2-(thiazol-2-yl)imino-5-(benzylidene)thiazolidin-4-one, and preparing method and applications thereof

A technology of benzylidenethiazoline and iminothiazoline is applied in the application of influenza virus neuraminidase inhibitor, and the preparation field of 2-imino-5-benzylidenethiazolin-4-one

Inactive Publication Date: 2016-10-19
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, studies have found that some virus strains are resistant to Oseltamivir

Method used

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  • 2-(thiazol-2-yl)imino-5-(benzylidene)thiazolidin-4-one, and preparing method and applications thereof
  • 2-(thiazol-2-yl)imino-5-(benzylidene)thiazolidin-4-one, and preparing method and applications thereof
  • 2-(thiazol-2-yl)imino-5-(benzylidene)thiazolidin-4-one, and preparing method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 2-[(4-tert-butylthiazol-2-yl)imino]thiazolin-4-one (2)

[0030]

[0031] 4.36g (25mmol) 4-tert-butylthiazol-2-amine, 30mL dichloromethane, stir to dissolve, add 3.45g (25mmol) anhydrous potassium carbonate, stir at room temperature for 30min, drop 2ml (25mmol) chloroacetyl chloride, Reaction 1.5h. The reaction solution was poured into ice water, extracted with dichloromethane, washed with saturated aqueous sodium carbonate, combined organic phases, dried over anhydrous sodium sulfate, precipitated, and recrystallized from ethanol to obtain 5.50 g of white solid 1, yield 87.7%, m.p.113-115 ℃.

[0032] Dissolve 2.30g (9mmol) of compound 1, 1.31g (13.5mmol) of potassium thiocyanate in 30ml of ethanol, and heat to reflux for 2.5h. After cooling, a solid was precipitated, filtered with suction, and dried to obtain 2.10 g of yellow solid 2, yield 90.0%, m.p.200-202°C. 1 HNMR (CDCl 3 , 400MHz) δ: 1.33(s, 9H, 3×CH 3 ), 3.88 (s, 2H, CH 2 ), 6.64 (s, 1H, t...

Embodiment 2

[0034] Preparation of (2E,5E)-2-(4-tert-butylthiazol-2-yl)imino-5-(3-nitrobenzylidene)thiazolin-4-one

[0035]

[0036] 35ml of acetic acid was dissolved in 0.65g of sodium acetate to prepare a buffer solution with pH=4~5, 2.0mmol of intermediate 2 and 4.0mmol of 3-nitrobenzaldehyde were added, and the reaction was heated under reflux for 10h. Cool, wash with water, filter, and recrystallize from ethanol to give yellow solid (2E,5E)-2-(4-tert-butylthiazol-2-yl)imino-5-(3-nitrobenzylidene)thiazoline-4 - Ketone, yield 66%, m.p.225-226°C. 1 HNMR (CDCl 3 , 400MHz) δ: 1.40(s, 9H, 3×CH 3 ), 6.73 (s, 1H, thiazole ring), 7.69 (t, J=8.0Hz, 1H, C 6 h 4 ), 7.86 (d, J=8.4Hz, 2H, =CH), 8.28 (d, J=8.0Hz, 1H, C 6 h 4 ), 8.49 (s, 1H, C 6 h 4 ).

Embodiment 3

[0038] Preparation of (2E,5E)-2-(4-tert-butylthiazol-2-yl)imino-5-(4-nitrobenzylidene)thiazolin-4-one

[0039]

[0040] The operation method is the same as in Example 2, compound 2 and 4-nitrobenzaldehyde react for 10 h to obtain yellow solid (2E, 5E)-2-(4-tert-butylthiazol-2-yl)imino-5-(4 -Nitrobenzylidene)thiazolin-4-one, yield 77%, m.p.270~272°C. 1 H NMR (CDCl 3 , 400MHz) δ: 1.38(s, 9H, 3×CH 3 ), 6.73 (s, 1H, thiazole ring), 7.72 (d, J=8.9Hz, 2H, C 6 h 4 ), 7.84 (s, 1H, = CH), 8.35 (d, J = 8.6Hz, 2H, C 6 h 4 ).

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PUM

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Abstract

The invention relates to 2-(thiazol-2-yl)imino-5-(benzylidene)thiazolidin-4-one shown as formulas I, II, III or IV or a mixture thereof, wherein R1 is selected from hydrogen, C1-C2 alkyl or C3-C4 straight-chain or branched chain alkyl, R2 is selected from hydrogen, C1-C2 alkyl or C3-C4 straight-chain or branched chain alkyl, X1-X5 are selected from hydrogen, C1-C2 alkyl, C3-C4 straight-chain or branched chain alkyl, nitro, amino or NHCOR, and R is selected from hydrogen, C1-C2 alkyl or C3-C4 straight-chain or branched chain alkyl. Applications of the 2-(thiazol-2-yl)imino-5-benzal thiazoline-4-one or the mixture thereof in preparation of neuraminidase inhibitors are also disclosed.

Description

technical field [0001] The present invention relates to the preparation and application of a class of novel compounds, specifically the preparation of 2-(thiazol-2-yl)imino-5-benzylidenethiazolin-4-one and its use as an inhibitor of influenza virus neuraminidase application of the agent. Background technique [0002] Avian influenza virus can cause respiratory or systemic infection of poultry. Highly pathogenic avian influenza virus can directly infect poultry, and can also directly or indirectly infect humans. Highly pathogenic avian influenza viruses are a potential risk factor for influenza in humans and pose a serious threat to human health. In the 20th century, there were four influenza pandemics in humans: the "Spanish flu" from 1918 to 1919 (H 1 N 1 subtype), the "Asian Influenza" from 1957 to 1958 (H 2 N 2 subtype), the "Hong Kong Influenza" from 1968 to 1969 (H 3 N 2 subtype) and the 1977 "Russian flu" (H 1 N 1 Subtype). Avian influenza viruses contain two...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/54A61P31/16
Inventor 胡艾希颜晓维叶姣肖梦武刘艾林连雯雯
Owner HUNAN UNIV
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