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2-carbonyl-2-phenylacetic acid p-tert-butyl benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof

A technology of tert-butylbenzoylhydrazone di-n-butyltin and di-n-butyltin oxide is applied in the directions of tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve problems such as undiscovered compounds, and achieves simple preparation method, Good anticancer activity, low cost effect

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-2-phenylacetic acid p-tert-butyl benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof
  • 2-carbonyl-2-phenylacetic acid p-tert-butyl benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof
  • 2-carbonyl-2-phenylacetic acid p-tert-butyl 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-2-phenylacetic acid p-tert-butylbenzoylhydrazone di-n-butyltin complex:

[0043] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.192g (1.0mmol) p-tert-butylbenzohydrazide, 0.165g (1.1mmol) benzoylformic acid and 15mL The solvent is anhydrous methanol, react at a temperature of 45~65°C for 8 hours, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-benzene Di-n-butyltin complex of p-tert-butylbenzoylhydrazone glycolate. Yield: 85.6%. Melting point: 98~100°C (dec).

[0044] Elemental analysis (C 56 h 80 N 4 o 8 sn 2 ): Calculated: C 57.26, H 6.86, N 4.77; Found: C 57.30, H 6.88, N 4.77.

[0045] FT-IR (KBr, ν / cm -1 ): 3664, 3062, 2958, 2924, 2856, 1680, 1602, 1579, 1496, 1479, 1390, 1325, 1298, 1255, 1188, 1159, 1087, 1020, 821, 5, 713, 94 491, 472, 420.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.17-8.19 (m, 2H), 8.09 (d, J = 8.7Hz, 2H), 7...

Embodiment 2

[0051] Preparation of 2-carbonyl-2-phenylacetic acid p-tert-butylbenzoylhydrazone di-n-butyltin complex:

[0052] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.192g (1.0mmol) p-tert-butylbenzohydrazide, 0.157g (1.05mmol) benzoylformic acid and 35mL The solvent is anhydrous methanol, react at a temperature of 45~65°C for 5 hours, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-benzene Di-n-butyltin complex of p-tert-butylbenzoylhydrazone glycolate. Yield: 88.5%. Melting point: 98~100°C (dec).

[0053] Elemental analysis (C 56 h 80 N 4 o 8 sn 2 ): Calculated: C 57.26, H 6.86, N 4.77; Found: C 57.30, H 6.88, N 4.77.

[0054] FT-IR (KBr, ν / cm -1 ): 3664, 3062, 2958, 2924, 2856, 1680, 1602, 1579, 1496, 1479, 1390, 1325, 1298, 1255, 1188, 1159, 1087, 1020, 821, 5, 713, 94 491, 472, 420.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.17-8.19 (m, 2H), 8.09 (d, J = 8.7Hz, 2H), ...

Embodiment 3

[0060] Preparation of 2-carbonyl-2-phenylacetic acid p-tert-butylbenzoylhydrazone di-n-butyltin complex:

[0061] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.202g (1.05mmol) p-tert-butylbenzohydrazide, 0.173g (1.15mmol) benzoylformic acid and 25mL Solvent anhydrous methanol, react for 24 hours at a temperature of 45~65°C, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-benzene Di-n-butyltin complex of p-tert-butylbenzoylhydrazone glycolate. Yield: 88.0%. Melting point: 98~100°C (dec).

[0062] Elemental analysis (C 56 h 80 N 4 o 8 sn 2): Calculated: C 57.26, H 6.86, N 4.77; Found: C 57.30, H 6.88, N 4.77.

[0063] FT-IR (KBr, ν / cm -1 ): 3664, 3062, 2958, 2924, 2856, 1680, 1602, 1579, 1496, 1479, 1390, 1325, 1298, 1255, 1188, 1159, 1087, 1020, 821, 5, 713, 94 491, 472, 420.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.17-8.19 (m, 2H), 8.09 (d, J = 8.7Hz, 2H), 7.53-7...

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Abstract

The invention discloses a 2-carbonyl-2-phenylacetic acid p-tert-butyl benzoyl hydrazone di-n-butyltin complex. The 2-carbonyl-2-phenylacetic acid p-tert-butyl benzoyl hydrazone di-n-butyltin complex is the complex with the structural formula (I) shown in the specification, wherein Ph is phenyl, and R is normal-butyl. The invention further discloses a preparation method of the 2-carbonyl-2-phenylacetic acid p-tert-butyl benzoyl hydrazone di-n-butyltin complex and application in preparation of anti-cancer medicine.

Description

technical field [0001] The invention relates to a 2-carbonyl-2-phenylacetic acid p-tert-butylbenzoylhydrazone di-n-butyltin complex and a preparation method thereof, and the 2-carbonyl-2-phenylacetic acid p-tert-butylbenzoyl 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 ...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61K31/32A61K31/555A61P35/00
CPCC07B2200/13C07F7/2284C07F7/2296
Inventor 蒋伍玖谭宇星庾江喜朱小明张复兴邝代治
Owner HENGYANG NORMAL UNIV
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