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Multi-nitrogen substituted isatin derivative and synthetic method of multi-nitrogen substituted isatin derivative

A synthesis method and derivative technology are applied in the field of multi-nitrogen-substituted isatin derivatives and their synthesis, which can solve problems such as biological activity amplification, and achieve the effects of fast reaction speed, mild conditions and high purity.

Inactive Publication Date: 2012-09-26
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

From the structural analysis, the two carbonyl groups of the isatin molecule are good hydrogen bond acceptors, which interact with the aromatic rings of the aromatic rings of the isatin skeleton, which is conducive to molecular recognition and mutual synergy, and at the same time can amplify its biological activity, but at present There are no reports about this

Method used

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  • Multi-nitrogen substituted isatin derivative and synthetic method of multi-nitrogen substituted isatin derivative
  • Multi-nitrogen substituted isatin derivative and synthetic method of multi-nitrogen substituted isatin derivative
  • Multi-nitrogen substituted isatin derivative and synthetic method of multi-nitrogen substituted isatin derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of 1a~1d (taking 1a2,4,6-trimethyl-1,3-dimethylene phenylenedisatin as an example)

[0028]

[0029] Weigh isatin 1.290 g (8.76 mmol), 1.046 g (3.00 mmol) 2,4-dibromomethyl-1,3,5 triethylbenzene, K 2 CO 3 1.008 g (7.30 mmol). Dissolve 1.290 g (8.76 mmol) of isatin in 40 ml of acetonitrile and stir at room temperature until the isatin is completely dissolved and the color of the solution is orange. Add the weighed K to it 2 CO 3 At this time, the color of the solution deepened and was dark red. After stirring for half an hour, 60 mL of acetonitrile solution dissolved in 2,4-dibromomethyl-1,3,5-triethylbenzene was added. Slowly raise the temperature to 60°C. The reaction was over in about 3 hours. The recrystallized product was an orange-red solid with a yield of 89.0%. ESI-MS m / z 503.5 ([m+NH 4 ] + , 100.0%). 1 H NMR (300 MHz, DMSO) δ 7.54 (d, J = 7.4, 1.1 Hz, 2H), 7.40 (t, J = 7.8, 1.4 Hz, 2H), 7.05 (d, J = 13.6, 6.0 Hz, 4H),...

Embodiment 2

[0030] Example 2: Synthesis of 2a~2d, 3a~3d (taking 2a2,4,6-trimethyl-1,3,5-trimethylenebenzenethree isatin as an example)

[0031]

[0032]

[0033]Weigh 1.80 g of isatin, 1.40 g of 1,3,5-tribromomethyl-2,4,6-trimethylbenzene, and 1.70 g of potassium carbonate were dissolved in 100 mL of acetonitrile. After stirring at 60° C. for 4 h, the reaction was stopped. A red solid was obtained by rotary evaporation under reduced pressure, which was dissolved by adding dichloromethane, and a large amount of potassium carbonate was filtered out. The filtrate was washed three times with water, anhydrous CaCl 2 dry. Spin-dry under reduced pressure to obtain a red solid. Column chromatography separation. The developing solvent is chloroform. Recrystallization, yield: 87.0%. 1 H NMR (300 MHz, DMSO) δ 7.50 (dd, J = 7.3, 1.2 Hz, 3H), 7.18 (td, J = 7.8, 1.3 Hz, 3H), 7.01 (dd, J = 17.4, 10.0 Hz, 3H), 6.51 (d, J = 7.9, Hz, 3H), 5.00 (s, 6H), 2.37 (s, 9H), ESI-HRMSm / z 620.2 ([...

Embodiment 3

[0034] Embodiment 3: Synthesis of 4a~4d (taking 4a1,2,4,5-tetratyl tetraisatin as an example)

[0035]

[0036] Weigh 1.80 g of isatin, 1.00 g of 1,2,4,5-tetrabromomethylbenzene, and 2.00 g of potassium carbonate and dissolve them in 80 mL of DMF. After stirring at 120°C for 24h, the reaction was stopped. Rotary evaporation under reduced pressure gave a red solid, which was dissolved by adding a large amount of dichloromethane, and filtered to remove potassium carbonate. The filtrate was washed three times with water, anhydrous CaCl 2 After drying overnight, it was spin-dried under reduced pressure to obtain a red powder. Column chromatography separation, developing solvent is chloroform. After recrystallization, yield: 60.0%. 1 H NMR (300 MHz, DMSO) δ 8.05 (dd, J = 7.3, 1.2 Hz, 4H), 7.65 (td, J = 7.8, 1.3 Hz, 4H), 7.47 (dd, J = 17.4, 10.0 Hz, 4H), 7.23 (d, J = 7.9 Hz, 4H), 6.75 (s, 2H), 4.63 (s, 8H), ESI-HRMSm / z 737.32 ([M+Na] + , 100%). m.p>300°C.

[0037] ...

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Abstract

The invention discloses multi-nitrogen substituted isatin derivative and a synthetic method of the multi-nitrogen substituted isatin derivative. The multi-nitrogen substituted isatin derivative has a structure general formula of the formula (I); the synthetic method of the multi-nitrogen substituted isatin derivative comprises the steps of taking isatin derivative, dissolving into halogenated substance, refluxing reaction substrate in acetonitrile or N,N'-dimethyl formamide solvent for 2-8 hours under existence of inorganic bases such as potassium carbonate or sodium hydride, spin-drying, filtering, carrying out column chromatography and recrystallizing to obtain target compound. The synthetic method has the advantages of convenience, fast reaction speed, mild condition, simple treatment and high yield. Since the derivative has excellent antibacterial activity and acetylcholinesterase inhibitory activity, the multi-nitrogen substituted isatin derivative can be used as lead compound for resisting alzheimer's disease, and also can be applied to synthesis of pharmaceutical intermediates.

Description

technical field [0001] The invention belongs to the technical field of medicines and medicine intermediates, and specifically relates to a multi-element nitrogen-substituted isatin derivative and a synthesis method thereof. Background technique [0002] Isatin (isatin), also known as indole quinone. It is an important natural product, an endogenous active ingredient widely present in mammalian tissues and body fluids. As the precursor compound of the anticancer drug indirubin, isatin itself also has excellent pharmacological activity. Isatin and its derivatives have a variety of biological activities, and have important applications in anti-tumor, anti-virus, neuroprotection and other aspects. [0003] Alzheimer's disease is an important neurological disease. Although human beings' scientific research and exploration have developed by leaps and bounds, it is a pity that the reason for this abnormal mental activity has not yet been clarified. Although people have not fund...

Claims

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Application Information

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IPC IPC(8): C07D209/38
Inventor 黄华容郭文娇陈根庭方岩雄黄宝华张焜
Owner GUANGDONG UNIV OF TECH
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