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A class of pyrazoline derivatives prepared from salicylaldehyde and preparation method thereof

A technology of pyrazolines and salicylaldehyde, which is applied in the field of pyrazoline derivatives and their preparation, can solve the problems of increased salt-forming property and increased possibility, and achieve the effect of increasing the possibility of salt-forming

Inactive Publication Date: 2016-01-20
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Increased salt formation also increases potential drug potential

Method used

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  • A class of pyrazoline derivatives prepared from salicylaldehyde and preparation method thereof
  • A class of pyrazoline derivatives prepared from salicylaldehyde and preparation method thereof
  • A class of pyrazoline derivatives prepared from salicylaldehyde and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 2-(3-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol (compound 1)

[0023]

[0024] Take 5.0mmol of p-fluoroacetophenone and 5.25mmol of salicylaldehyde and add them to a 50ml round bottom flask, add 20ml of absolute ethanol, stir magnetically for 10min under ice bath conditions to mix evenly, slowly drop 10ml of 40% NaOH solution, Magnetic stirring, react in ice bath for 0.5h, then move to normal temperature for 5h (TLC detects the progress of the reaction), after the reaction, adjust the pH to acidic (pH value is 6.0), the product is precipitated in solid form, suction filtered, and washed with cold ethanol 3 times (3ml each time), dry, and the product is recrystallized with a mixture of ethanol and acetone (volume ratio ethanol:acetone=10:1); add 2.0mmol of the above product and 2.1mmol of phenylhydrazine to a 50ml flask, and dissolve it in 20ml of anhydrous Ethanol was heated to 80°C to dissolve, and refluxed at 80°C for 2h ...

Embodiment 2

[0025] Example 2: Preparation of 2-(3-(4-chlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol (compound 2)

[0026]

[0027] The preparation method is the same as in Example 1. The p-fluoroacetophenone in Example 1 was replaced by p-chloroacetophenone to obtain the target compound in light yellow powder form. Yellowpowder, Yield54%, mp: 54-56℃. 1 HNMR (CDCl 3 , 300MHz) δ: 3.09-3.17 (dd, J 1 = 10.5Hz,J 2 =6.6Hz, 1H), 3.87-3.93 (dd, J 1 = 10.5Hz,J 2 =7.5Hz, 1H), 5.62-5.66(m, 1H), 6.77-6.79(t, J=4.5Hz, 1H), 6.84-6.88(m, 2H), 6.97-6.98(d, J=4.8Hz, 2H), 7.20-7.31(m, 4H), 7.55-7.57(d, J=5.4Hz, 2H), 7.95-7.97(d, J=5.7Hz, 2H), 10.06(m, 1H).MS(ESI ): 349.10 (C 21 h 18 ClN 2 O, [M+H] + ).Anal.CalcdforC 21 h 17 ClN 2 O: C, 72.31; H, 4.91; Cl, ​​10.16; N, 8.03; O, 4.59. Found: C, 72.13; H, 4.91; N, 8.04.

Embodiment 3

[0028] Example 3: Preparation of 2-(3-(4-bromophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenol (compound 3)

[0029]

[0030] The preparation method is the same as in Example 1. The p-fluoroacetophenone in Example 1 was replaced by p-bromoacetophenone to obtain the target compound in light yellow powder form. Yellowpowder, Yield52%, mp: 65-68℃. 1 HNMR (CDCl 3 , 300MHz) δ: 3.09-3.16 (dd, J 1 = 10.5Hz,J 2 =6.6Hz, 1H), 3.87-3.93 (dd, J 1 = 10.5Hz,J 2 =7.5Hz, 1H), 5.61-5.65(m, 1H), 6.76-6.78(t, J=4.8Hz, 1H), 6.82-6.85(m, 2H), 6.90-6.91(d, J=4.8Hz, 2H), 7.19-7.26(m, 4H), 7.59-7.61(d, J=5.4Hz, 2H), 7.66-7.68(d, J=5.4Hz, 2H), 10.04(m, 1H).MS(ESI ): 393.05 (C 21 h 18 BrN 2O, [M+H] + ).Anal.CalcdforC 21 h 17 BrN 2 O: C, 64.13; H, 4.36; Br, 20.32; N, 7.12; O, 4.07. Found: C, 64.01; H, 4.36; N, 7.13.

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Abstract

The present invention relates to pyrazoline derivatives prepared from salicylaldehyde, characterized by having the following general formula:(img file ='DSA00000789205900011.tif' wi='756' he ='453' / ),where R1 is one of the following groups:-F, -Cl,-Br,-CH3, and -OCH3,and R2 is one of the following groups: -H, -C1, -Br. The present invention discloses a preparation method of the pyrazoline derivatives.

Description

technical field [0001] The invention relates to a class of pyrazoline derivatives prepared from salicylaldehyde and a preparation method thereof. Background technique [0002] The pyrazoline skeleton structure has a variety of biological activities. It was used in the field of pesticides in the early days, and can be used as herbicides, insecticides and plant growth regulators. It was later widely used in the field of biomedicine and occupied a very important position. Its derivatives are reported to have broad-spectrum antibacterial activity and tumor inhibitory effect. In addition, the representative of this type of compound, the currently marketed drug clonidine (clonidine) is a central antihypertensive drug, which can reduce the function of peripheral sympathetic nerves by inhibiting the vasomotor center to achieve the purpose of lowering blood pressure. Rational molecular design and modification with such structures as the core, and a series of new skeleton structures ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/06
CPCC07D231/06
Inventor 朱海亮杨雨顺张雁滨王晓亮张飞杨汶汤剑锋
Owner NANJING UNIV
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