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Peiminine derivative and preparation method and application thereof

A technology of peimonin B derivatives, applied in the field of chemical structure and synthesis of peiminin B derivatives, can solve the problems of low bioavailability, insoluble in water, etc., achieve simple preparation method, high conversion rate, The effect of less by-products

Pending Publication Date: 2022-02-11
CHANGCHUN UNIV OF CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Peiminin B belongs to alkaloid compounds, easily soluble in organic solvents, difficult to dissolve in water, low bioavailability, etc.

Method used

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  • Peiminine derivative and preparation method and application thereof
  • Peiminine derivative and preparation method and application thereof
  • Peiminine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment one, peiminin B derivative A 13 C-NMR spectrum and 1 H-NMR spectrum, such as figure 1 and figure 2 as shown,

[0044]

[0045] Its preparation method is: dissolve 3-furancarboxylic acid (16.81mg, 0.15mmol) and DMAP (24.43mg, 0.2mmol) in dichloromethane, stir for 10min, then add peiminin (42.96mg, 0.1mmol) and EDCI (38.34mg, 0.2mmol), stirred and dissolved, and left at room temperature for 6h. After concentration under reduced pressure, silica gel thin-layer preparation plate was purified to obtain 47.816 mg of white powder with a yield of 80%. 1 H-NMR (400MHz, CDCl 3 )δppm: 8.00 (dd, J = 1.6, 0.8Hz, 1H, 3'-H), 7.42 (t, J = 1.7Hz, 1H, 5'-H), 6.73 (dd, J = 1.9, 0.8Hz, 1H,4'-H), 4.87(tt,J=11.4,4.8Hz,1H,3-H), 1.07(d,J=7.0Hz,3H,27-H), 1.03(s,3H,21- H), 0.82(s,3H,19-H). 13 C-NMR (151MHz, CDCl 3 )δppm: 210.49 (C-6), 162.61 (C-1'), 147.69 (C-4'), 143.67 (C-3'), 119.74 (C-2'), 109.84 (C-5'), 73.14(C-3), 70.91(C-20), 70.27(C-22), 62.32(C-26), 61.77(C-18),...

Embodiment 2

[0046]Embodiment two, peiminin B derivative B 13 C-NMR spectrum and 1 H-NMR spectrum, such as image 3 and Figure 4 as shown,

[0047]

[0048] Its preparation method is: dissolve 2-naphthoic acid (25.83mg, 0.15mmol) and DMAP (24.43mg, 0.27mmol) in dichloromethane, stir for 10min, then add peiminin (42.96mg, 0.1mmol) and EDCI (38.34mg, 0.2mmol), stirred and dissolved, and left at room temperature for 6h. After concentration under reduced pressure, silica gel thin-layer preparation plate was purified to obtain 53.74 mg of light yellow powder with a yield of 78.12%. . 1 H NMR (600MHz, CDCl 3 )δppm: 8.60(t, 1H, 3'-H), 8.05(dd, J=8.6, 1.7Hz, 1H, 9'-H), 7.97(m, 1H, 8'-H), 7.88(m, 1H,4'-H), 7.86(s,1H,7'-H), 7.59(m,1H,5'-H), 7.54(m,1H,6'-H), 4.99(1H,tt, 3-H), 1.10(s, 3H, 27-H), 0.98(s, 3H, 21-H), 0.88(m, 3H, 19-H). 13 C NMR (151MHz, CDCl 3 )δppm: 209.61 (C-6), 166.26 (C-1'), 135.52 (C-11'), 132.51 (C-10'), 131.04 (C-3'), 129.41 (C-4'), 128.17(C-6'), 128.08(C-8'), 127.8...

Embodiment 3

[0049] Embodiment three, peiminin B derivative C 13 C-NMR spectrum and 1 H-NMR spectrum, such as Figure 5 and Figure 6 as shown,

[0050]

[0051] Its preparation method is: dissolve 3-indoleacetic acid (26.27mg, 0.15mmol) and DMAP (24.43mg, 0.27mmol) in dichloromethane, stir for 10min, then add peiminin (42.96mg, 0.1mmol) and EDCI (38.34mg, 0.2mmol), stirred and dissolved, and left at room temperature for 6h. After concentration under reduced pressure, silica gel thin-layer preparation plate was purified to obtain 54.78 mg of light yellow powder with a yield of 78%. 1 H-NMR (300MHz, CDCl 3 )δppm: 7.62 (dd, J = 7.9, 1.2Hz, 1H, 8'-H), 7.35 (m, 1H, 5'-H), 7.20 (m, 1H, 4'-H), 7.17 (dd, J=11.2,1.8Hz,1H,6'-H), 7.13(dd,J=8.1,7.0Hz,1H,7'-H), 4.62(tt,J=11.4,4.8Hz,1H,3-H ), 1.09 (d, J=7.8Hz, 3H, 27-H), 1.04 (s, 3H, 21-H), 0.77 (s, 3H, 19-H). 13 C NMR (151MHz, CDCl 3 )δppm: 210.49(C-6), 171.49(C-1'), 136.11(C-10'), 127.27(C-9'), 122.98(C-4'), 122.16(C-6'), 119.61(C-7'), 1...

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Abstract

The invention relates to a peiminine derivative and a preparation method and application thereof, and belongs to the field of medicinal chemistry. The preparation method comprises the following steps: dissolving 3-furancarboxylic acid, 2-naphthoic acid, 3-indoleacetic acid, Boc-valine, Boc-leucine, Boc-tryptophan, Boc-glycine, Boc-isoleucine, Boc-phenylalanine, Boc-alanine, other organic acids and 4-dimethylaminopyridine in dichloromethane, standing for 10 minutes at room temperature, adding peiminine, and finally adding 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride EDC.HCl, and reacting at room temperature for 6 hours to obtain 10 kinds of peiminine derivatives. Activity verification shows that the derivatives have a good anti-tumor effect. The preparation method disclosed by the invention has the advantages of simplicity, safety, high conversion rate, few byproducts and the like, has a good development prospect, and lays a theoretical foundation for later research.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to the chemical structure, synthesis method and application of peiminin beta derivatives. Background technique [0002] Liver cancer refers to malignant tumors derived from liver cells and hepatic cholangiocytes, and is a common malignant tumor in my country. There are many pathogenic factors of liver cancer, such as hepatitis B virus, hepatitis C virus, and liver cirrhosis caused by alcohol and drug factors, and then liver cirrhosis gradually turns into liver cancer. [0003] Primary bronchial lung cancer is referred to as lung cancer for short, and its English name is lung cancer, which refers to malignant tumors that originate in the trachea, bronchi and lung. Lung cancer is a bronchogenic carcinoma, including squamous cell carcinoma, adenocarcinoma, small cell carcinoma and large cell carcinoma. Because most of them originate from the bronchial mucosal ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61P35/00
CPCC07J71/0042A61P35/00Y02P20/55
Inventor 张辉金鑫吴楠杜延佳李晶峰李志成边学峰吕金朋兰梦高旭
Owner CHANGCHUN UNIV OF CHINESE MEDICINE
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