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2-carbonyl-2-phenyl acetic acid p-methoxy-benzoyl hydrazone diphenyltin complex and preparing method and application thereof

A kind of technology of methoxybenzoylhydrazone diphenyltin and phenylacetic acid, applied in 2-carbonyl-2-phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex and preparation and application thereof It can solve the problems of undiscovered compounds, etc., and achieve the effect of simple preparation method, low cost and good anticancer activity

Inactive Publication Date: 2017-01-25
HENGYANG NORMAL UNIV
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  • 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-phenyl acetic acid p-methoxy-benzoyl hydrazone diphenyltin complex and preparing method and application thereof
  • 2-carbonyl-2-phenyl acetic acid p-methoxy-benzoyl hydrazone diphenyltin complex and preparing method and application thereof
  • 2-carbonyl-2-phenyl acetic acid p-methoxy-benzoyl hydrazone diphenyltin complex and preparing method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonyl-2-phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex:

[0043] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.166g (1.0mmol) p-methoxybenzohydrazide, 0.165g (1.1mmol) benzoylformic acid and 15mL of anhydrous methanol as a solvent, react for 8 hours at a temperature of 45~65°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-2- Phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex. Yield: 77.6%. Melting point: 262~264°C (dec).

[0044] Elemental analysis (C 112 h 88 N 8 o 16 sn 4 ): Calculated: C 59.08, H 3.90, N 4.92; Found: C 59.13, H 3.93, N 4.97.

[0045] FT-IR (KBr, ν / cm -1 ): 3616, 3051, 2995, 2935, 2839, 1689, 1602, 1562, 1492, 1473, 1386, 1249, 1170, 1087, 1024, 819, 729, 694, 644, 619, 594, 516,

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.26 (d, J = 9.0 Hz, 2H), 8.17-8.19(m, 2H), 7.86-7....

Embodiment 2

[0051] Preparation of 2-carbonyl-2-phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex:

[0052] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.166g (1.0mmol) p-methoxybenzohydrazide, 0.157g (1.05mmol) benzoylformic acid and 35mL of anhydrous methanol as a solvent, react for 5 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- Phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex. Yield: 77.8%. Melting point: 262~264°C (dec).

[0053] Elemental analysis (C 112 h 88 N 8 o 16 sn 4 ): Calculated: C 59.08, H 3.90, N 4.92; Found: C 59.13, H 3.93, N 4.97.

[0054] FT-IR (KBr, ν / cm -1 ): 3616, 3051, 2995, 2935, 2839, 1689, 1602, 1562, 1492, 1473, 1386, 1249, 1170, 1087, 1024, 819, 729, 694, 644, 619, 594, 516,

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.26 (d, J = 9.0 Hz, 2H), 8.17-8.19(m, 2H), 7.86-7.88 (m, 4H), 7.47...

Embodiment 3

[0060] Preparation of 2-carbonyl-2-phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex:

[0061] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.174g (1.05mmol) p-methoxybenzohydrazide, 0.173g (1.15mmol) benzoylformic acid and 25mL of anhydrous methanol as a solvent, react for 24 hours at a temperature of 45~65°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-2- Phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex. Yield: 76.0%. Melting point: 262~264°C (dec).

[0062] Elemental analysis (C 112 h 88 N 8 o 16 sn 4 ): Calculated: C 59.08, H 3.90, N 4.92; Found: C 59.13, H 3.93, N 4.97.

[0063] FT-IR (KBr, ν / cm -1 ): 3616, 3051, 2995, 2935, 2839, 1689, 1602, 1562, 1492, 1473, 1386, 1249, 1170, 1087, 1024, 819, 729, 694, 644, 619, 594, 516,

[0064] 1 H NMR (500 MHz, CDCl3 , δ / ppm): 8.26 (d, J = 9.0 Hz, 2H), 8.17-8.19(m, 2H), 7.86-7...

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Abstract

The invention discloses a 2-carbonyl-2-phenyl acetic acid p-methoxy-benzoyl hydrazone diphenyltin complex, which is a complex of the following structural formula (I) (img file='dest_path_image002.TIF' wi='357' he='279' / ), wherein Ph is phenyl. The invention further discloses the preparing method and application thereof in the preparation of anticancer drugs.

Description

technical field [0001] The invention relates to a 2-carbonyl-2-phenylacetic acid p-methoxybenzoylhydrazone diphenyltin complex and a preparation method thereof, and the 2-carbonyl-2-phenylacetic acid p-methoxybenzyl Application of the acylhydrazone diphenyltin 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 con...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61K31/32A61K31/555A61P35/00
CPCC07F7/2284C07B2200/13C07F7/2296
Inventor 蒋伍玖谭宇星张志坚邝代治朱小明庾江喜张复兴
Owner HENGYANG NORMAL UNIV
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