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2-carbonyl-2-phenyl acetic acid para methoxyphenyl carbonylhydrazone di-n-butyl tin complex and preparation method and application thereof

A technology of methoxybenzoylhydrazone di-n-butyltin and di-n-butyltin oxide, which is applied in the fields of tin organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve the problems of undiscovered compounds and achieve the preparation method Simple, high anticancer activity, low cost effect

Active 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-2-phenyl acetic acid para methoxyphenyl carbonylhydrazone di-n-butyl tin complex and preparation method and application thereof
  • 2-carbonyl-2-phenyl acetic acid para methoxyphenyl carbonylhydrazone di-n-butyl tin complex and preparation method and application thereof
  • 2-carbonyl-2-phenyl acetic acid para methoxyphenyl carbonylhydrazone di-n-butyl tin 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-methoxybenzoylhydrazone di-n-butyltin complex:

[0043] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.166g (1.0mmol) p-methoxybenzohydrazide, 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 p-methoxybenzoylhydrazone di-n-butyltin complex. Yield: 75.6%. Melting point: 98~100°C (dec).

[0044] Elemental analysis (C 50 h 68 N 4 o 10 sn 2 ): Calculated: C 53.50, H 6.11, N 4.99; Found: C 53.57, H 6.13, N 4.97.

[0045] FT-IR (KBr, ν / cm -1 ): 3454, 3057, 2956, 2924, 2870, 1678, 1602, 1587, 1494, 1477, 1388, 1325, 1249, 1170, 1089, 823, 756, 688, 617, 597, 504, 514, 2.4

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.16-8.18 (m, 2H), 8.11 (d, J = 9.0Hz, 2H), 7.53-7.56 (m, 3H), 6.94 (d, J =...

Embodiment 2

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

[0052] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.166g (1.0mmol) p-methoxybenzohydrazide, 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 p-methoxybenzoylhydrazone di-n-butyltin complex. Yield: 77.5%. Melting point: 98~100°C (dec).

[0053] Elemental analysis (C 50 h 68 N 4 o 10 sn 2 ): Calculated: C 53.50, H 6.11, N 4.99; Found: C 53.57, H 6.13, N 4.97.

[0054] FT-IR (KBr, ν / cm -1 ): 3454, 3057, 2956, 2924, 2870, 1678, 1602, 1587, 1494, 1477, 1388, 1325, 1249, 1170, 1089, 823, 756, 688, 617, 597, 504, 514, 2.4

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.16-8.18 (m, 2H), 8.11 (d, J = 9.0Hz, 2H), 7.53-7.56 (m, 3H), 6.94 (d, J ...

Embodiment 3

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

[0061] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.174g (1.05mmol) p-methoxybenzohydrazide, 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 p-methoxybenzoylhydrazone di-n-butyltin complex. Yield: 73.0%. Melting point: 98~100°C (dec).

[0062] Elemental analysis (C 50 h 68 N 4 o 10 sn 2): Calculated: C 53.50, H 6.11, N 4.99; Found: C 53.57, H 6.13, N 4.97.

[0063] FT-IR (KBr, ν / cm -1 ): 3454, 3057, 2956, 2924, 2870, 1678, 1602, 1587, 1494, 1477, 1388, 1325, 1249, 1170, 1089, 823, 756, 688, 617, 597, 504, 514, 2.4

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.16-8.18 (m, 2H), 8.11 (d, J = 9.0Hz, 2H), 7.53-7.56 (m, 3H), 6.94 (d, J = 9.0 ...

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Abstract

The invention discloses a 2-carbonyl-2-phenyl acetic acid para methoxyphenyl carbonylhydrazone di-n-butyl tin complex. The complex has a structural formula (I) shown in the specification, wherein Ph is phenyl, and R is n-butyl. The invention further discloses a preparation method of the 2-carbonyl-2-phenyl acetic acid para methoxyphenyl carbonylhydrazone di-n-butyl tin complex and application in preparation of anti-cancer medicine.

Description

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

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61P35/00
CPCC07B2200/13C07F7/2284
Inventor 蒋伍玖谭宇星张志坚朱小明庾江喜张复兴邝代治
Owner HENGYANG NORMAL UNIV
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