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2-carbonl-2-phenyl acetic acid p-methyl benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof

A technology of di-n-butyltin and di-n-butyltin oxide with toluylhydrazone, which is applied in the fields of tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve the problems of undiscovered compounds and achieve simple preparation methods, High cancer activity and good anticancer activity

Active Publication Date: 2016-12-14
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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-carbonl-2-phenyl acetic acid p-methyl benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof
  • 2-carbonl-2-phenyl acetic acid p-methyl benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof
  • 2-carbonl-2-phenyl acetic acid p-methyl 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-toluylhydrazone di-n-butyltin complex:

[0043] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.150g (1.0mmol) p-toluylhydrazide, 0.165g (1.1mmol) benzoylformic acid and 15mL solvent into a 100mL three-necked flask protected by nitrogen Anhydrous methanol, react at a temperature of 45~65°C for 8 hours, cool, filter, and control solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-phenyl p-Tolylhydrazone di-n-butyltin acetate complex. Yield: 79.6%. Melting point: 98~100°C (dec).

[0044] Elemental analysis (C 50 h 68 N 4 o 8 sn 2 ): Calculated: C 55.07, H 6.29, N 5.14; Found: C 55.09, H 6.24, N 5.19.

[0045] FT-IR (KBr, ν / cm -1 ): 3462, 3059, 2956, 2924, 2856, 1680, 1595, 1581, 1494, 1477, 1388, 1321, 1296, 1251, 1178, 1085, 1022, 823, 750, 5 223, 7, 96, 638 487, 468, 422.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.17-8.19 (m, 2H), ...

Embodiment 2

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

[0052] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.150g (1.0mmol) p-toluylhydrazide, 0.157g (1.05mmol) benzoylformic acid and 35mL solvent into a 100mL three-necked flask protected by nitrogen Anhydrous methanol, react for 5 hours at a temperature of 45~65°C, cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-phenyl p-Tolylhydrazone di-n-butyltin acetate complex. Yield: 82.5%. Melting point: 98~100°C (dec).

[0053] Elemental analysis (C 50 h 68 N 4 o 8 sn 2 ): Calculated: C 55.07, H 6.29, N 5.14; Found: C 55.09, H 6.24, N 5.19.

[0054] FT-IR (KBr, ν / cm -1 ): 3462, 3059, 2956, 2924, 2856, 1680, 1595, 1581, 1494, 1477, 1388, 1321, 1296, 1251, 1178, 1085, 1022, 823, 750, 5 223, 7, 96, 638 487, 468, 422.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.17-8.19 (m, 2H), 8.04 (d, J = 8...

Embodiment 3

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

[0061] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.157g (1.05mmol) p-toluylhydrazide, 0.173g (1.15mmol) benzoylformic acid and 25mL solvent into a 100mL three-necked flask protected by nitrogen Anhydrous methanol, react for 24 hours at a temperature of 45~65°C, cool, filter, and control solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-phenyl p-Tolylhydrazone di-n-butyltin acetate complex. Yield: 81.0%. Melting point: 98~100°C (dec).

[0062] Elemental analysis (C 50 h 68 N 4 o 8 sn 2 ): Calculated: C 55.07, H 6.29, N 5.14; Found: C 55.09, H 6.24, N 5.19.

[0063] FT-IR (KBr, ν / cm -1 ): 3462, 3059, 2956, 2924, 2856, 1680, 1595, 1581, 1494, 1477, 1388, 1321, 1296, 1251, 1178, 1085, 1022, 823, 750, 5 223, 7, 96, 638 487, 468, 422.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.17-8.19 (m, 2H),...

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Abstract

The invention discloses a 2-carbonl-2-phenyl acetic acid p-methyl benzoyl hydrazone di-n-butyltin complex. As is shown in the formula I, Ph is phenyl and R is n-butyl. The invention further discloses a preparation method of the 2-carbonl-2-phenyl acetic acid p-methyl benzoyl hydrazone di-n-butyltin complex and an application of the 2-carbonl-2-phenyl acetic acid p-methyl benzoyl hydrazone di-n-butyltin complex in preparation of anti-cancer drugs.

Description

technical field [0001] The invention relates to a 2-carbonyl-2-phenylacetic acid p-toluylhydrazone di-n-butyltin complex and a preparation method thereof, and the 2-carbonyl-2-phenylacetic acid p-toluylhydrazone di-n-butyltin complex Application of n-butyltin complexes 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 co...

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张复兴邝代治朱小明
Owner HENGYANG NORMAL UNIV
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