2-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl tin complex, and preparation method and application thereof

A kind of technology of tert-butylbenzoylhydrazone dibenzyltin and phenylpropionic acid, applied to 2-carbonyl-3-phenylpropionic acid p-tert-butylbenzoylhydrazone dibenzyltin complex and preparation thereof It can solve the problems of undiscovered compounds and other problems, and achieve the effects of simple preparation method, high anti-cancer activity and good anti-cancer 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-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl tin complex, and preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl tin complex, and preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl 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-tert-butylbenzoylhydrazone dibenzyltin complex:

[0043] Add 0.372g (1.0mmol) dibenzyl tin dichloride, 0.192g (1.0mmol) p-tert-butylbenzohydrazide, 0.195g (1.05mmol) sodium phenylpyruvate and 15mL of anhydrous methanol as a solvent, react for 8 hours at a temperature of 50~65°C, 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 dibenzyltin complex with p-tert-butylbenzoylhydrazone. Yield: 80.6%. Melting point: 115~117°C (dec).

[0044] Elemental analysis (C 70 h 76 N 4 o 8 sn 2 ): Calculated: C 62.80, H 5.72, N 4.18; Found: C 62.86, H 5.70, N 4.17.

[0045] FT-IR (KBr, ν / cm -1 ): 3446, 3057, 3026, 2962, 1610, 1598, 1490, 1454, 1392, 1332, 1298, 1190, 1166, 1016, 893, 852, 756, 711, 696, 634, 594, 5445, 35, 408.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.99 (d, J =8.5 Hz...

Embodiment 2

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

[0052] Add 0.372g (1.0mmol) dibenzyltin dichloride, 0.202g (1.05mmol) p-tert-butylbenzohydrazide, 0.214g (1.15mmol) sodium phenylpyruvate and 35mL of anhydrous methanol as a solvent, react for 5 hours at a temperature of 50~65°C, 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 dibenzyltin complex with p-tert-butylbenzoylhydrazone. Yield: 82.5%. Melting point: 115~117°C (dec).

[0053] Elemental analysis (C 70 h 76 N 4 o 8 sn 2 ): Calculated: C 62.80, H 5.72, N 4.18; Found: C 62.86, H 5.70, N 4.17.

[0054] FT-IR (KBr, ν / cm -1 ): 3446, 3057, 3026, 2962, 1610, 1598, 1490, 1454, 1392, 1332, 1298, 1190, 1166, 1016, 893, 852, 756, 711, 696, 634, 594, 5445, 35, 408.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.99 (d, J =8.5 Hz...

Embodiment 3

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

[0061] Add 1.860g (5.0mmol) dibenzyltin dichloride, 0.979g (5.1mmol) p-tert-butylbenzohydrazide, 1.023g (5.5mmol) sodium phenylpyruvate and 25mL solvent anhydrous methanol, react at a temperature of 50~65°C for 20 h, 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 dibenzyltin complex with p-tert-butylbenzoylhydrazone. Yield: 82.8%. Melting point: 115~117°C (dec).

[0062] Elemental analysis (C 70 h 76 N 4 o 8 sn 2 ): Calculated: C 62.80, H 5.72, N 4.18; Found: C 62.86, H 5.70, N 4.17.

[0063]FT-IR (KBr, ν / cm -1 ): 3446, 3057, 3026, 2962, 1610, 1598, 1490, 1454, 1392, 1332, 1298, 1190, 1166, 1016, 893, 852, 756, 711, 696, 634, 594, 5445, 35, 408.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 7.99 (d, J =8.5 Hz, 2H), 7.50 (d...

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Abstract

The invention discloses a 2-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl tin complex which is represented as the structure formula (I), wherein Ph refers to phenyl group and R refers to benzyl group, and the invention also discloses a preparation method of the 2-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl tin complex, and applications of the compound in preparation of anticancer medicines.

Description

technical field [0001] The invention relates to a 2-carbonyl-3-phenylpropionic acid p-tert-butylbenzoylhydrazone dibenzyltin complex and a preparation method thereof, and the 2-carbonyl-3-phenylpropionic acid p-tert-butyl Application of benzoylhydrazone 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. 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. The...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00
CPCC07F7/2284
Inventor 蒋伍玖谭宇星庾江喜邝代治张复兴朱小明冯泳兰
Owner HENGYANG NORMAL UNIV
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