Diverse chiral amino boric acid, preparation method and application thereof

An aminoboronic acid, a variety of technologies, applied in chemical instruments and methods, active ingredients of boron compounds, compounds containing elements of Group 3/13 of the periodic table, etc. Problems such as poor yield of aminoboronic acid

Inactive Publication Date: 2014-01-01
SHANGHAI SAIIA CHEM PROD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0022] On this basis, the direct asymmetric synthesis method induced by chiral tert-butylsulfinamide was successfully developed by Ellman, see literature Melissa A.Beenen, Chihui An, and Jonathan A.Ellman, J.Am.Chem. According to the report of Soc..2008,130,6910-6911, the method utilizes pinacol diborane ester to react with chiral tert-butylsulfinimide under the catalysis of (ICy)CuOtBu/sodium tert-butoxide to obtain chiral Although it has the advantages of high stereoselectivity and high yield of aliphatic chain alkyl substituted imine substrates, t

Method used

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  • Diverse chiral amino boric acid, preparation method and application thereof
  • Diverse chiral amino boric acid, preparation method and application thereof
  • Diverse chiral amino boric acid, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0145] Preparation and Characterization of Aminoboronate:

[0146]

[0147] Compound(1). Use general method 1 to react.

[0148] Add 295 mg (2 mmol) of tert-butylsulfinimide Compound 1' and react for 48 hours.

[0149] The reaction mixture was purified by column chromatography on silica gel deactivated with water, and the developing solvent was chloroform / methanol system. The obtained product was a pale yellow oil (253 mg, yield: 85%) at room temperature.

[0150] 1 H-NMR(DMSO,δ,ppm):4.78(d,j=6.4,0.43H,NH),4.34(dd,j 1 =1.6Hz,j 2 =8.8Hz,1H),2.93(m,1H,CHN),2.30(m,1H),2.17(m,1H),1.97(m,1H),1.87(m,1H),1.73(m,1H) ,1.32(s,3H),1.26(s,3H),1.20(d,j=7.2Hz,3H),1.12(m,1H),1.09(s,9H),0.82(s,3H). 13 C-NMR (DMSO, δ, ppm): 85.9, 77.5, 55.5, 51.3, 38.3, 35.4, 28.8, 27.3, 26.3, 24.1, 23.1, 19.2, 19.1.

Embodiment 2

[0152]

[0153] The reaction was carried out using General Method 2.

[0154] Add 351 mg (2 mmol) of tert-butylsulfinimide Compound 2' and react for 48 hours.

[0155] The reaction mixture was purified by column chromatography on silica gel deactivated with water, and the developing solvent was chloroform / methanol system. The obtained product was a pale yellow oil (322 mg, yield: 92%) at room temperature.

[0156] 1 H-NMR(DMSO,δ,ppm):4.76(d,j=6.8Hz,1H,NH),4.34(dd,j 1 =2Hz,j 2 =8.8Hz,1H),2.82(m,1H,CHN),2.30(m,1H),2.16(m,1H),1.97(m,1H),1.87(m,1H),1.71(m,1H) ,1.56(m,2H),1.34(m,2H),1.32(s,3H),1.25(s,3H),1.13(m,1H),1.08(s,9H),0.87(t,j=7.2 Hz,3H),0.82(s,3H). 13 C-NMR (DMSO, δ, ppm): 85.9, 77.4, 55.7, 51.2, 38.3, 35.5, 35.5, 28.8, 27.3, 26.4, 24.1, 23.1, 20.1, 14.5.

Embodiment 3

[0158]

[0159] The reaction was carried out using General Method 1.

[0160] Add 351 mg (2 mmol) of imine Compound 3' and react for 48 hours. The reaction mixture was purified by column chromatography on silica gel deactivated with water, and the developing solvent was chloroform / methanol system. The obtained product was a pale yellow oil (308 mg, yield: 88%) at room temperature.

[0161] 1 H-NMR(DMSO,δ,ppm):4.73(d,j=6.8Hz,1H,NH),4.34(m,1H),2.66(t,j=6.4Hz,1H,CHN),2.32(m, 1H),2.16(m,1H),1.98(m,1H),1.87(m,2H),1.70(m,1H),1.32(s,3H),1.25(s,3H),1.18(m,1H ),1.09(s,9H),0.92(d,j=7.2Hz,6H),0.82(s,3H). 13C-NMR (DMSO, δ, ppm): 77.4, 55.9, 51.2, 38.3, 35.5, 31.2, 28.9, 27.3, 26.5, 24.2, 23.0, 20.8, 20.0.

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Abstract

The present invention discloses a diverse chiral amino boric acid, a preparation method and an application thereof, wherein the diverse chiral amino boric acid is a compound represented by a formula (I) or a formula (II). The diverse chiral amino boric acid has the following characteristics that: the library containing rich compounds with the type is provided for researches on new drugs, a yield and stereoselectivity can be increased, the preparation cost of the class 2 drugs can be reduced, the synthesis route of the class 2 drugs can be simplified, and good economic benefits are provided.

Description

technical field [0001] The present invention relates to chiral aminoboronic acid and its preparation method and application. Background technique [0002] In nature, although there are no natural aminoboronic acid compounds, the boronic acid group has a very special pseudo-decoration of natural aminocarboxylic acid, so that it has fascinating biological activity, which is similar to the characteristics of natural amino acids The aminoboronic acid compound is a compound with the following structure: [0003] [0004] Wherein: R is various substituents characteristic of natural amino acids. [0005] In recent years, α-aminoboronic acid, as the key pharmacophore of serinase antagonism, has attracted more and more attention in drug design. Due to the unique physicochemical properties and spatial structure of boron atoms (with empty p orbitals and small atomic radius), α-aminoboronic acids can be designed as various hydrolase inhibitors with important roles. For example, th...

Claims

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Application Information

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IPC IPC(8): C07F5/02A61K31/69A61P1/16A61P3/10A61P31/12A61P31/14A61P35/00
Inventor 孙智华范尔康
Owner SHANGHAI SAIIA CHEM PROD
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