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

A nucleoside analog, carbocyclazole technology, applied in the field of complexes of six-membered carbocyclazole nucleoside analogs and acids

Inactive Publication Date: 2011-03-16
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are few reports on analogs, but there are no reports on the synthesis and antiviral activity of inositol nucleoside analogs

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

[0061] Example 1 : 3-O-methyl-D-inositol-5-deoxy-5-(1'-(1',2',4'-triazole)) and 3-O-methyl-D-inositol Synthesis of -4-deoxy-4-(1'-(1', 2', 4'-triazole)) (compound numbers are 1a and 1b respectively)

[0062] (1) Synthesis of 1,2:5,6-di-O-isopropylidene-3-O-methyl-D-inositol

[0063] After adding 25mL DMF, 50mL 2,2-dimethoxypropane and 150mL acetone into a 500mL three-necked flask, add 10.0g (51.5mmol) of 3-O-methyl-D-inositol, 380mg (2.0 mmol) and anhydrous magnesium sulfate 9.0g, the suspension was stirred at room temperature for 16 hours, 1.0g of sodium bicarbonate was added, filtered after stirring for half an hour, the filter residue was washed 3 times with ethyl acetate and combined with the filtrate, concentrated under reduced pressure and used Equal proportions of n-hexane and diethyl ether were recrystallized from a mixed solvent 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, (c=0.021...

Embodiment 2

[0074] Example 2 : 3-O-methyl-D-inositol-5-deoxy-5-(1'-(5'-nitroindazole)) and 3-O-methyl-D-inositol-4-deoxy- Synthesis of 4-(1'-(5'-nitroindazole)) (compound numbers 2a and 2b)

[0075] (1) Synthesis of 1,2:5,6-di-O-isopropylidene-3-O-methyl-D-inositol

[0076] Synthesized as in Example 1 (1) method and conditions.

[0077] (2) Synthesis of 1,2:5,6-di-O-isopropylidene-3-O-methyl-4-O-methylsulfonyl-D-inositol

[0078] Synthesize as embodiment 1 (2) method and condition.

[0079] (3) Synthesis of 3-O-methyl-4-O-methylsulfonyl-D-inositol

[0080] Synthesize as embodiment 1 (3) method and condition.

[0081] (4) Synthesis of 3-O-methyl-4,5-epoxy-D-inositol

[0082] Synthesized as in Example 1(4) method and conditions.

[0083] (5) 3-O-methyl-D-inositol-5-deoxy-5-(1'-(5'-nitroindazole)) and 3-O-methyl-D-inositol-4- Synthesis of deoxy-4-(1'-(5'-nitroindazole)) (compound numbers 2a and 2b respectively)

[0084] Add 352mg (2mmol) of epoxy compound and 489mg (3mmol) of dry 5...

Embodiment 3

[0088] Example 3 : Synthesis of 3-O-methyl-D-inositol-5-deoxy-5-(1'-(1',2',4'-triazole)) fumaric acid complex (1c)

[0089] The synthetic method of 3-O-methyl-D-inositol-5-deoxy-5-(1'-(1', 2', 4'-triazole)) fumaric acid complex (1c) is as follows: 3-O-methyl-D-inositol-5-deoxy-5-(1'-(1',2',4'-triazole)) 245mg (1mmol) and fumaric acid 124mg (1mmol) and 2ml of isopropanol was mixed, and the resulting mixture was stirred at 50°C until the solid was completely dissolved, then cooled at room temperature to precipitate crystals, filtered to obtain the solid, washed with ether, and dried in vacuo to obtain 269mg, with a yield of 73%. 1 In addition to the 3-O-methyl-D-inositol-5-deoxy-5-(1'-(1',2',4'-triazole)) signal in H NMR (DMSO), in δ( ppm) 6.185 (s, 2H) showed 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 Patents(China)
IPC IPC(8): C07D249/08A61K31/4196A61P31/12A61P35/00
Inventor 詹天荣
Owner QINGDAO UNIV OF SCI & TECH
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