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Synthetic ion channels

An ion channel, molecular technology, applied in the prevention and/or management of diseases related to chloride channel dysfunction, preparation and use of the compound and composition, ion channel forming composition, synthetic anion channel forming, therapeutic field, Capable of solving problems such as complex structures and high molecular weights, limiting applications

Active Publication Date: 2010-03-24
VERSITECH LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many studies have focused on cation channel models, there are only a few reports on the synthesis of anion channels, especially chloride channels.
Most synthetic chloride channels generally have relatively complex structures and high molecular weights, both of which may limit their use in drug discovery

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0188] Preparation of Example 1

[0189]

[0190] Route A

[0191] Example 1 was prepared according to Scheme A above. Starting material D-2-phthalimidoxy-4-methylpentanoate (D-tert-butyl 2-phthalimidoxy-4-methylpentanoate, compound 1) was synthesized according to literature Yang et al., J . Org. Chem, 2001, 66, 7303-7312. Compound 1 is a white crystalline solid characterized by the following data: m.p.92-93°C; [α] 20 D +77.0° (c 1.01, CHCl 3 ); 1 H NMR (300MHz, CDCl 3 )δ7.85-7.81 (m, 2H), 7.78-7.74 (m, 2H), 4.74 (dd, J=8.5, 5.4Hz, 1H), 2.05-1.91 (m, 2H), 1.72-1.63 (m, 1H), 1.46(s, 9H), 1.07(d, J=6.3Hz, 3H), 1.00(d, J=6.3Hz, 3H); 13 C NMR (75MHz, CDCl 3 )δ169.13, 163.21, 134.50, 128.87, 123.53, 84.74, 83.39, 39.89, 27.82, 24.47, 22.90, 21.96; IR (CHCl 3 )3032, 1793, 1738cm -1 ; LRMS (EI, 70ev) m / z 333 (M + , 1), 278(6), 232(17), 164(15), 148(100); HRMS(EI), for C 18 h 23 NO 5 (M + ): Calculated 333.1576, Measured 333.1573.

[0192] To compound 1 (2.00g, 6.0...

Embodiment 2

[0194] Preparation of Example 2

[0195]

[0196] Route B

[0197] Example 2 was prepared according to Scheme B above. At room temperature, inject Example 1 (537mg, 1.0mmol) in CH with a syringe 2 Cl 2 (5 mL) was carefully added an equal volume of CF 3 COOH (5 mL). After stirring at room temperature for about 3 hours, the reaction mixture was concentrated in vacuo. The residue was azeotroped twice with toluene to give the free acid compound 3 as a white solid which was used directly for peptide coupling.

[0198] Add freshly distilled CH to the flask containing anhydrous compound 3 under nitrogen atmosphere 2 Cl 2 (50 mL), then HOAt (354 mg, 2.6 mmol), isobutylamine (0.21 mL, 2.1 mmol) and finally EDCI (891 mg, 3.0 mmol) were added. Stir overnight with CH 2 Cl 2 Dilute the reaction mixture. Organic layer with 5% NaHCO 3 and brine, dried over anhydrous magnesium sulfate, and concentrated. The crude oil was purified by flash column chromatography to afford 492 mg...

Embodiment 3

[0199] Preparation of Example 3

[0200]

[0201] Route C

[0202] The preparation of Example 3 was carried out according to Route C above, similar to Route B of Preparation Example 2, except that isobutylamine was replaced by decylamine. Example 3 was isolated as a colorless oil. Example 3 is characterized by the following data: [α] 20 D +34.5° (c 1.00, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ11.32(s, 2H), 8.28(br, 2H), 8.19(s, 1H), 8.05(d, J=7.5Hz, 2H), 7.52(t, J=7.5Hz, 1H), 4.38( br, 2H), 3.13-3.02(m, 4H), 1.82(m, 2H), 1.65-1.55(m, 4H), 1.42(br, 4H), 1.35-1.25(m, 28H), 0.89-0.85( m,18H); 13 C NMR (100MHz, CDCl 3 )δ172.30, 165.91, 132.05, 131.29, 129.37, 124.98, 85.31, 41.17, 39.47, 31.89, 29.55, 29.53, 29.30, 29.12, 26.91, 24.73, 23.18, 22.67, 21.79; IR, 14.Cl 3 )3446, 1662cm -1 ;LRMS(FAB)m / z704(M + , 1); HRMS(FAB), for C 40 h 71 N 4 o 6 (M + , 1): calculated value 703.5374, measured value 703.5354.

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Abstract

Provided herein are self-assembling compounds that can form ion channels in lipid bilayers or cell membranes and ion-channel-forming compositions comprising the self-assembling compounds. Also provided are methods of making and using the ion channels formed from a plurality of molecules of the self-assembling compounds. Further, provided are methods of treating or preventing conditions and diseases that are related to the dysfunction of ion channels, including chloride channels.

Description

technical field [0001] The present invention provides self-assembled compounds capable of forming ion channels in lipid bilayers or cell membranes, ion channel-forming compositions containing the compounds, pharmaceutical compositions containing the compounds, and methods for preparing and using the compounds and compositions. The invention also provides methods for forming synthetic anion channels in lipid bilayers or cell membranes. The present invention also provides methods of treating, preventing and / or managing diseases associated with chloride channel dysfunction, and methods of mediating chloride flux through liposome membranes or living cell membranes using the self-assembling compounds disclosed herein. Background technique [0002] Ion transport across cell membranes or lipid bilayers is an important biological process. Ion channels, which selectively regulate ion flow, are involved in many physiological processes including, but not limited to, neural signaling, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/14C07C239/20C07C217/48C07C217/46C07C217/42C07C225/08C07C225/14C07C225/16C07D213/63C07D213/79C07D213/81A61K31/16A61K31/215A61K31/4412A61P11/00A61P27/00A61P13/12A61P25/14A61P25/08A61P25/00A61P19/08
CPCC07D213/63C07D213/79C07D213/81C07C239/20A61P11/00A61P13/12A61P19/00A61P19/08A61P21/00A61P25/00A61P25/08A61P25/14A61P27/00A61P43/00
Inventor 杨丹李祥
Owner VERSITECH LTD
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