2- carbonyl- 2- phenyl acetic acid p-nitro benzoyl hydrazone 2-n-butyl tin complex and preparing method and application thereof

A technology of nitrobenzoylhydrazone di-n-butyltin and di-n-butyltin oxide, which is applied in the fields of tin organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve problems such as undiscovered compounds, and achieve simple preparation methods , good anticancer activity, low cost effect

Active Publication Date: 2017-01-11
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- 2- phenyl acetic acid p-nitro benzoyl hydrazone 2-n-butyl tin complex and preparing method and application thereof
  • 2- carbonyl- 2- phenyl acetic acid p-nitro benzoyl hydrazone 2-n-butyl tin complex and preparing method and application thereof
  • 2- carbonyl- 2- phenyl acetic acid p-nitro benzoyl hydrazone 2-n-butyl tin complex and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone di-n-butyltin complex:

[0043] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.181g (1.0mmol) p-nitrobenzohydrazide, 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-nitrobenzoylhydrazone di-n-butyltin acetate complex. Yield: 86.6%. Melting point: 94~96°C (dec).

[0044] Elemental analysis (C 48 h 62 N 6 o 12 sn 2 ): Calculated: C 50.02, H 5.42, N 7.29; Found: C 50.10, H 5.44, N 7.30.

[0045] FT-IR (KBr, ν / cm -1 ): 3660, 3078, 2956, 2927, 2870, 1631, 1600, 1587, 1527, 1498, 1382, 1315, 1255, 1168, 1153, 1085, 1024, 869, 852, 655, 9, 36, 90, 719 542, 520, 410.

[0046] 1 H NMR (500 MHz, CDCl 3 , δ / ppm): ...

Embodiment 2

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

[0052] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.181g (1.0mmol) p-nitrobenzohydrazide, 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 a temperature of 20~35°C to obtain a yellow transparent crystal, which is 2-carbonyl-2-phenyl p-nitrobenzoylhydrazone di-n-butyltin acetate complex. Yield: 88.5%. Melting point: 94~96°C (dec).

[0053] Elemental analysis (C 48 h 62 N 6 o 12 sn 2 ): Calculated: C 50.02, H 5.42, N 7.29; Found: C 50.10, H 5.44, N 7.30.

[0054] FT-IR (KBr, ν / cm -1 ): 3660, 3078, 2956, 2927, 2870, 1631, 1600, 1587, 1527, 1498, 1382, 1315, 1255, 1168, 1153, 1085, 1024, 869, 852, 655, 9, 36, 90, 719 542, 520, 410.

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

Embodiment 3

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

[0061] Add 0.249g (1.0mmol) di-n-butyltin oxide, 0.190g (1.05mmol) p-nitrobenzohydrazide, 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-nitrobenzoylhydrazone di-n-butyltin acetate complex. Yield: 89.0%. Melting point: 94~96°C (dec).

[0062] Elemental analysis (C 48 h 62 N 6 o 12 sn 2 ): Calculated: C 50.02, H 5.42, N 7.29; Found: C 50.10, H 5.44, N 7.30.

[0063] FT-IR (KBr, ν / cm -1 ): 3660, 3078, 2956, 2927, 2870, 1631, 1600, 1587, 1527, 1498, 1382, 1315, 1255, 1168, 1153, 1085, 1024, 869, 852, 655, 9, 36, 90, 719 542, 520, 410.

[0064] 1H NMR (500 MHz, CDCl 3 , δ / ppm)...

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Abstract

The invention discloses a 2- carbonyl- 2- phenyl acetic acid p-nitro benzoyl hydrazone 2-n-butyl tin complex in the following structural formula (I) of (img file='dest_path_image002. TIF'wi='363'he='181'/), wherein Ph is phenyl and R is normal-butyl. The invention also discloses the preparing method and application in preparing anti-cancer drugs for 2- carbonyl- 2- phenyl acetic acid p-nitro benzoyl hydrazone 2-n-butyl tin complex.

Description

technical field [0001] The invention relates to a 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone di-n-butyltin complex and a preparation method thereof, and the 2-carbonyl-2-phenylacetic acid p-nitrobenzoylhydrazone 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 fou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22A61K31/32A61P35/00
CPCC07B2200/13C07F7/2284
Inventor 蒋伍玖谭宇星邝代治张复兴朱小明庾江喜
Owner HENGYANG NORMAL UNIV
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