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Crocetin amides derivative and preparation method and application thereof

A technology of saffron acid amide and saffron acid, which is applied to a class of saffron acid amide derivatives and the fields of their preparation and use, can solve the problems of limited development and utilization, difficulty in large-scale cultivation of saffron, and high cost of extraction and separation

Inactive Publication Date: 2014-04-16
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Saffron is difficult to plant in a large area, the yield of stigma is low, and the cost of extraction and separation is very high, which limits its development and utilization

Method used

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  • Crocetin amides derivative and preparation method and application thereof
  • Crocetin amides derivative and preparation method and application thereof
  • Crocetin amides derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: (2E, 4E, 6E, 8E, 10E, 12E, 14E)-N 1 , N 16 - Preparation of bis(4-fluorophenyl)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptanamide (compound 1)

[0019]

[0020] Add 1mmol crocetin to a 50mL round-bottomed flask and dissolve with 10mL organic solvent DMF or DMSO; add 2.2mmol oxalyl chloride and 2.1mmol triethylamine dropwise to the saffron solution at 0°C, and stir magnetically for 4h; Add 2.1 mmol of substituent aniline to the solution obtained in step 1 at low temperature, and stir for 8 hours with magnetic force; after the reaction, pour the reaction solution into water, extract with ethyl acetate, wash with saturated saline, and anhydrous sodium sulfate Dry, remove ethyl acetate by distillation under reduced pressure, and recrystallize with a mixed solution of ethanol and acetone (volume ratio 5:1) to obtain the final product. Brick red powder, yield 54%.m.p.254-255℃; 1 H NMR (300MHz, DMSO-d 6 )δ: 1.90(s, 6H), 2.01(s, 6H), 6.35-6.37(d, J...

Embodiment 2

[0021] Embodiment two: (2E, 4E, 6E, 8E, 10E, 12E, 14E)-N 1 , N 16 - Preparation of bis(4-chlorophenyl)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptanamide (compound 2)

[0022]

[0023] The preparation method is the same as in Example 1. Substituting 4-chloroaniline for 4-fluoroaniline, the title compound was obtained. Red brick-colored powder, yield 45%, m.p.265-266°C; 1 H NMR (300MHz, DMSO-d 6 )δ: 1.92(s, 6H), 1.99(s, 6H), 6.33-6.36(d, J=2.51Hz, 2H), 6.54-6.55(dd, J=5.64Hz, 2H), 6.57-6.60(d , J=7.17Hz, 2H), 6.86-6.72(dd, J=5.45Hz, 2H), 7.17-7.19(d, J=4.69Hz, 4H), 7.22-7.25(d, J=6.26Hz, 2H) , 7.86-7.89 (d, J=3.42Hz, 4H), 10.11 (s, 2H). MS (ESI): 547.18 (C 32 h 33 Cl 2 N 2 o 2 ,[M+H] + ).Anal.Calcd for C 32 h 32 Cl 2 N 2 o 2 : C, 70.20; H, 5.89; N, 5.12%. Found: C, 70.06; H, 5.91; N, 5.12%.

Embodiment 3

[0024] Embodiment three: (2E, 4E, 6E, 8E, 10E, 12E, 14E)-N 1 , N 16 - Preparation of bis(4-bromophenyl)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptanamide (compound 3)

[0025]

[0026] The preparation method is the same as in Example 1. Substituting 4-bromoaniline for 4-fluoroaniline, the title compound was obtained. Red brick-colored powder, yield 48%, m.p.291-292°C; 1 H NMR (300MHz, DMSO-d 6 )δ: 1.90(s, 6H), 2.02(s, 6H), 6.31-6.34(d, J=3.01Hz, 2H), 6.55-6.58(dd, J=5.61Hz, 2H), 6.57-6.59(d , J=6.21Hz, 2H), 6.85-6.89(dd, J=5.43Hz, 2H), 7.17-7.20(d, J=4.79Hz, 4H), 7.22-7.25(d, J=6.21Hz, 2H) , 7.83-7.85 (d, J=3.46Hz, 4H), 10.14 (s, 2H). MS (ESI): 635.08 (C 32 h 33 Br 2 N 2 o 2 ,[M+H] + ).Anal.Calcd for C 32 h 32 Br 2 N 2 o 2 : C, 60.39; H, 5.07; N, 4.40%. Found: C, 60.26; H, 5.08; N, 4.32%.

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Abstract

The invention relates to a crocetin amides derivative. The crocetin amides derivative is characterized by having the following general formula: (img file='DSA00000789203800011.tif' wi='1009' he='177' / ), wherein R in the formula is (img file='DSA00000789203800012.tif' wi='1529' he='751' / ). The crocetin amides derivative has obvious inhibiting effect on human lung cancer cells A549 and human gastric carcinoma cells SGC7901. Therefore, the crocetin amides derivative can be applied to preparing anti-cancer drug. The invention also discloses a preparation method of the crocetin amides derivative.

Description

technical field [0001] The invention relates to a class of crocetin amide derivatives, a preparation method thereof and an application as an anticancer drug. Background technique [0002] Saffron is a bulbous herb of the Iridaceae Saffron genus. It is native to Spain, Greece, southern European countries, Iran and other places. It is also cultivated in India and Japan. It was introduced into my country's Tibet through India, so it is called saffron. At present, the main producing areas of saffron are in countries such as Greece, Spain and Iran, and there is only a small amount of cultivation in my country. Since ancient times, saffron has been widely used in the East and the West as medicine, spice or dye. Due to its extremely low yield and time-consuming and laborious harvesting, it is expensive, known as "plant gold", and is listed as a rare and precious Chinese medicinal material in our country. Saffron has a strong effect of promoting blood circulation and removing bloo...

Claims

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Application Information

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IPC IPC(8): C07C233/15C07C233/27C07C233/09C07C231/02A61K31/167A61P35/00
Inventor 朱海亮王晓亮汤剑锋杨雨顺张雁滨张飞
Owner NANJING UNIV
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