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Cyrrotenohydrazide and its use as a neuraminidase inhibitor

A technology of cyproterohydrazide and neuraminidase, applied in the direction of antiviral agent, organic chemistry, etc.

Inactive Publication Date: 2018-03-16
NINGBO UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But studies have found that some virus strains are resistant to oseltamivir

Method used

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  • Cyrrotenohydrazide and its use as a neuraminidase inhibitor
  • Cyrrotenohydrazide and its use as a neuraminidase inhibitor
  • Cyrrotenohydrazide and its use as a neuraminidase inhibitor

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Experimental program
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Effect test

Embodiment 1

[0018] Preparation of Cyproterohydrazone

[0019](5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropane[c]benzopyran-7b-yl)[(R)-4-hydroxy-2-(propene-2 -yl)-2,3-dihydrobenzofuran-5-yl)methanone 2.00g (1.1mmol), dissolved in 20mL ethanol, 1.5mL content is 80% hydrazine hydrate, NaOH solid 0.25g (6.25mmol), 85 It was stirred and refluxed at ℃, tracked by TLC, washed with water after 5 hours, and dried to obtain 1.7 g of white solid with a yield of 86.4%. The melting point is 177-178.5°C. 1 H NMR (CDCl 3 , 400MHz) δ: 1.43~1.47(m, 1H, 1a-H), 1.71(s, 1H, 1-H), 1.77~1.82(m, 3H, CH 3 ), 1.96~2.05(m, 1H, 1-H), 3.01~3.10(m, 1H, 2-H), 3.34~3.39(m, 1H, 2-H), 3.64, 3.73(2×d, J =4.8Hz, 3H, CH 3 0), 3.82(s, 3H, CH 3 O), 4.08(t, J=10.6Hz, 1H, 3'-H), 4.44(t, J=10.6Hz, 1H, 3'-H), 4.92(d, J=10.8Hz, 1H, =CH 2 ), 5.09 (d, J = 10.8Hz, 1H, = CH 2 ), 5.22~5.29(m, 1H, 2′-H), 6.26, 6.37(2×d, 1H, 6-H), 6.50~6.60(m, 2H, 7′-H, 5-H), 7.45 , 7.13 (2 x m, 1H, 6'-H). ESI-MS, m / z: 422.2 (M + , 100%), 423.2...

Embodiment 2

[0021] N'-[(5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropane[c]benzopyran-7b-yl][(R)-4-hydroxyl-2- Preparation of (propen-2-yl)-2,3-dihydrobenzofuran-5-yl)methylene]acetylhydrazide

[0022] 20mL of DMF, 0.50g (1.2mmol) of cyproterine hydrazone, 0.3g of potassium carbonate and appropriate amount of molecular sieve, dissolved and added 1.5mL of acetic anhydride, reacted at 80°C, monitored by TLC, washed with brine after reacting for 3h, washed with ethyl acetate (3× 20mL) extraction, desolvation under reduced pressure to obtain 0.47g white solid, yield 84.8%. m.p.113-116°C. 1 H NMR (CDCl 3 , 400MHz) δ: 1.35~1.38(m, 1H, 1a-H), 1.77~1.82(m, 3H, CH 3 ), 1.82~2.05 (m, 3H, CH 3 CO), 2.15, 2.32(2×s, 1H, 1-H), 2.41(s, 1H, 1-H), 3.01~3.07(m, 1H, 2-H), 3.35~3.41(m, 1H, 2-H), 3.63~3.70(m, 3H, CH 3 O), 3.83(s, 3H, CH 3 O), 4.08~4.19(m, 1H, 3′-H), 4.42~4.46(m, 1H, 3′-H), 4.93(s, 1H, =CH 2 ), 5.09 (s, 1H, =CH 2 ), 5.26~5.30(m, 1H, 2′-H), 6.27~6.57(m, 3H, 6-H, 7′-H, 5-H), 7.23, 7.60(2×...

Embodiment 3

[0024] N'-[(5,6-dimethoxy-1,1a,2,7b-tetrahydrocyclopropane[c]benzopyran-7b-yl][(R)-4-hydroxyl-2- Preparation of (propen-2-yl)-2,3-dihydrobenzofuran-5-yl)methylene]propionohydrazide

[0025] Add 0.50 g (1.2 mmol) of cyrroten hydrazone, add 1 mL of propionic anhydride as a solvent, react at 25°C, monitor by TLC, and complete the reaction of the raw materials after 15 minutes. Filtration, extraction with ethyl acetate (3×20mL), and column chromatography gave 0.42g off-white solid, yield 74.2%, m.p.75-80°C, 1 HNMR (CDCl 3 , 400MHz) δ: 1.19~1.31 (m, 3H, CH 3 ), 1.35(m, 1H, 1-H), 1.78(m, 3H, CH 3 ), 1.86, 1.92(2×t, 1H, 1a-H), 1.99~2.24(m, 1H, 1-H), 2.30~2.81(m, 2H, CH 2 CO), 3.06(m, 1H, 2-H), 3.38(m, 1H, 2-H), 3.68(m, 3H, CH 3 O), 3.83(s, 3H, CH 3 O), 4.13(m, 1H, 3'-H), 4.43(m, 1H, 3'-H), 4.92(m, 1H, =CH 2 ), 5.08 (m, 1H, =CH 2 ), 5.27(m, 1H, 2′-H), 6.30~6.59(m, 3H, 6-H, 7′-H, 5-H), 7.20, 7.56(m, 1H, 6′-H), 11.72 (m, 1H, OH). ESI-MS, m / z: 477.2 (M + -1, 100%), 478.2 (M +...

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Abstract

The invention relates to application of cyclopropyl derris hydrazide to preparation of a neuraminidase inhibitor. The cyclopropyl derris hydrazide is shown in the chemical formula (I or II), wherein R is one of hydrogen, deuterium, C1 to C2 alkyl groups, C3 to C4 linear alkyl groups, C3 to C4 branched alkyl groups, C5 to C17 linear alkyl groups, C5 to C17 branched alkyl groups, halogenated C1 to C2 alkyl groups, halogenated C3 to C4 linear alkyl groups, halogenated C3 to C4 branched alkyl groups, halogenated C5 to C17 linear alkyl groups, or halogenated C5 to C17 branched alkyl groups; R1 is one of hydrogen, deuterium, C1 to C2 alkyl groups, C3 to C4 linear alkyl groups, or C3 to C4 branched alkyl groups.

Description

technical field [0001] The invention relates to a new medical application of a class of compounds, in particular to the application of cyrrotenyl hydrazide as an inhibitor of influenza virus neuraminidase. Background technique [0002] Rotenone is a compound with insecticidal activity extracted and isolated from the roots of plants such as Roten in the early days. It is one of the three traditional botanical insecticides [Insecticidal Plants and Botanical Insecticides. 2nd Edition . Beijing: China Agricultural Press, 2004]. Because rotenone has the advantages of wide insecticidal spectrum, short residual period, not easy to produce drug resistance, safe for humans and animals, and conducive to promoting ecological balance, rotenone has great development potential as a green pesticide [The application status and existing problems of rotenone. Pesticides, 2005, 44(8): 352-355]. [0003] Chinese invention patent [Cyproterohydrazide and its preparation method and application, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/06A61P31/16
CPCC07D407/06
Inventor 杨泽慧邵丹凤叶姣胡艾希
Owner NINGBO UNIVERSITY OF TECHNOLOGY