) dibenzyltin dichloride, 0.765g (5.1mmol) p-toluic hydrazide, 1.023g (5.5mmol) sodium phenylpyruvate and 25mL in a 100mL three-necked flask with nitrogen protection Solvent anhydrous methanol, react for 20 h at a temperature of 50-65°C, cool, filter, and control the solvent to volatilize and crystallize at a temperature of 20-35°C to obtain yellow transparent crystals, namely 2-carbonyl-3-benzene 4-methylbenzoyl hydrazone dibenzyl tin complex with propyl propionate. Yield: 77.8%. Melting point: 115~117°C (dec).

[0062] Elemental Analysis (C 64 H 64 N 4 O 8 Sn 2 ): Calculated value: C 61.27, H 5.14, N 4.47; measured value: C 61.30, H5.12, N 4.40.

[0063] FT-IR (KBr, ν / cm -1 ): 3446, 3059, 3024, 2935, 1610, 1597, 1490, 1452,1392, 1336, 1298, 1174, 1134, 1226, 893, 835, 746, 713, 696, 642, 592, 553,513, 459, 418.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm...

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Abstract

The invention discloses a 2-oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin complex. The complex is represented by structural formula (I); and in the structural formula (I), Ph is a phenyl group, and R is a benzyl group. The invention also discloses a preparation method of the 2-oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin complex, and an application of the complex in the preparation of anticancer medicines.

Description

Technical field [0001] The invention relates to a 2-carbonyl-3-phenylpropionic acid p-methylbenzoylhydrazone dibenzyltin complex and a preparation method thereof, and the 2-carbonyl-3-phenylpropionic acid p-methylbenzyl Application of acylhydrazone dibenzyltin 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. The anti-tumor activity of organotin (IV) compounds can be traced back to 1929. In 1967, Kanisawa et al. believed that tin chloride was not effective on primary tumors in mice and rats. But in 1972, Brown discovered that by food or injection, triphenyltin acetate Ph 3 SnOOCCH 3 It can inhibit tumor growth in mice, while triphenyltin chloride cannot. From 1972 to 1977, Dutch scholars studied a large number of organotin compounds, but no compounds with further screening value were found...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61P35/00
CPCC07F7/2284
Inventor 谭宇星蒋伍玖冯泳兰邝代治庾江喜张复兴朱小明
Owner HENGYANG NORMAL UNIV
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