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2-oxobutyrate di-tert-butylbenzene carbonylhydrazone diphenyhin complex and preparation method and application thereof

A technology of tert-butylbenzoylhydrazone diphenyltin and carbonylbutyric acid, which is applied in tin organic compounds, pharmaceutical formulations, organic chemical methods, etc., can solve the problems of undiscovered compounds and achieve simple preparation methods and good resistance Effect of 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 di-tert-butylbenzene carbonylhydrazone diphenyhin complex and preparation method and application thereof
  • 2-oxobutyrate di-tert-butylbenzene carbonylhydrazone diphenyhin complex and preparation method and application thereof
  • 2-oxobutyrate di-tert-butylbenzene carbonylhydrazone diphenyhin complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of p-tert-butylbenzoylhydrazone diphenyltin complex of 2-carbonylbutanoic acid:

[0043] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.192g (1.0mmol) p-tert-butylbenzohydrazide, 0.112g (1.1mmol) 2-butanuonic acid in a 100mL three-necked flask protected by nitrogen and 15mL of anhydrous methanol as a solvent, react at a temperature of 45~65°C for 8 h, cool, filter, and control the solvent volatilization and crystallization at 20~35°C to obtain a yellow transparent crystal, which is 2-carbonylbutyric acid 4-tert-Butylbenzoylhydrazone diphenyltin complex. Yield: 73.9%. Melting point: 233~235°C (dec).

[0044] Elemental analysis (C 27 h 28 N 2 o 3 Sn): Calculated: C 59.26, H 5.16, N 5.12; Found: C 59.30, H 5.20, N 5.10.

[0045] FT-IR (KBr, ν / cm -1 ): 3055, 2960, 2868, 1685, 1627, 1475, 1396, 1246, 1192, 1159, 1060, 833, 808, 729, 696, 594, 547, 495, 443, 420.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.28 (d, J =8.5 Hz, 2H), 7.81-7.83 (m,4H), 7...

Embodiment 2

[0051] Preparation of p-tert-butylbenzoylhydrazone diphenyltin complex of 2-carbonylbutanoic acid:

[0052] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.192g (1.0mmol) p-tert-butylbenzohydrazide, 0.107g (1.05mmol) 2-butyronic acid in a 100mL three-necked flask protected by nitrogen and 35mL of anhydrous methanol as a solvent, react for 5 h 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-carbonylbutyric acid 4-tert-Butylbenzoylhydrazone diphenyltin complex. Yield: 76.5%. Melting point: 233~235°C (dec).

[0053] Elemental analysis (C 27 h 28 N 2 o 3 Sn): Calculated: C 59.26, H 5.16, N 5.12; Found: C 59.30, H 5.20, N 5.10.

[0054] FT-IR (KBr, ν / cm -1 ): 3055, 2960, 2868, 1685, 1627, 1475, 1396, 1246, 1192, 1159, 1060, 833, 808, 729, 696, 594, 547, 495, 443, 420.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.28 (d, J =8.5 Hz, 2H), 7....

Embodiment 3

[0060] Preparation of p-tert-butylbenzoylhydrazone diphenyltin complex of 2-carbonylbutanoic acid:

[0061] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.202g (1.05mmol) p-tert-butylbenzohydrazide, 0.117g (1.15mmol) 2-butanonic acid in a 100mL three-necked flask protected by nitrogen 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 20~35°C to obtain a yellow transparent crystal, which is 2-carbonylbutyric acid 4-tert-Butylbenzoylhydrazone diphenyltin complex. Yield: 77.6%. Melting point: 233~235°C (dec).

[0062] Elemental analysis (C 27 h 28 N 2 o 3 Sn): Calculated: C 59.26, H 5.16, N 5.12; Found: C 59.30, H 5.20, N 5.10.

[0063] FT-IR (KBr, ν / cm -1 ): 3055, 2960, 2868, 1685, 1627, 1475, 1396, 1246, 1192, 1159, 1060, 833, 808, 729, 696, 594, 547, 495, 443, 420.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.28 (d, J =8.5 Hz, 2H), 7.81-7.83 (m,...

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Abstract

The invention discloses a 2-oxobutyrate di-tert-butylbenzene carbonylhydrazone diphenyhin complex shown in the structural formula (I). R is a phenyl group. The invention further discloses a preparation method of the 2-oxobutyrate di-tert-butylbenzene carbonylhydrazone diphenyhin complex and application of the complex to preparing anti-cancer medicine.

Description

technical field [0001] The invention relates to a 2-carbonylbutyric acid p-tert-butylbenzoylhydrazone diphenyltin complex and a preparation method thereof, and the 2-carbonylbutyric acid p-tert-butylbenzoylhydrazone diphenyltin complex Application 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 in-depth resea...

Claims

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Application Information

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