2-carbonyl-3-phenylpropionic acid p-nitrobenzoyl hydrazone di-p-methyl benzyl tin complex as well as preparation method and application thereof

A kind of technology of nitrobenzoyl hydrazone di, methylbenzyl tin, applied in 2-carbonyl-3-phenylpropionic acid-p-nitrobenzoyl hydrazone di-p-methylbenzyl tin complex and preparation and Application field, can solve problems such as undiscovered compounds, and achieve the effects of simple preparation method, low cost and high 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 p-nitrobenzoyl hydrazone di-p-methyl benzyl tin complex as well as preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid p-nitrobenzoyl hydrazone di-p-methyl benzyl tin complex as well as preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic acid p-nitrobenzoyl hydrazone di-p-methyl benzyl tin 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 p-nitrobenzoylhydrazone di-p-methylbenzyltin complex:

[0043] Add 0.400g (1.0mmol) di-p-methylbenzyl tin dichloride, 0.181g (1.0mmol) p-nitrobenzohydrazide, 0.195g (1.05mmol) phenylpyruvate into a 100mL three-necked flask protected by nitrogen Sodium and 15mL of solvent, anhydrous methanol, reacted at a temperature of 50~65°C for 8 h, cooled, filtered, and controlled solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely 2-carbonyl- 3-Phenylpropanoic acid p-nitrobenzoylhydrazone di-p-methylbenzyltin complex. Yield: 70.6%. Melting point: 86~88°C (dec).

[0044] Elemental analysis (C 66 h 66 N 6 o 12 sn 2 ): Calculated: C 57.75, H 4.85, N 6.12; Found: C 57.80, H 4.84, N 6.11.

[0045] FT-IR (KBr, ν / cm -1 ): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525, 1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 5 815, 0, 51, 88, 71 459, 418.

[0046] 1 H NMR (5...

Embodiment 2

[0051] Preparation of 2-carbonyl-3-phenylpropionic acid p-nitrobenzoylhydrazone di-p-methylbenzyltin complex:

[0052] Add 0.400g (1.0mmol) di-p-methylbenzyl tin dichloride, 0.190g (1.05mmol) p-nitrobenzohydrazide, 0.214g (1.15mmol) phenylpyruvate into a 100mL three-necked flask protected by nitrogen Sodium and 35mL of solvent, anhydrous methanol, reacted for 5 hours at a temperature of 50~65°C, cooled, filtered, and controlled solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely 2-carbonyl- 3-Phenylpropanoic acid p-nitrobenzoylhydrazone di-p-methylbenzyltin complex. Yield: 73.3%. Melting point: 86~88°C (dec).

[0053] Elemental analysis (C 66 h 66 N 6 o 12 sn 2 ): Calculated: C 57.75, H 4.85, N 6.12; Found: C 57.80, H 4.84, N 6.11.

[0054] FT-IR (KBr, ν / cm -1 ): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525, 1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 5 815, 0, 51, 88, 71 459, 418.

[0055] 1 H N...

Embodiment 3

[0060] Preparation of 2-carbonyl-3-phenylpropionic acid p-nitrobenzoylhydrazone di-p-methylbenzyltin complex:

[0061] Add 2.000g (5.0mmol) di-p-methylbenzyl tin dichloride, 0.923g (5.1mmol) p-nitrobenzohydrazide, 1.023g (5.5mmol) phenylpyruvate into a 100mL three-necked flask protected by nitrogen Sodium and 25mL of solvent, anhydrous methanol, reacted at a temperature of 50~65°C for 20 h, cooled, filtered, and controlled solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely 2-carbonyl- 3-Phenylpropanoic acid p-nitrobenzoylhydrazone di-p-methylbenzyltin complex. Yield: 74.5%. Melting point: 86~88°C (dec).

[0062] Elemental analysis (C 66 h 66 N 6 o 12 sn 2 ): Calculated: C 57.75, H 4.85, N 6.12; Found: C 57.80, H 4.84, N 6.11.

[0063] FT-IR (KBr, ν / cm -1 ): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525, 1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 5 815, 0, 51, 88, 71 459, 418.

[0064] 1 H NMR (5...

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Abstract

The invention discloses a 2-carbonyl-3-phenylpropionic acid p-nitrobenzoyl hydrazone di-p-methyl benzyl tin complex of which the structural formula is shown in the description; in the formula, Ph is phenyl, and R is methyl benzyl. The invention further discloses a preparation method and application of the 2-carbonyl-3-phenylpropionic acid p-nitrobenzoyl hydrazone di-p-methyl benzyl tin complex in preparation of anti-cancer medicines.

Description

technical field [0001] The invention relates to a 2-carbonyl-3-phenylpropionic acid p-nitrobenzoylhydrazone di-p-methylbenzyltin complex and a preparation method thereof, and the 2-carbonyl-3-phenylpropionic acid p-nitrobenzoyl Application of benzoylhydrazone di-p-methylbenzyltin 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 w...

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邝代治张复兴庾江喜
Owner HENGYANG NORMAL UNIV
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