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2-carbonyl-3-phenylpropionic para hydroxybenzene carbonylhydrazone diphenyl tin complex as well as preparation method and application thereof

A technology of hydroxybenzoylhydrazone diphenyltin and phenylpropionic acid, which is applied to 2-carbonyl-3-phenylpropionic acid-p-hydroxybenzoylhydrazone diphenyltin complex and the fields of preparation and application thereof, It can solve the problems of undiscovered compounds, and achieve the effects of simple preparation method, high anti-cancer activity and good anti-cancer activity.

Active Publication Date: 2017-01-04
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-3-phenylpropionic para hydroxybenzene carbonylhydrazone diphenyl tin complex as well as preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic para hydroxybenzene carbonylhydrazone diphenyl tin complex as well as preparation method and application thereof
  • 2-carbonyl-3-phenylpropionic para hydroxybenzene carbonylhydrazone diphenyl tin complex as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonyl-3-phenylpropionic acid p-hydroxybenzoylhydrazone diphenyltin complex:

[0043] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.152g (1.0mmol) p-hydroxybenzohydrazide, 0.205g (1.1mmol) sodium phenylpyruvate and 15mL solvent in a 100mL three-necked flask protected by nitrogen Anhydrous methanol, react at 45~65°C for 8 hours, cool, filter, and control solvent volatilization and crystallization at 20~35°C to obtain yellow transparent crystals, namely 2-carbonyl-3-phenyl Diphenyltin complex of p-hydroxybenzoylhydrazone propionate. Yield: 83.6%. Melting point: 105~107°C (dec).

[0044] Elemental analysis (C 58 h 52 N 4 o 10 sn 2 ): Calculated: C 57.93, H 4.36, N 4.66; Found: C 57.90, H 4.40, N 4.62.

[0045] FT-IR (KBr, ν / cm -1 ): 3493, 3055, 3028, 2993, 1653, 1602, 1483, 1392, 1170, 848, 694, 642, 555, 520, 449.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.30 (d, J =8.7 Hz, 2H), 7.75~7.77 (m,4H), 7.51 (d, J =7.3 Hz, 2H), 7.43~7.46 (m...

Embodiment 2

[0051] Preparation of 2-carbonyl-3-phenylpropionic acid p-hydroxybenzoylhydrazone diphenyltin complex:

[0052] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.152g (1.0mmol) p-hydroxybenzohydrazide, 0.195g (1.05mmol) sodium phenylpyruvate and 35mL solvent in 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 a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-3-phenyl Diphenyltin complex of p-hydroxybenzoylhydrazone propionate. Yield: 84.5%. Melting point: 105~107°C (dec).

[0053] Elemental analysis (C 58 h 52 N 4 o 10 sn 2 ): Calculated: C 57.93, H 4.36, N 4.66; Found: C 57.90, H 4.40, N 4.62.

[0054] FT-IR (KBr, ν / cm -1 ): 3493, 3055, 3028, 2993, 1653, 1602, 1483, 1392, 1170, 848, 694, 642, 555, 520, 449.

[0055] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.30 (d, J =8.7 Hz, 2H), 7.75~7.77 (m,4H), 7...

Embodiment 3

[0060] Preparation of 2-carbonyl-3-phenylpropionic acid p-hydroxybenzoylhydrazone diphenyltin complex:

[0061] Add 0.344g (1.0mmol) diphenyltin dichloride, 0.160g (1.05mmol) p-hydroxybenzohydrazide, 0.214g (1.15mmol) sodium phenylpyruvate and 25mL solvent in 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-3-phenyl Diphenyltin complex of p-hydroxybenzoylhydrazone propionate. Yield: 82.2%. Melting point: 105~107°C (dec).

[0062] Elemental analysis (C 58 h 52 N 4 o 10 sn 2 ): Calculated: C 57.93, H 4.36, N 4.66; Found: C 57.90, H 4.40, N 4.62.

[0063] FT-IR (KBr, ν / cm -1 ): 3493, 3055, 3028, 2993, 1653, 1602, 1483, 1392, 1170, 848, 694, 642, 555, 520, 449.

[0064] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): 8.30 (d, J =8.7 Hz, 2H), 7.75~7.77 (m,4H),...

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Abstract

The invention discloses a 2-carbonyl-3-phenylpropionic para hydroxybenzene carbonylhydrazone diphenyl tin complex which has a structural formula (I) as shown in the specification, wherein Ph is phenyl. The invention also discloses a preparation method of the 2-carbonyl-3-phenylpropionic para hydroxybenzene carbonylhydrazone diphenyl tin complex and application of the 2-carbonyl-3-phenylpropionic para hydroxybenzene carbonylhydrazone diphenyl tin complex in preparation of anti-cancer drugs.

Description

technical field [0001] The invention relates to a 2-carbonyl-3-phenylpropionic acid p-hydroxybenzoylhydrazone diphenyltin complex and a preparation method thereof, and the 2-carbonyl-3-phenylpropionic acid p-hydroxybenzoylhydrazone Application of diphenyltin 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 con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61K31/32A61K31/555A61P35/00
CPCC07F7/2284
Inventor 谭宇星蒋伍玖冯泳兰庾江喜张复兴朱小明邝代治
Owner HENGYANG NORMAL UNIV