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N-acylpyrazole derritol, preparation method thereof, and application thereof

A technology for the reaction of acylpyrazole rotenol, which is applied in the field of N-acylpyrazole rotenol and its preparation and application, can solve the problem that there is no research report on the anti-neuraminidase activity of N-acylpyrazole rotenol, Achieve good anti-neuraminidase activity and high anti-neuraminidase activity

Inactive Publication Date: 2013-09-04
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no research report on N-acylpyrazole rotenol and its anti-neuraminidase activity

Method used

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  • N-acylpyrazole derritol, preparation method thereof, and application thereof
  • N-acylpyrazole derritol, preparation method thereof, and application thereof
  • N-acylpyrazole derritol, preparation method thereof, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] The preparation of embodiment 1N-acetylpyrazole rotenol

[0017]

[0018] 0.01mol (2R)-5-[7,8-dimethoxy-3,3a,4,9b-tetrahydrobenzopyrano[3,4-c]pyrazol-1-yl]-2- (propen-2-yl)-2,3-dihydrobenzofuran-4-ol, 20mL dichloromethane, 1.5g pyridine, 0.01mol acetyl chloride was added at 25°C, reacted for 15min, and the reaction solution was rotary evaporated to obtain the crude product ; Recrystallized from ethanol to obtain N-acetylpyrazole rotenol with a yield of 54.4%, m.p.210-214°C, 1 H NMR (CDCl 3 , 400MHz) δ: 1.75, 1.78 (2×s, 3H, CH 3 ), 2.37 (s, 3H, COCH 3 ), 2.99(m, 1H, 3'-H), 3.33(m, 1H, 3'-H), 3.66(s, 3H, 8-OCH 3 ), 3.79 (s, 3H, 7-OCH 3 ), 3.94(d, J=12Hz, 1H, 4-H), 4.82(d, J=10Hz, 1H, 3a-H), 4.90~4.93(m, 2H,=CH 2 , 9b-H), 5.06~5.10 (m, 2H, =CH 2 , 4-H), 5.26(q, J=7.6Hz, 1H, 2'-H), 6.46(s, 1H, 6-H), 6.49(d, J=8.4Hz, 1H, 7'-H) , 6.81 (s, 1H, 9-H), 7.49 (d, J=8.4Hz, 1H, 6'-H).

Embodiment 2

[0019] The preparation of embodiment 2N-propionyl pyrazole rotenol

[0020]

[0021] 0.01mol (2R)-5-[7,8-dimethoxy-3,3a,4,9b-tetrahydrobenzopyrano[3,4-c]pyrazol-1-yl]-2- (propen-2-yl)-2,3-dihydrobenzofuran-4-ol, 20mL dichloromethane, 1.5g pyridine, 0.01mol propionyl chloride was added at 25°C, reacted for 35min, and the reaction solution was rotary evaporated to obtain the crude product ; Recrystallized from ethanol to obtain N-propionylpyrazole rotenol with a yield of 36.6%, m.p.205-208°C, 1 H NMR (CDCl 3 , 400MHz) δ: 1.21(t, J=7.2Hz, 3H, CH 3 ), 1.74, 1.77 (2×s, 3H, CH 3 ), 2.71 (q, J=7.2Hz, 2H, COCH 2 ), 3.01(m, 1H, 3'-H), 3.32(m, 1H, 3'-H), 3.65(s, 3H, 8-OCH 3 ), 3.79 (s, 3H, 7-OCH 3 ), 3.95(dd, J=2.4Hz, J=12Hz, 1H, 4-H), 4.81(d, J=10.4Hz, 1H, 3a-H), 4.89, 4.93(2×s, 1H, 9b- H), 4.93(s, 1H, =CH 2 ), 5.09 (s, 1H, =CH 2 ), 5.09(dd, J=2.4Hz, J=12Hz, 1H, 4-H), 5.26(t, J=8.8Hz, 1H, 2'-H), 6.46(s, 1H, 6-H), 6.49 (d, J=8.0 Hz, 1H, 7'-H), 6.81 (s, 1H, 9-H), 7.49 (d, ...

