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Carbohydrate derivative, platinum complex with antitumour activity and its preparation method

A technology of carbohydrates and platinum complexes, applied in the direction of sugar derivatives, sugar derivatives, chemical instruments and methods, etc., can solve the problem of reducing drug activity and so on

Inactive Publication Date: 2007-07-11
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Drugs such as Carboplatin and JM216, which were invented and applied clinically, significantly reduced the toxic and side effects, but also greatly reduced the drug activity (Plat.Met.Rev.1989, 33, 162; Inorg.Chem.1995, 34, 1015)

Method used

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  • Carbohydrate derivative, platinum complex with antitumour activity and its preparation method
  • Carbohydrate derivative, platinum complex with antitumour activity and its preparation method
  • Carbohydrate derivative, platinum complex with antitumour activity and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Ethylenediamine (0.40g, 6.7mmol), methyl 2,3-anhydride-4,6-O-benylidene-α-D-mannopyranoside (4.09g, 15.5mmol) and K 2 CO 3 (0.2g) was reacted in 50mL of DMSO at 105-135°C for 10 hours, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain N,N-bis(methyl 3-deoxy-4,6-O- Benylidene-[alpha]-D-altropyranoside-3-yl)ethylenediamine 3.39 g (86%). m.p.91-3°C; [a] 21 D =+112.2(c1.0, ethanol). 1 H NMR (400MHz, CDCl 3 ): δ7.50-7.30(m, 10H), 5.47(s, 2H), 4.52(s, 2H), 4.30-4.25(m, 2H), 4.10-4.00(m, 2H), 3.95-3.90(m , 2H), 3.91(br, 2H), 3.80-3.70(m, 2H), 3.34(s, 6H), 3.22(br, 2H), 3.10-3.05(m, 2H), 2.90-2.85(m, 2H ), 2.65-2.55 (m, 2H); 13 CNMR (100MHz, CDCl 3 ): δ137.64 129.06 128.38(2C), 126.21(2C), 102.05(2C), 77.86, 70.80, 69.50, 58.69, 57.10, 55.47, 47.08, 46.11. IR(KBr): 3440, 2907, 1637, 1457, 1380, 1105, 1067, 1044, 974, 755, 670. MS (ESI) m / z (%): 589 [M + +1] (100).

Embodiment 2

[0036] Butanediamine (0.79g, 9.0mmol), methyl 2,3-anhydride-4,6-O-benylidene-α-D-mannopyranoside (5.28g, 20.0mmol) and K 2 CO 3 (0.2g) was reacted in 50mL of DMSO at 120°C for 10 hours, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain N,N-bis(methyl 3-deoxy-4,6-O-Bian Alkyne-[alpha]-D-altropyranoside-3-yl)butanediamine 5.10 g (92%). m.p.124-6°C; [a] 21 D =+131.6(c1.0, ethanol). 1 H NMR (400MHz, CDCl 3 ): δ7.55-7.30(m, 10H), 5.44(s, 2H), 4.56(s, 2H), 4.30-4.25(m, 2H), 4.15-4.00(m, 2H), 3.95-3.85(m , 4H), 3.85-3.70(m, 2H), 3.35(s, 6H), 3.33(br, 2H), 3.15-3.05(m, 2H), 2.90-2.85(m, 2H), 2.65-2.55(m , 6H).IR (KBr): 3442, 2911, 1635, 1457, 1376, 1101, 1063, 1045, 976, 753, 674. MS (ESI) m / z (%): 617 [M + +1] (100).

Embodiment 3

[0038] Hexamethylenediamine (0.71g, 6.1mmol), methyl 2,3-anhydride-4,6-O-benylidene-α-D-mannopyranoside (3.96 g, 15.0mmol) and K 2 CO 3 (0.3g) was reacted in 50mL of DMSO at 120°C for 10 hours, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain N,N-bis(methyl 3-deoxy-4,6-O-Bian Alkyne-[alpha]-D-altropyranoside-3-yl)hexamethylenediamine 3.34 g (85%). m.p.161-4°C; [a] 21 D =+127.6(c1.0, ethanol). 1 H NMR (400MHz, CDCl 3): δ7.55-7.30(m, 10H), 5.43(s, 2H), 4.52(s, 2H), 4.30-4.25(m, 2H), 4.10-4.00(m, 2H), 3.95(br, 2H ), 3.85-3.70(m, 2H), 3.33(br, 2H), 3.15-2.55(m, 14H).IR(KBr): 3440, 2908, 1633, 1458, 1375, 1106, 1063, 1044, 977, 753, 675. MS (ESI) m / z (%): 645 [M + +1] (100).

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Abstract

The invention discloses a carbohydrate derivant, complex compound and making method with coordination Pt complex compound of cancer resistant, which is characterized by the following: reacting primary diamine 2,3-anhydride-alpha-D-manna pyran glycoside to obtain the diamine; making the diamine and Pt salt to obtain the Pt complex compound of coordinated nitrogen atom; making single Pt complex compound coordinated by diamine and diPt complex compound coordinated by bridged diamine and alkali additional salt; fitting for the drug composition to treat cancer.

Description

technical field [0001] The present invention relates to a class of carbohydrate derivatives, complexes and preparation methods thereof, in particular to a class of carbohydrate-derived diamine compounds and their coordinated platinum complexes with anticancer effects, including platinum complexes The structure of the ingredients of the pharmaceutical composition and its preparation. technical background [0002] Cisplatin (cis-[PtCl 2 (NH 3 ) 2 ]) is an important class of clinical drugs for the treatment of human cancer (Inorg.Chim.Acta, 1992, 198-200, 873), but its high toxicity, drug resistance and other issues force people to look for new compounds containing nitrogen atoms. platinum complexes. Drugs such as Carboplatin and JM216, which were invented and applied clinically, significantly reduced the toxic and side effects, but also greatly reduced the drug activity (Plat.Met.Rev.1989, 33, 162; Inorg.Chem.1995, 34, 1015) . In view of the fact that carbohydrates are i...

Claims

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Application Information

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IPC IPC(8): C07H5/04C07F15/00A61K31/555A61P35/00
Inventor 施继成童庆松贾莉雷霓
Owner FUJIAN NORMAL UNIV
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