Application of lycorine compounds in the preparation of antitumor drugs

A compound, the technology of lycorine, applied in the field of lycorine compounds, can solve the problems such as the unknown mechanism of action

Inactive Publication Date: 2016-01-06
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through biological activity experiments, it was found that compounds 5, 9, 20, etc. showed very good inhibitory activity against HL-60, A549, Hela and other tumor cells, but the mechanism of action was unknown

Method used

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  • Application of lycorine compounds in the preparation of antitumor drugs
  • Application of lycorine compounds in the preparation of antitumor drugs
  • Application of lycorine compounds in the preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Example 1. Synthesis of 1-acetyl-2-phenyllycorine (1-4) and 1-acetyl-2-(4-chlorobutyryl) lycorine (1-5)

[0106]

[0107] Compounds 1-acetyl-2-phenyllycorine (1-4) and 1-acetyl-2-(4-chlorobutyryl)lycorine (1-5) were synthesized according to steps I-3 and I-4 .

[0108] 1-Acetyl-2-phenyllycorine (1-4): ESI-MS: m / z 434[M+H] + ; 1 HNMR (400MHz, CDCl 3 ): δ8.04(d, J=7.7Hz, 2H), 7.55(t, J=7.3Hz, 1H), 7.41(t, J=7.5Hz, 2H), 6.78(s, 1H), 6.60(s , 1H), 5.90(s, 2H), 5.67(s, 1H), 5.56(s, 1H), 4.21(d, J=14.1Hz, 1H), 3.65(d, J=14.1Hz, 1H), 3.54 -3.37(m, 1H), 3.11(d, J=10.5Hz, 1H), 2.99(d, J=10.5Hz, 1H), 2.71(s, 2H), 2.55(m, 1H), 1.99(s, 3H); 13 CNMR (100MHz, CDCl 3 ): δ170.0, 165.2, 146.7, 146.5, 145.8, 133.2, 132.1, 129.8, 129.8, 129.0, 128.4, 128.0, 126.5, 114.2, 107.4, 105.1, 101.1, 70.9, 69.0, 61.1, 56.4, 5 28.8, 20.9.

[0109] 1-Acetyl-2-(4-chlorobutyryl)lycorine (1-5): ESI-MS: m / z 434[M+H] + ; 1 HNMR (400MHz, CDCl 3 ): δ6.74(s, 1H), 6.57(s, 1H), 5.92(s, 2H), 5.7...

Embodiment 2

[0110] The synthesis of embodiment 2.2-TBS-lycorine (3-2) and 1-acetyl-2-TBS-lycorine (3-3)

[0111]

[0112] The compound 2-TBS-lycorine (3-2) was synthesized according to the steps of Scheme III-1 as a colorless oil.

[0113] 2-TBS-lycorine (3-3): ESI-MSm / z: 552 (M+H); 1 H-NMR (400MHz, CDCl 3 )δ: 6.79(s, 1H), 6.56(s, 1H), 5.89(s, 2H), 5.39(s, 1H), 4.37(s, 1H), 4.24(s, 1H), 4.10(d, J =14.0Hz, 1H), 3.45(d, J=14.0Hz, 1H), 3.30(m, 1H), 2.77(d, J=10.4Hz, 1H), 2.68(d, J=10.4Hz, 1H), 2.57 (m, 2H), 2.30 (m, 1H), 0.87 (s, 9H), 0.12 (s, 3H), 0.09 (s, 3H). 13 C-NMR (100MHz, CDCl 3 )δ: 146.3, 146.0, 141.8, 130.1, 128.2, 118.3, 107.6, 104.6, 100.8, 72.5, 72.0, 60.9, 57.1, 53.9, 40.8, 28.6, 25.9, 18.1, -4.4, -4.7.

[0114] The compound 1-methylsulfonyl-2-TBS-lycorine (3-3) was synthesized according to the steps of Scheme III-2 as a pale yellow solid.

[0115] 1-Methanesulfonyl-2-TBS-lycorine (3-3): ESI-MSm / z: 444 (M+H); 1 H-NMR (400MHz, CDCl 3 )δ: 6.73(s, 1H), 6.57(s, 1H), 5.91...

Embodiment 3

[0116] Example 3. Synthesis of 1-acetyl-2-carbonyl-lycorine (2-2), 2-carbonyl-lycorine (2-3) and 1-butyryl-2-carbonyl-lycorine.

[0117]

[0118] Compound 1-acetyl-2-carbonyl-lycorine (2-2) was synthesized according to the steps of scheme II-1 as a white solid.

[0119] 1-Acetyl-2-carbonyl-lycorine (2-2): ESI-MSm / z: 328 (M+H); 1 H-NMR (400MHz, CDCl 3 )δ: 6.67(s, 1H), 6.52(s, 1H), 5.94(s, 1H), 5.93(s, 1H), 5.89-5.85(m, 2H), 4.12(d, J=14.0Hz, 1H ), 3.56(d, J=14.0Hz, 1H), 3.41(m, 1H), 3.21(d, J=10.4Hz, 1H), 3.13(d, J=9.6Hz, 1H), 2.82(dm, 2H ), 2.48(q, J=8.6Hz, 1H), 1.91(s, 3H). 13 C-NMR (100MHz, CDCl 3 )δ: 192.9, 169.5, 169.1, 146.7, 146.6, 128.9, 125.2, 120.3, 107.3, 105.3, 101.0, 69.0, 62.3, 56.3, 53.2, 45.5, 30.0, 20.7.

[0120] The compound 2-carbonyl-lycorine (2-3) was synthesized according to the steps of Scheme II-2 as a pale yellow solid.

[0121] 2-Carbonyl-lycorine (2-3): ESI-MSm / z: 286 (M+H); 1 H-NMR (400MHz, CDCl 3 )δ: 6.75(s, 1H), 6.59(s, 1H), 5.99-5.89(m,...

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Abstract

The invention relates to application of a Lycorine compound in anti-tumor drugs, and also relates to application of its various optical isomers, pharmaceutically acceptable salts, solvates and prodrugs in preparation of anti-tumor drugs. The invention also relates to application of pharmaceutical compositions containing the Lycorine compound with a structure shown as formula (A) in preparation of anti-tumor drugs.

Description

technical field [0001] The present invention relates to lycorine compounds, pharmaceutical compositions, synthesis methods and preparation methods of such compounds. Specifically, the present invention provides a class of lycorine compounds, a pharmaceutical composition containing the compounds and an anti-tumor application of the compounds. Background of the invention [0002] Lycoris Herb (Lycoris Herb) belongs to the monocot class Amaryllidaceae (Amarylllidaceae), and there are more than 20 species in the world. Lycoris plants have long been used as medicinal plants to treat diseases and injuries. According to the "Compendium of Materia Medica" records: Lycoris not only has multiple functions such as detoxification, expectoration, diuresis, and vomiting, but also can be used for sore throat, carbuncle, etc. Swelling sores, scrofula, edema, etc. Lycorine is an isoquinoline alkaloid, which was first isolated from the bulb of Lycoris in 1895. It has anti-inflammatory, anti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/16A61K31/4745A61P35/00
Inventor 尚鲁庆王朋张雪李林锋尹正
Owner NANKAI UNIV
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