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A kind of dihydrocarbyl tin complex and its preparation method and application

A technology of dihydrocarbyl tin and complexes, which is applied in the directions of tin organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve problems such as undiscovered compounds, and achieve the effects of simple preparation method, low cost and high anticancer activity

Active Publication Date: 2018-09-14
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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  • A kind of dihydrocarbyl tin complex and its preparation method and application
  • A kind of dihydrocarbyl tin complex and its preparation method and application
  • A kind of dihydrocarbyl tin complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonylbutanoic acid salicylhydrazone di(2,4-dichlorobenzyl)tin complex:

[0043] Add 0.510g (1.0mmol) bis(2,4-dichlorobenzyl) tin dichloride, 0.152g (1.0mmol) salicylic hydrazide, 0.112g (1.1mmol) 2-butane to a 100mL three-necked flask protected by nitrogen Ketoacid and 15mL solvent anhydrous methanol, reacted at 45~65°C for 8 hours, cooled, filtered, and controlled solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely 2-carbonyl Butyric acid salicylhydrazone bis(2,4-dichlorobenzyl)tin complex. Yield: 74.3%. Melting point: 122~124°C (dec).

[0044] Elemental analysis (C 52 h 48 Cl 8 N 4 o 10 sn 2 ): Calculated: C 44.29, H 3.43, N 3.97; Found: C 44.33, H 3.40, N 3.96.

[0045] FT-IR (KBr, ν / cm -1 ): 3597, 3442, 3061, 2974, 2937, 1624, 1585, 1512, 1487, 1471, 1379, 1249, 1197, 819, 754, 727, 669, 655, 592, 534, 511, 443.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 11.16 (s, 1H), 7.59~7.61 (d, ...

Embodiment 2

[0051] Preparation of 2-carbonylbutanoic acid salicylhydrazone di(2,4-dichlorobenzyl)tin complex:

[0052] Add 0.510g (1.0mmol) bis(2,4-dichlorobenzyl) tin dichloride, 0.152g (1.0mmol) salicylhydrazide, 0.107g (1.05mmol) 2-butane to a 100mL three-necked flask protected by nitrogen Ketoacid and 35mL solvent anhydrous methanol, 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 Butyric acid salicylhydrazone bis(2,4-dichlorobenzyl)tin complex. Yield: 76.5%. Melting point: 122~124°C (dec).

[0053] Elemental analysis (C 52 h 48 Cl 8 N 4 o 10 sn 2 ): Calculated: C 44.29, H 3.43, N 3.97; Found: C 44.33, H 3.40, N 3.96.

[0054] FT-IR (KBr, ν / cm -1 ): 3597, 3442, 3061, 2974, 2937, 1624, 1585, 1512, 1487, 1471, 1379, 1249, 1197, 819, 754, 727, 669, 655, 592, 534, 511, 443.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 11.16 (s, 1H), 7.5...

Embodiment 3

[0060] Preparation of 2-carbonylbutanoic acid salicylhydrazone di(2,4-dichlorobenzyl)tin complex:

[0061] Add 0.510g (1.0mmol) bis(2,4-dichlorobenzyl) tin dichloride, 0.160g (1.05mmol) salicylhydrazide, 0.117g (1.15mmol) 2-butane to a 100mL three-necked flask protected by nitrogen gas Ketoacid and 25mL of solvent anhydrous methanol, reacted at 45~65℃ for 24 hours, cooled, filtered, and controlled solvent volatilization and crystallization at 20~35℃ to obtain yellow transparent crystals, namely 2-carbonyl Butyric acid salicylhydrazone bis(2,4-dichlorobenzyl)tin complex. Yield: 74.8%. Melting point: 122~124°C (dec).

[0062] Elemental analysis (C 52 h 48 Cl 8 N 4 o 10 sn 2 ): Calculated: C 44.29, H 3.43, N 3.97; Found: C 44.33, H 3.40, N 3.96.

[0063] FT-IR (KBr, ν / cm -1 ): 3597, 3442, 3061, 2974, 2937, 1624, 1585, 1512, 1487, 1471, 1379, 1249, 1197, 819, 754, 727, 669, 655, 592, 534, 511, 443.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 11.16 (s, 1H), 7.59~7.61 (d,...

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Abstract

The invention discloses a 2-oxobutanoic acid salicylhydrazone bis(2,4-dichlorobenzyl) tin complex. The structural formula (I) of the 2-oxobutanoic acid salicylhydrazone bis(2,4-dichlorobenzyl) tin complex is shown in the specification, wherein R is 2,4-dichlorobenzyl. The invention further discloses a preparation method of the 2-oxobutanoic acid salicylhydrazone bis(2,4-dichlorobenzyl) tin complex and an application in preparation of anti-cancer drugs.

Description

technical field [0001] The invention relates to a 2-carbonylbutyric acid salicylhydrazone bis(2,4-dichlorobenzyl)tin complex and a preparation method thereof, and the 2-carbonylbutyric acid salicylhydrazone bis(2,4-dichlorobenzyl) ) Application of tin 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 continued ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/22A61P35/00
CPCC07B2200/13C07F7/2284
Inventor 谭宇星蒋伍玖邝代治朱小明张复兴庾江喜
Owner HENGYANG NORMAL UNIV
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