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2-oxobutyrate p-toluyl hydrazone di-n-butyltin complex as well as preparation method and application thereof

A technology of di-n-butyltin and di-n-butyltin oxide with toluylhydrazone, which is applied in tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve problems such as undiscovered compounds, and achieve simple preparation methods, The effect of high cancer activity and low cost

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-oxobutyrate p-toluyl hydrazone di-n-butyltin complex as well as preparation method and application thereof
  • 2-oxobutyrate p-toluyl hydrazone di-n-butyltin complex as well as preparation method and application thereof
  • 2-oxobutyrate p-toluyl hydrazone di-n-butyltin complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonylbutanoic acid p-methylbenzoylhydrazone di-n-butyltin complex:

[0043] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.150g (1.0mmol) p-toluylhydrazide, 0.112g (1.1mmol) 2-butanuonic acid and 15mL The solvent is anhydrous methanol, and reacted at a temperature of 45~65°C for 8 hours, cooled, filtered, and controlled to volatilize and crystallize the solvent at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonylbutyric acid p-formaldehyde Di-n-butyltin complexes of benzoylhydrazone. Yield: 84.9%. Melting point: 86~88°C (dec).

[0044] Elemental analysis (C 42 h 68 N 4 o 8 sn 2 ): Calculated: C 50.73, H 6.89, N 5.63; Found: C 50.79, H 6.90, N 5.65.

[0045] FT-IR (KBr, ν / cm -1 ): 3527, 2960, 2922, 2858, 1608, 1581, 1487, 1460, 1390, 1334, 1296, 1261, 1193, 1176, 1155, 1058, 837, 862, 707, 684, 626, 8, 603 464, 443.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.09 (d, J =8.2 Hz, 2H), 7.27 (s, 1H),7.26 (s, 1H), 3.48 (s, 3...

Embodiment 2

[0051] Preparation of 2-carbonylbutanoic acid p-methylbenzoylhydrazone di-n-butyltin complex:

[0052] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.150g (1.0mmol) p-toluylhydrazide, 0.107g (1.05mmol) 2-butanuonic acid and 35mL The solvent is anhydrous methanol, reacted for 5 hours at a temperature of 45~65°C, cooled, filtered, and controlled solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonylbutyric acid p-methyl Di-n-butyltin complexes of benzoylhydrazone. Yield: 85.5%. Melting point: 86~88°C (dec).

[0053] Elemental analysis (C 42 h 68 N 4 o 8 sn 2 ): Calculated: C 50.73, H 6.89, N 5.63; Found: C 50.79, H 6.90, N 5.65.

[0054] FT-IR (KBr, ν / cm -1 ): 3527, 2960, 2922, 2858, 1608, 1581, 1487, 1460, 1390, 1334, 1296, 1261, 1193, 1176, 1155, 1058, 837, 862, 707, 684, 626, 8, 603 464, 443.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.09 (d, J =8.2 Hz, 2H), 7.27 (s, 1H),7.26 (s, 1H), 3...

Embodiment 3

[0060] Preparation of 2-carbonylbutanoic acid p-methylbenzoylhydrazone di-n-butyltin complex:

[0061] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.157g (1.05mmol) p-toluylhydrazide, 0.117g (1.15mmol) 2-butanuonic acid and 25mL The solvent is anhydrous methanol, reacted for 24 hours at a temperature of 45~65°C, cooled, filtered, and controlled solvent volatilization and crystallization at a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonylbutyric acid p-methyl Di-n-butyltin complexes of benzoylhydrazone. Yield: 84.6%. Melting point: 86~88°C (dec).

[0062] Elemental analysis (C 42 h 68 N 4 o 8 sn 2 ): Calculated: C 50.73, H 6.89, N 5.63; Found: C 50.79, H 6.90, N 5.65.

[0063] FT-IR (KBr, ν / cm -1 ): 3527, 2960, 2922, 2858, 1608, 1581, 1487, 1460, 1390, 1334, 1296, 1261, 1193, 1176, 1155, 1058, 837, 862, 707, 684, 626, 8, 603 464, 443.

[0064] 1H NMR (500 MHz, CDCl 3 , δ / ppm): 8.09 (d, J =8.2 Hz, 2H), 7.27 (s, 1H),7.26 (s, 1H), ...

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Abstract

The invention discloses a 2-oxobutyrate p-toluyl hydrazone di-n-butyltin complex. The following structural formula (I) of the complex is shown in the description, wherein R is normal-butyl. The invention further discloses a preparation method of the 2-oxobutyrate p-toluyl hydrazone di-n-butyltin complex and application of the 2-oxobutyrate p-toluyl hydrazone di-n-butyltin complex in preparation of an anticancer drug.

Description

technical field [0001] The invention relates to a 2-carbonylbutyric acid p-toluylhydrazone di-n-butyltin complex and a preparation method thereof, and the 2-carbonylbutyric acid p-toluylhydrazone di-n-butyltin complex is used in the preparation of anticancer application in medicine. 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 continued in-depth research ...

Claims

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Application Information

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