Embodiment 3

[0022] The preparation of embodiment 3N-isobutyryl pyrazole rotenol

[0023]

[0024] 0.01mol (2R)-5-[7,8-dimethoxy-3,3a,4,9b-tetrahydrobenzopyrano[3,4-c]pyrazol-1-yl]-2- (propen-2-yl)-2,3-dihydrobenzofuran-4-ol, 20mL dichloromethane, 1.5g pyridine, 0.01mol isobutyryl chloride (CH 3 ) 2 CHCOCl, reacted for 35 minutes, and the reaction solution was rotary evaporated to obtain a crude product; recrystallized from ethanol to obtain N-isobutyrylpyrazole rotenol, the yield was 62.6%, m.p.185~203°C, 1 H NMR (CDCl 3 , 400MHz) δ: 1.19 (d, J=7.2Hz, 3H, CH 3 ), 1.26 (d, J=7.2Hz, 3H, CH 3 ), 1.75, 1.78 (2×s, 3H, CH 3 ), 2.99(m, 1H, 3'-H), 3.23(m, 1H, COCH), 3.34(m, 1H, 3'-H), 3.66(s, 3H, 8-OCH 3 ), 3.79 (s, 3H, 7-OCH 3 ), 3.94(dd, J=2.4Hz, J=12Hz, 1H, 4-H), 4.82(dd, J=2.4Hz, J=10.4Hz, 1H, 3a-H), 4.88~4.93(m, 2H , 9b-H, =CH 2 ), 5.02~5.09 (m, 2H, =CH 2 , 4-H), 5.09 (s, 1H, =CH 2 ), 5.27(q, J=8.0Hz, 1H, 2'-H), 6.46(s, 1H, 6-H), 6.49(d, J=8.4Hz, 1H, 7'-H), 6.82(s , 1H, 9-H)...

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PUM

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Abstract

The invention discloses N-acylpyrazole derritol with a chemical formula represented by the formula I. In the formula, R is selected from C1-C2 alkyl, C3-C4 straight-chain or branched-chain alkyl, and C6H5; X(CH2)n, X=OH, NH2, NHAc, Cl, Br, or C6H5; and n=1, 2, 3 or 4. The preparation method of N-acylpyrazole derritol comprises steps that: (2R)-5-[7,8-dimethoxy-3,3a,4,9b-tetrahydrobenzopyrano[3,4-c]pyrazole-1-group]-2-(propylene-2-group)-2,3-dihydrobenzopyran-4-phenol and acyl chloride or anhydride are subject to a reaction according to a molar ratio of 1:1, such that N-acylpyrazole derritol is obtained. The invention also provides an application of N-acylpyrazole derritol in the preparations of neuraminidase inhibitors.

Description

technical field [0001] The invention relates to N-acylpyrazole rotenol and its preparation method and application. Background technique [0002] Zhou Zhongzhen et al. described the synthesis and insecticidal and fungicidal activities of 2,3a-dihydro-benzopyran[4,3-c]pyrazol-3-one derivatives (Organic Chemistry, 2009, 29:1774). There is no research report on N-acylpyrazole rotenol and its anti-neuraminidase activity. Contents of the invention [0003] The object of the present invention is to provide N-acylpyrazole rotenol shown in structural formula I: [0004] [0005] Wherein, the R of formula I is selected from: C 1 ~C 2 Alkyl, C 3 ~C 4 Straight chain or branched chain alkyl, C 6 h 5 ;X(CH 2 ) n , X=OH, NH 2 , NHAc, Cl, Br, C 6 h 5 , n=1, 2, 3 or 4. [0006] The chemical name of N-acylpyrazole rotenol is 1-[(R)-4-hydroxy-2-(propen-2-yl)-2,3-dihydrobenzofuran-5-yl]-7, 8-Dimethoxy-3-acyl-3a,4-dihydrobenzopyrano[3,4-c]pyrazole; the numbering of its atoms i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052A61K31/4162A61P31/16
Inventor 胡艾希陈晓东叶姣
Owner HUNAN UNIV
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