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Novel applications of pinane amine as M2 inhibitor in pharmacy

An inhibitor, pinamine technology, applied in the direction of antiviral agents, amine active ingredients, etc., can solve the problem of no biological activity and achieve the effect of inhibiting replication

Active Publication Date: 2009-10-28
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Pinamine, as a known compound, has been used as a common chemical reagent, and has not found any reports of biological activity, especially as an antiviral drug.

Method used

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  • Novel applications of pinane amine as M2 inhibitor in pharmacy
  • Novel applications of pinane amine as M2 inhibitor in pharmacy
  • Novel applications of pinane amine as M2 inhibitor in pharmacy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Embodiment 1: compound is to the inhibition experiment of influenza virus

[0075] Experimental Materials:

[0076] Influenza virus: A / WS / 33 (H1N1, amantadine resistant strain), RWSN virus (H1N1, amantadine resistant strain), A / Hong Kong / 8 / 68 (H3N2, amantadine sensitive strain). Cells: MDCK passage cells. Standard compound: amantadine, Sigma Aldrich. Cell culture: 10% FBS, DMEM, at 37 °C, 5% CO 2 under cultivation. Other reagents: TPCK trypsin (Sigma Aldrich), Hanks buffer, 7.5% BSA (Invitogen), CCK-8 (Donjindo, Japan) Test method:

[0077] 1. Take MDCK cells in good condition and press 2×10 per well 4 Inoculate a 96-well plate at 37°C, 5% CO 2 Incubate for 24 hours. Prepare two 96-well plates, one plate A / WS / 33 (H1N1, amantadine-resistant strain), and one plate A / HongKong / 8 / 68 (H3N2, amantadine-sensitive strain).

[0078] 2. Preparation of the compounds (R-pinamine and S-pinamine respectively): the compounds were dissolved in DMSO at 100 mmol / L and stored. The...

Embodiment 2

[0084] Example 2: Inhibition experiments of compounds on influenza virus M2 ion channel protein

[0085] 1. Cell preparation: Inoculate 293Trex cells with good growth status and stable expression of M2 protein (wild-type M2 and drug-resistant mutant M2) in 96-well plates at 5×10 per well, and simultaneously induce with 1 μg / ml of Zeocin, Toxic effects of compounds on cells were studied without induction. In the initial screening, two replicate holes are generally made, and the concentration gradient can be reduced, such as four. Increased during re-screening.

[0086] 2. Prepare the test compound at the corresponding concentration: prepare with PBS at pH 5.4.

[0087] 3. Treatment of inhibitors: cells were induced with tetracycline for 24 hours, and then the corresponding inhibitors were added and treated for 30 minutes.

[0088] 4. PBS treatment of cells: the culture medium in the well was blotted and removed, and 50 μl of PBS (pH 5.4 or 7.4) was added, and treated for 3 h...

Embodiment 3

[0093] Embodiment 3: the preparation of R-pinamine hydrochloride

[0094] Under an ice bath, R-pinamine (0.25g, 1.6mmol) was slowly added dropwise to the diethyl ether hydrochloride solution, stirred at room temperature to obtain a white solid precipitate, filtered, washed with diethyl ether, and drained to give a white solid R-pinamine hydrochloride 0.30 g, yield 97.4%.

[0095] 1 H NMR (400MHz, DMSO-d) δ: 0.92(s, 3H), 1.12-1.14(d, 3H, J=7Hz), 1.19(s, 3H), 1.23-1.26(d, 1H, J=7Hz) , 1.70-1.78(m, 2H), 1.90-1.91(m, 1H), 1.99-2.02(m, 1H), 2.26-2.38(m, 2H), 3.34(s, 1H), 8.22(s, 3H) . MS: 154.2[M+1] + .

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Abstract

The invention discloses applications of pinane amine with a formula I or receivable salt of the pinane amine in pharmacy which are taken as an M2 inhibitor in the preparation of drugs for preventing and curing influenza and a compound containing the pinane amine with the formula I or the receivable salt of the pinane amine in pharmacy. The pinane amine or the receivable salt or the compound of the pinane amine which is taken as an M2 ion channel protein inhibitor can block the virus reproduction and is used for curing the influenza, in particular to influenza A.

Description

technical field [0001] The patent of the invention belongs to the field of medicinal chemistry and relates to the new application of pinamine as an M2 inhibitor in pharmaceuticals. technical background [0002] Influenza (hereinafter referred to as influenza) is an acute respiratory infectious disease that seriously endangers human health. It is caused by influenza virus and has the characteristics of high prevalence, widespread prevalence and rapid transmission. There have been many worldwide influenza pandemics in history, among which the Spanish flu epidemic in 1918 was the most serious, and more than 20 million people were killed by influenza. In 2009, the "swine flu" that broke out in Mexico is now seriously threatening the lives of human beings all over the world, causing great losses to human life and social economy. [0003] At present, the main means of preventing and treating influenza are M2 ion channel protein inhibitors, neuraminidase inhibitors and influenza v...

Claims

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Application Information

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IPC IPC(8): A61K31/13A61P31/16
Inventor 胡文辉曾少高李楚芳陈凌
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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