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O-aminoalcohol compounds, preparation method thereof and application thereof

An o-amino alcohol and compound technology, which is applied in the field of o-amino alcohol compounds and their preparation, can solve the problems of low content and affect inflammation resistance, and achieve the effects of simple operation and separation, high efficiency and selectivity, and cheap and easy-to-obtain raw materials.

Inactive Publication Date: 2011-11-16
XIAMEN UNIV
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0007] Endocannabinoids are distributed in many tissues in the body, and even in some immune cells, but their levels in the body are very low, which affects the resistance to inflammation

Method used

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  • O-aminoalcohol compounds, preparation method thereof and application thereof
  • O-aminoalcohol compounds, preparation method thereof and application thereof
  • O-aminoalcohol compounds, preparation method thereof and application thereof

Examples

Experimental program
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preparation example Construction

[0036] 1. Preparation of FAAH enzyme buffer:

[0037] Tris buffer (50 mM, pH 8.0) / fatty acid-free bovine serum albumin (BSA, 0.05%, as prepared).

[0038] 2. Prepare the recombinant protein of FAAH enzyme:

[0039] 1) Preparation method: The gene of FAAH enzyme was transferred into HEK-293 cells by genetic engineering method, the expressed cells were screened with G418, and then the corresponding protein was extracted from the cells after cell culture.

[0040] 2) Extraction method: cells were washed twice with PBS, 20 mM tris-HCL (pH 7.5, containing 0.32 M glucose) buffer solution was added and sonicated; the supernatant was collected by centrifugation at 800 g for 15 min. The protein concentration was measured by BCA method, diluted to 1 mg / ml, and frozen at -80 for later use.

[0041] 3. The specific steps of the activity experiment are:

[0042] 1) Add 50 μL (50 μg) of the prepared enzyme into the injection bottle, then add 2 μL DMSO or different drugs (100 μM) and reac...

Embodiment 1

[0046] Example 1 Synthesis of (2S, 3R)-2-aminododec-3-ol (1)

[0047] Step 1. L-Alanine (750 mg, 8.4 mmol), K 2 CO 3 (4.05 g, 29.6 mmol) was dissolved in acetone (16.8 mL) solvent, BnCl (3.4 mL, 29.6 mmol) was added to the mixture under ice bath, heated, and the temperature was controlled at 50-70 °C and refluxed for 15 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and the layers were separated. The upper organic phase was concentrated, and flash column chromatography (ethyl acetate: petroleum ether=1: 45) was used to obtain compound 10a (2.7 g, 7.5 mmol) in 89% yield. . [α] D 20 -88.2(c 1.0, CHCl 3 );IR(film)v max : 3061, 3024, 2936, 2835, 1729, 1494, 1448, 1375, 1189, 1140cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ: 1.32(d, J=7.1Hz, 3H), 3.54(q, J=7.1Hz, 1H), 3.61(d, J=14.0Hz, 2H), 3.81(d, J=14.0Hz, 2H) , 5.13 (d, J=12.3Hz, 1H), 5.21 (d, J=12.3Hz, 1H), 7.23-7.41 (m, 15H); 13 C NMR (100MHz, CDCl 3 )δ: 14.9, 54.4, 56.2, 66.0, 126....

Embodiment 2

[0051] Example 2 Synthesis of (2S, 3R)-2-aminotetradec-3-ol (2)

[0052] Except for step 3 and step 4, the remaining steps are the same as in Example 1.

[0053] In step 3, compound 12b was prepared from compound 11a using n-C 11 H 23 MgBr instead of n-C 9 H 19 MgBr. [α] D 20 +20.4(c 0.5, CHCl 3 ).IR(film)υ max : 3361, 2922, 2847, 1602, 1453, 1366, 1084cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ: 0.92(t, J=6.9Hz, 3H), 1.13(d, J=6.8Hz, 3H), 1.18-1.32(m, 19H), 1.68-1.78(m, 1H), 1.79(s, 1H) ), 2.71-2.77(m, 1H), 3.51(d, J=13.8Hz, 2H), 3.59-3.67(m, 1H), 3.80(d, J=13.8Hz, 2H), 7.19-7.41(m, 10H); 13 C NMR (100MHz, CDCl 3 )δ: 8.7, 14.1, 22.7, 25.9, 29.4, 29.6, 29.6, 29.6, 29.6, 29.7, 31.9, 34.3, 54.8, 57.3, 73.7, 126.9, 128.2, 128.8, 140.2ppm; MS(ESI) m / z 410 (M+H + , 100).Anal.calcd.for C 28 H 43 NO: C, 82.09; H, 10.58; N, 3.42. Found: C, 82.45; H, 10.33; N, 3.64.

[0054] In step 4, compound 2 was prepared by substituting compound 12b for 12a. [α] D 20 +12.0(c 0.5, MeOH...

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Abstract

The invention which relates to alcohol compounds provides o-aminoalcohol compounds, a preparation method thereof and an application thereof. Eight natural products of o-aminoalcohols having important physiological activities and derivatives thereof are prepared through carrying out a single stereoselective synthesis and a four-step process on an amino acid which is cheap and easily available and is treated as a raw material. A one-bottle / two-step process which is adopted in oxidative addition allows a target of single stereoselectivity to be realized and C-2 racemization not to be generated in asymmetric synthesis. The activity of the compounds as an FAAH enzyme inhibitor is analyzed through active experiments, so results provide reliable and valuable basis for medicinal development. The synthetic process which has the advantages of generality, concision, high efficiency, single selectivity, cheap and easily available raw materials, and simplicity of operation and separation of each step is suitable for industrial large-scale production.

Description

technical field [0001] The present invention relates to alcohol compounds, in particular to o-amino alcohol compounds and a preparation method and application thereof. Background technique [0002] (2S,3R)-2-Aminododec-3-ol (1) was isolated from the ascidian species Clavelina oblonga jointly by American and Brazilian scholars in 2004. It has very good antifungal activity, especially against the Candida albicans ATCC 10231 exhibits significantly more activity than clinically used antifungals (1. Kossuga, M.H.; MacMillan, J.B.; Rogers, E.W.; Molinski, T.F.; Nascimento, G.G.F.; Rocha, R.M.; Berlinck, R.G.S.J Nat Prod 2004, 67, 1879). (2S,3R)-2-aminotetradec-3-ol (xestoaminol C,2) is a reverse transcriptase inhibitor extracted from the metabolite of the Fiji cavernosa Xestospongia in 1990. It has both antiparasitic and Broad spectrum antibacterial activity (2. Jiménez, C.; Crews, P.J Nat Prod 1990, 53, 978). (2S,3R)-2-aminooctadec-3-ol (ES 285,3) was isolated from the clam Sp...

Claims

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Application Information

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IPC IPC(8): C07C215/08C07C215/10C07C213/00A61K31/133A61P25/20A61P29/00A61P25/24
Inventor 黄培强傅瑾陈碧双杨隆河叶剑良
Owner XIAMEN UNIV
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