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Hexanary carbocycle azole like nucleoside analogue, its synthesizing process and use in anti virus and tumor thereof

A technology of nucleoside analogs and six-membered carbocyclazole, which is applied in the field of complexes of six-membered carbocyclazole nucleoside analogs and acids, can solve the problem of antiviral activity of inositol nucleoside analogs. Issues such as literature reports

Inactive Publication Date: 2007-07-18
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For now, the research on carbocyclazole nucleoside analogs is mostly focused on five-membered carbocyclic compounds, and there are few reports on other carbocyclazole nucleoside analogs, but the synthesis of inositol nucleoside analogs and its antiviral activity have not been reported in the literature

Method used

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  • Hexanary carbocycle azole like nucleoside analogue, its synthesizing process and use in anti virus and tumor thereof
  • Hexanary carbocycle azole like nucleoside analogue, its synthesizing process and use in anti virus and tumor thereof
  • Hexanary carbocycle azole like nucleoside analogue, its synthesizing process and use in anti virus and tumor thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1 : 3-O-methyl-D-inositol-5-(1'-(1',2',4'-triazole)) nucleoside and 3-O-methyl-D-inositol-4 Synthesis of -(1'-(1', 2', 4'-triazole)) nucleosides (compound numbers 1a and 1b, respectively)

[0059] (1) Synthesis of 1,2:5,6-di-O-isopropylidene-3-O-methyl-D-inositol

[0060] After adding 25mLDMF, 50mL 2,2-di-methoxypropane and 150mL acetone in a 500mL three-necked flask, add 10.0g (51.5mmol) of 3-O-methyl-D-inositol, 380mg of p-toluenesulfonic acid ( 2.0mmol) and anhydrous magnesium sulfate 9.0g, the suspension was stirred at room temperature for 16 hours, 1.0g of sodium bicarbonate was added, stirred for half an hour and then filtered, the filter residue was washed 3 times with ethyl acetate and combined with the filtrate, concentrated under reduced pressure Recrystallize with a mixed solvent of n-hexane and ether in equal proportions to obtain 12.6 g (46.0 mmol, 89%), the crude product can be directly used in the next step reaction. Melting point: 95-96°C, [α...

Embodiment 2

[0071] Example 2 : 3-O-methyl-D-inositol-5-(9'-(5'-nitroindazole)) nucleoside and 3-O-methyl-D-inositol-4-(9'- Synthesis of (5'-nitroindazole)) nucleosides (compound numbers 2a and 2b, respectively)

[0072] (1) Synthesis of 1,2:5,6-di-O-isopropylidene-3-O-methyl-D-inositol

[0073] Synthesized as in Example 1 (1) method and conditions.

[0074] (2) Synthesis of 1,2:5,6-di-O-isopropylidene-3-O-methyl-4-methanesulfonyl-D-inositol

[0075] Synthesize as embodiment 1 (2) method and condition.

[0076] (3) Synthesis of 3-O-methyl-4-methanesulfonyl-D-inositol

[0077] Synthesize as embodiment 1 (3) method and condition.

[0078] (4) Synthesis of 3-O-methyl-4,5-epoxy-D-inositol

[0079] Synthesized as in Example 1(4) method and conditions.

[0080] (5) 3-O-methyl-D-inositol-5-(9'-(5'-nitroindazole)) nucleoside and 3-O-methyl-D-inositol-4-(9 Synthesis of '-(5'-nitroindazole)) nucleosides (compound numbers 2a and 2b)

[0081] Add 352mg (2mmol) of epoxy compound and 489mg (3m...

Embodiment 3

[0085] Example 3 : Synthesis of 3-O-methyl-D-inositol-5-(1'-(1',2',4'-triazole)) nucleoside fumaric acid complex (1c)

[0086]The synthetic method of 3-O-methyl-D-inositol-5-(1'-(1', 2', 4'-triazole)) nucleoside fumaric acid complex (1c) is as follows: 3- O-methyl-D-inositol-5-(1'-(1',2',4'-triazole)) nucleoside 245mg (1mmol) and fumaric acid 124mg (1mmol) and 2ml isopropanol Mixed, the resulting mixture was stirred at 50°C until the solids were completely dissolved, then cooled at room temperature to precipitate crystals, filtered to obtain the solids, washed with ether, and dried in vacuo to obtain 269 mg, with a yield of 73%. 1 In addition to 3-O-methyl-D-inositol-5-(1'-(1',2',4'-triazole)) nucleoside signal in H NMR (DMSO), in δ(ppm) 6.185 (s, 2H) shows the signal of fumaric acid double bond hydrogen.

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Abstract

The invention relates to a group six dim carbocyclic ring azoles nucleoside analogues and their acceptable pharmaceutical compounds and their preparation methods and the application as antiviral and antineoplastic agents.The described compounds have varying degrees of inhibition effects on the human immunodeficiency virus replication and the replication of herpes virus; have varying degrees of inhibition on human lung cancer cell lines and human bladder cancer cell lines.

Description

Technical field: [0001] The present invention relates to a group of six-membered carbocyclic azole nucleoside analogs and complexes (1:1) of said six-membered carbocyclic azole nucleoside analogs and acids; the present invention also relates to said compounds and complexes Synthetic method and its application in antiviral and antitumor aspects. Background technique: [0002] In recent years, nucleoside drugs have received widespread attention as the main therapeutic drugs for viral diseases. Nucleoside drugs used to treat human immunodeficiency virus (human immunodificiency virus, HIV) and herpes simplex virus (herpes simplex virus, HSV) infection are generally HIV virus reverse transcriptase inhibitors and HSV virus deoxyribonucleic acid (deoxyribonucleic acid) acid, DNA polymerase inhibitor. Nucleoside drugs are still the most effective drugs against HIV and HSV [(a) Tang Yanbo, Li Zhuorong. Chinese Journal of Biochemical Pharmaceuticals, 2004, 25(1): 44-47; (b) Li Ziche...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08A61K31/4196A61P31/12A61P35/00
Inventor 詹天荣
Owner QINGDAO UNIV OF SCI & TECH
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